WASHINGTON, D.C.— Just in time for Valentine’s Day, Historic Hotels of America®, the official program of the National Trust for Historic Preservation for recognizing and celebrating historic hotels, announced The 2026 Top 25 Historic Hotels of America® for a Romantic Proposal list. This selection of 25 authentic historic destinations celebrates the places where love stories unfold against backdrops shaped by centuries of architecture, artistry, and heartfelt hospitality. These historic hotels offer settings that feel truly unforgettable, whether couples are standing beneath hand‑painted domes, wandering through glowing winter light trails, pausing on historic bridges at sunset, or sharing a quiet moment on an art‑covered staircase.
From grand city landmarks to restored manor homes and contemporary art museum hotels, each destination on this year’s list brings its own sense of magic, creativity, and history. Together, they showcase the kinds of romantic experiences that turn a single question into a memory woven into the legacy of a remarkable place.
Woolverton Inn (1792)
Stockton, New Jersey
 | Woolverton Inn offers a tranquil, television free environment where couples can focus on each other, supported by a twelve and older guest policy that ensures a peaceful atmosphere and spectacular pastoral views of preserved farmland and grazing sheep. Northridge Restaurant adds a culinary layer to the experience with intimate farm to table dining inside a restored stone barn, while personalized hospitality from the innkeepers makes every stay feel warm, thoughtful, and tailored. The inn features countless romantic places to propose, including candlelit tables inside Northridge Restaurant, a cozy breakfast in bed moment, the graceful branches of weeping beech trees or flowering magnolias, private balconies overlooking rolling pastures, the fern garden’s stone bench beside a gentle fountain, the historic all season veranda, or the quiet perimeter trail around the sheep pasture at sunrise or sunset. The team delights in preparing the perfect surprise by staging the chosen location in advance and coordinating the entrance for a complete reveal, whether in the gardens, near the fountain, during breakfast, or on a walk by the pasture. Ring deliveries can be woven into breakfast trays, sweet treats, pasture picnics, or dessert at Northridge Restaurant for a memorable touch. The year round proposal package includes personalized staging with candles and garden flowers, assistance from experienced wedding coordinators, and photography support from the innkeepers or owner, Mario. Seasonal dining ranges from winter evenings by the soaring stone fireplace, to warm weather meals on the private deck overlooking sunset lit farmland, with options for private dining in suites, cottages, or near the wedding garden patio. Generations of couples return to Woolverton Inn and often leave heartfelt notes in the guest books, sharing how the inn’s historic charm, pastoral beauty, and enduring hospitality create a place where memories deepen over decades. Woolverton Inn dates to 1792 and was inducted into Historic Hotels of America in 2023. |
The Oaks Waterfront Hotel (1800s)
Easton, Maryland
 | The Oaks Waterfront Hotel is romantic by design, an intimate waterfront estate on 10 historic acres in Easton, Maryland, with just 11 guestrooms and suites and 4 private cottages that create a sense of privacy and calm. Couples love its blend of timeless charm and modern luxury, from sunset cruises aboard a Hinckley yacht and fireside evenings by the water, to elevated Chesapeake Bay dining at The Oak Room. With roots tracing back to a 1680 land grant and a past life as a 19th century boarding house, the hotel adds meaningful historic depth to every proposal. The most romantic place to pop the question is aboard the hotel’s 40 foot Hinckley yacht, Overcomer, during a private sunset cruise on the Miles River, where golden light, gentle breezes, and uninterrupted views create an effortlessly luxurious moment. The Oaks Waterfront Hotel team excels at coordinating seamless, personalized proposals, whether arranging a surprise cruise with champagne and a photographer, or timing a family arrival after a disguised “wine tasting” dinner. Seasonal offerings like the Romantic Winter Retreat, along with enhancements such as private boat charters, curated picnics, floral arrangements, and in room treats, allow couples to tailor their celebration. Adding to its charm, the hotel even played a role in early Hollywood history when Gary Cooper and Fay Wray stayed on site during the filming of the silent movie The First Kiss (1928), weaving another love story into the legacy of this serene waterfront retreat. The Oaks Waterfront Hotel was inducted into Historic Hotels of America in 2025. |
Omni Bedford Springs Resort (1806)
Bedford, Pennsylvania
 | With a history that dates to 1806, Omni Bedford Springs Resort is more than a destination; it is a living piece of American heritage where proposals become part of a legacy of love, elegance, and celebration. Its historic architecture, vintage charm, and classic grandeur make every moment feel monumental, especially at the Magnesia Spring Pavilion, an iconic landmark framed by lush greenery and glowing beautifully in the soft light of morning or sunset. For a more secluded, nature inspired setting, the Wedding Grotto offers a serene waterfall, natural stone, and a sense of discovery that creates an unforgettable backdrop. The resort’s associates take great pride in crafting personalized “wow” moments, from candlelit proposals at the Grotto to dessert reveals in The Crystal Room or even custom puzzles that end with the engagement ring. While there is no dedicated proposal package, the evergreen From Omni, With Love offer and special Valentine’s Day programming provide a romantic foundation for celebrations. Couples can enjoy intimate dinners in the historic Crystal Room, indulge in the luxurious A Night at the Vineyard wine pairing experience, or unwind together at Springs Eternal Spa with couples massages or private, after hours access to the Bedford Baths. Throughout the resort, romance is woven into the details, including the initials etched into the library windows in the Colonnade Building by brides to be from generations past, a whimsical reminder of the timeless love stories that have unfolded here for more than two centuries. Omni Bedford Springs Resort was inducted into Historic Hotels of America in 2008. |
Boar’s Head Resort and Birdwood Mansion (1834)
Charlottesville, Virginia
 | Boar’s Head Resort and Birdwood Mansion become especially magical during November and December, when the Winter Wander Trail of Lights transforms Heritage Lake into a glowing holiday landscape. Once a historic manor home that began as a Colonial era tavern, the estate still carries the character and architecture it developed as Birdwood, giving the entire resort a sense of history and warmth that makes romantic moments feel even more meaningful. Couples stroll along the half mile path surrounded by sparkling light displays, but the most romantic proposal spot is the Tunnel of Lights, where thousands of bulbs create a full circle of illumination that feels both whimsical and cinematic. The experience has become so popular that a second tunnel was added; one designed specifically for guests to pause and capture the moment. Knowing how many couples choose Winter Wander for their engagement, the resort created a Celebration Package that includes admission tickets, a private fire pit with s’mores, a bottle of wine or a Winter Wander beer bucket, Santa photos before December 25, personalized planning assistance, and a keepsake ornament. Many guests pair the experience with an overnight stay that includes a welcome gift, VIP passes, and balcony views of the lights. Beyond the holiday season, the resort’s expansive grounds invite couples to enjoy world class golf, outdoor activities events with Blue Ridge Mountain vistas, and moments of relaxation at the serene spa, sports club, and restaurants. Charming guestrooms and suites with modern amenities offer a peaceful retreat at the end of the day. Winter weekends also feature the Breakfast with Santa event, which offers a chef curated meal and a carriage ride that departs from just outside the restaurant. Together, these experiences create a festive and heartfelt setting where proposals feel joyful, memorable, and wrapped in the warmth of the season. Boar’s Head Resort and Birdwood Mansion dates to 1834 and was inducted into Historic Hotels of America in 2001. |
Island House Hotel (1852)
Mackinac Island, Michigan
 | For generations, Island House Hotel has been woven into the love stories of Mackinac Island, offering a rare sense of continuity as the island’s oldest operating hotel and a designated State of Michigan Historic Landmark. Romance here is shaped by history and place, from the iconic front porch and veranda overlooking the harbor, to the rocking chairs, sweeping waterfront views, and the gentle clip clop of passing horses that create a timeless, unhurried atmosphere. The porch at sunset remains the most beloved proposal spot, while the 1852 Grill Room provides an elegant indoor setting with candlelit tables, harbor views, and live piano music. Evenings by the outdoor fire pits, with stars reflecting off the water, offer another intimate moment to ask the question.The Island House Hotel team works discreetly with each guest to plan personalized proposals, from arranging flowers, photographers, and horse drawn carriage rides to coordinating celebratory dinners or in-room touches like sparkling wine and chocolate-covered strawberries. Romantic offerings such as the seasonal Romantic Retreat package and the special 2026 Once Upon an Island weekend help couples celebrate milestones with intention and ease. Classic Mackinac Island experiences like private carriage rides, scenic bike rides with picnic lunches, or the playful Ryba’s Fudge Shops Fudgemaking Experience add to the charm. What makes the Island House Hotel truly extraordinary is how often couples return to mark life’s most meaningful moments, revisiting the same rooms, views, and traditions across decades. Stories like Ron and Kathy Farnum’s, who honeymooned here in 1975 and returned for their 25th and 50th anniversaries, or couples who come back to celebrate engagements, weddings, and even their children’s birthdays, reflect the enduring magic of a place where personal histories become part of the hotel’s own. Island House Hotel dates to 1852 and was inducted into Historic Hotels of America in 2005. |
Mills House Charleston, Curio Collection by Hilton (1852)
Charleston, South Carolina
 | With cobblestone streets, rich history, and undeniable Southern charm, Charleston is one of the most romantic cities in the country. Mills House Charleston, Curio Collection by Hilton, an iconic pink landmark in the heart of the historic district, has been a beloved backdrop for love stories for more than 170 years. The hotel blends historic grandeur with contemporary comfort, from its intimate courtyard designed by Loutrel Briggs and beautifully appointed guestrooms, to the signature restaurant, Iron Rose, and the rooftop pool and bar of The Terrace. Many couples choose to get engaged in the serene courtyard or on the rooftop terrace, where soft evening light, lush greenery, and the gentle hum of downtown Charleston create a naturally intimate mood. The hotel team works closely with each “asker” to plan seamless and creative moments, whether revealing the ring through an elevated champagne presentation at Iron Rose or timing a dessert surprise perfectly with the ambiance. The Mills House also offers its Southern Sweethearts package, which includes a two night stay, welcome champagne, fresh florals, a dessert amenity for two, and dining credit to enjoy at Iron Rose. Over the years, countless couples have celebrated engagements, anniversaries, and milestones here, often returning to the place where their story began. Iron Rose provides a romantic dining experience with its courtyard setting, warm hospitality, and elevated Lowcountry inspired cuisine, and the team can arrange private, customized dinners for special occasions. Additional romantic experiences include private rooftop moments, curated champagne and dessert pairings, floral styling from select partners, personalized signage, room surprises, and thoughtful itinerary planning that help create celebrations that feel effortless, intimate, and unforgettable. Mills House Charleston, Curio Collection by Hilton dates to 1852 and was inducted into Historic Hotels of America in 2024. |
The Mission Inn Hotel & Spa (1876)
Riverside, California
 | The Mission Inn Hotel & Spa, built over generations by Frank Miller, was shaped by a belief in beauty, craftsmanship, and storytelling. In a world where many moments feel fleeting, The Mission Inn Hotel & Spa offers something rare: a setting that is intentional, storied, and profoundly romantic, making a proposal feel not only magical, but timeless. World leaders, artists, and visionaries have walked its halls, and a “yes” here becomes part of a much larger narrative woven through more than a century of meaningful moments. The Atrio Courtyard and the Spanish Patio are among the most romantic places to propose, each offering iconic architecture and breathtaking ambiance. The hotel also features unforgettable landmarks such as the arched Campanario, warm and inviting restaurants, and intimate spaces like the Alhambra Courtyard on the top floor. The Atrio Courtyard, located just outside the St. Francis of Assisi Chapel, is surrounded by Tiffany stained glass windows, handcrafted fourteen foot-tall doors, and the Bacchus Fountain, creating a setting that feels undeniably romantic. Sunset seating in the Spanish Patio at the Mission Inn Restaurant or a candlelit dinner at Duane’s Prime Steaks and Seafood also provide perfect moments to ask the question. The hotel has been part of many love stories, including Bette Davis’s 1945 wedding in the chapel, Richard Nixon’s 1940 wedding to Pat Ryan, and the honeymoon of Ronald and Nancy Reagan, all of which contribute to its rich and storied legacy. The Mission Inn Hotel & Spa dates to 1876 and was inducted into Historic Hotels of America in 1996. |
Napa River Inn (1884)
Napa, California
 | Napa River Inn, a historic boutique inn on the banks of California’s Napa River, embodies romance with its historic ambiance, luxury service, and proximity to world class dining, shopping, and experiences. Napa Valley is one of the world’s most romantic destinations, and the inn offers romantic getaway packages with wine amenities, gondola cruises on the Napa River, and access to more than 20 nearby tasting rooms and restaurants. While there are many beautiful and memorable places to propose in Napa Valley, the most romantic is on a gondola on the Napa River. This proposal combines the timeless romance of an authentic Venetian gondola with California Wine Country, juxtaposing Italian tradition against the backdrop of the natural Napa River. A popular location to become engaged, the experience engages all the senses: the gentle glide of the gondola, the sound of water lapping against the hull, a singing gondolier providing ambiance, wine to toast the moment, and stunning riverside views of northern California’s scenery and wildlife. Plus, unlike restaurants or overlooks, all gondola cruises are completely private. Couples float on a serene stretch of river with only the gondolier, who can discreetly fade into the background. This combination of Old-World romance, Wine Country sophistication, natural beauty, and privacy makes it unlike any other proposal setting in America. Established in 1884 as a grain mill and converted into a luxury inn in 2000, Napa River Inn was inducted into Historic Hotels of America in 2004. |
Eagles Mere Inn (1887)
Eagles Mere, Pennsylvania
 | Eagles Mere Inn offers a romantic escape defined by cozy fireplaces, beautifully remodeled guestrooms, warm hospitality, and the serene natural beauty of its historic village setting. Couples find endless opportunities for connection, whether strolling to the lake at sunset, wandering the quiet Village Green, or choosing intimate proposal spots like the Outlet Pond, the beach, or one of the inn’s own charming nooks. The entire town provides a peaceful, storybook backdrop where special moments feel private and uninterrupted, and the staff delights in helping bring those moments to life, from decorating rooms for surprise engagements to saving the day during weddings with thoughtful, behind the scenes support. Valentine’s Day weekend brings added romance with vow renewals from the Mayor of Eagles Mere, and a special candlelit dinner for two. Guests may request personalized touches like congratulatory digital photo displays to make celebrations even more meaningful, or flowers placed in their room upon arrival. Many couples return year after year to reminisce about engagements, weddings, and milestone anniversaries, drawn back by the inn’s timeless charm and the memories they have made in this beloved mountain village. Eagles Mere Inn dates to 1887 and was inducted into Historic Hotels of America in 2021. |
Casa Monica Resort & Spa (1888)
St. Augustine, Florida
 | Casa Monica Resort & Spa is inherently romantic, blending rich history, dramatic Spanish Baroque Revival and Moorish Revival-style architecture, and intimate experiences designed for connection. Built in 1888 and set in the heart of St. Augustine’s historic district, the hotel surrounds couples with cobblestone streets, horse drawn carriages, centuries old landmarks, and bayfront views that create a cinematic backdrop for a proposal. Favorite locations include the grand stairway leading to the pool, the Anastasia Suite with views of the Lightner Museum and Flagler College, a horse drawn carriage stop in front of the hotel, and the velvet lined private dining rooms of Cordova Coastal Chophouse & Bar. The team specializes in bespoke proposal planning, from champagne reveals historically inspired ring deliveries or personal touches involving children or pets. Romantic dining ranges from private candlelit dinners by the pool to intimate spaces like the Wine Room and Sultan’s Room of Cordova, as well as curated alfresco dinners amid lantern lit downtown St. Augustine. Casa Monica is known for immersive celebrations, including carriage rides with champagne, personalized proposal signage, and poolside dinners with candlelight and live music. One of the hotel’s most heartfelt stories involved a couple who arrived hoping to marry without family present; the staff created a deeply personal ceremony, a private rose petal dinner, and a carriage ride before transforming their suite into a honeymoon retreat. They now return every year to celebrate their anniversary. Casa Monica Resort & Spa was inducted into Historic Hotels of America in 2001. |
Ledges Hotel (1890)
Hawley, Pennsylvania
 | Ledges Hotel carries the soul of its past within its walls. Once a bustling 1890s glass factory, it has been transformed into a sanctuary where history, nature, and modern design meet in a way that feels both intentional and quietly romantic. The bluestone building rises beside Paupack High Falls, and the sound of rushing water becomes part of the experience, echoing through guestrooms and gathering spaces filled with adaptive reuse furnishings and views of the river gorge. Proposals here feel like moments suspended in time. Couples wander the tiered decks overlooking the falls, choosing the secluded Stargazer Deck high above the gorge or the wide open Great Deck where the waterfall stretches out below. Each season paints the landscape differently: winter turns the falls into shimmering ice, spring brings budding trees and rushing water, summer is lush and cool, and autumn wraps the gorge in vibrant color. Hidden corners like “the ruins,” with its bluestone walls and secret garden atmosphere, offer intimate spaces for a quiet question. Inside, Glass – wine.bar.kitchen sets the stage for candlelit proposals over an unforgettable meal. The staff loves helping craft these moments, arranging rose petal paths, floral arches, champagne toasts, and photography to capture every detail. February brings the Romance by the Falls package, complete with flowers, Moka Origins chocolate, bubbly, and a dining credit, while spa experiences at the Art Deco inspired Vault 240 add another layer of indulgence. At Ledges Hotel, proposals unfold against the timeless rhythm of the falls, creating memories that feel rooted in place and impossible to forget. Ledges Hotel dates to 1890 and was inducted into Historic Hotels of America in 2013. |
Hotel Colorado (1893)
Glenwood Springs, Colorado
 | Hotel Colorado, fondly known as the “Grand Dame of the Rockies,” has been a beloved Glenwood Springs icon since 1893, welcoming travelers from around the world who came to soak in the healing mineral hot springs. Often called the town’s living room, the hotel’s grand ballrooms, cozy nooks, and crackling fireplaces have hosted generations of couples celebrating life’s most meaningful moments. Following more than $8 million in floor to ceiling renovations, every guestroom now features custom Italian villa inspired furnishings, top tier beds and linens, Turkish cotton robes, and luxury bath amenities. Couples have three especially romantic places to propose: beside the bubbling fountain and koi pond in the Victorian courtyard garden, on a Bell Tower Suite balcony overlooking Glenwood Springs, or before one of the original stone fireplaces in the grand lobby. Certified wedding planner Alta Otto helps coordinate every detail, and the hotel’s Proposal Package includes a personal proposal planner, champagne, flowers, a Signature Suite stay, and chocolate covered strawberries. Baron’s Restaurant elevates the experience with carefully crafted dishes, from top choice beef to fresh trout, served amid the soothing sound of an indoor waterfall or alfresco in the landscaped courtyard during warmer months. Beyond the hotel, Glenwood Springs offers three romantic hot springs experiences within walking distance, including the world famous Glenwood Hot Springs with its Grand Pool, Therapy Pool, and intimate Yampah Mineral Baths. Couples can also unwind at Iron Mountain Hot Springs, with an adults-only Premier Access area that is a sanctuary along the Colorado River, featuring pools inspired by mineral waters from around the world. No romantic getaway is complete without a couples massage and time in the geothermal vapor caves at Yampah Spa and Vapor Caves, a serene retreat perfect for relaxation and rejuvenation. Hotel Colorado dates to 1893 and was inducted into Historic Hotels of America in 2007. |
The Pfister Hotel (1893)
Milwaukee, Wisconsin
 | The Pfister Hotel surrounds guests with old world elegance, where warm lighting, Victorian artwork, and historic architectural details invite couples to slow down and savor each luxurious moment. For more than a century, its corridors, portraits, and grand gathering spaces have witnessed countless celebrations, giving every proposal a sense of legacy and emotional weight. Many couples choose to begin the next chapter of their love story beneath the lobby’s domed ceiling mural, originally created for the hotel’s 100th anniversary and restored in 2024, or at the foot of the grand staircase flanked by the hotel’s iconic lions, while live piano music or soft jazz fills the space. Others are drawn to Blu, the hotel’s signature cocktail lounge, where panoramic views of downtown Milwaukee and Lake Michigan turn a sunset proposal into something cinematic. The concierge team coordinates timing, surprise moments, and ring reveals, including a beloved tradition in which champagne arrives with the ring presented under a cloche or on a dessert plate, revealed by a simple, handwritten note. Engagement weekends feel fully curated through packages such as the Celebration Package, the Luxury Getaway, and the All-Inclusive Stay, which offer champagne, dining credits, spa treatments, and late night desserts. Seasonal experiences like Hearts Above the City at Blu add even more romance, with skyline views, live music, petite desserts, and Veuve Clicquot for the toast. Mason Street Grill provides intimate or private dining options paired with live jazz, creating a perfect setting for a candlelit proposal. One especially memorable moment involved a guest who arranged for Doc Hollander to play the couple’s favorite love song on the lobby piano as he proposed before the grand marble staircase, a scene that captures the timeless charm and enduring romance that defines The Pfister Hotel. The Pfister Hotel was established in 1893 and was inducted into Historic Hotels of America in 1994. |
XV Beacon (1903)
Boston, Massachusetts
 | Tucked within Boston’s historic Beacon Hill neighborhood, XV Beacon offers an intimate and luxurious setting that has earned its reputation as one of the city’s most celebratory hotels for romantic milestones. Couples often choose to propose in the hotel’s atmospheric Wine Cellar before enjoying a private dinner for two, or on the exclusive seasonal rooftop deck with sweeping views of the city. Beyond the hotel, the surrounding cobblestone streets create a naturally romantic backdrop, with Acorn Street standing out as one of the most photographed and charming locations in the country for a picture perfect moment. Guests benefit from the hotel’s dedicated 24 hour concierge team, who excel at crafting personalized engagement experiences, whether that includes arranging the Romance on the Hill package, securing a table at the award winning Mooo…. Beacon Hill, or preparing an in room dining setup beside a glowing guestroom fireplace. The Wine Cellar can also be reserved for an ultra private dining experience, complemented by curated off site activities, custom welcome amenities, and thoughtful romantic touches during turndown service. XV Beacon’s blend of elegance, intimacy, and attentive service makes it an unforgettable destination for proposals and celebrations of love. XV Beacon dates to 1903 and was inducted into Historic Hotels of America in 2016. |
Castle Hill Resort and Spa (1905)
Cavendish, Vermont
 | Castle Hill Resort and Spa carries a lasting sense of meaning, where history, nature, and romance come together effortlessly. Built in 1905, the mansion immediately sets a timeless, intentional tone that makes a proposal here feel deeply special. Each season adds its own charm: spring and summer bring blooming gardens and a babbling fountain, fall surrounds the estate with rich foliage and historic backdrops, and winter offers candlelit pathways, snow covered mountain views, and the warm glow of the fireside library. Inside, the mahogany walls, crystal chandeliers, ornate plaster ceilings, grand staircase, and roaring porcelain fireplace create an atmosphere of classic elegance. The team works closely with each “asker” to personalize every detail, whether placing the ring on a heart shaped dessert plate with “Will You Marry Me?” written in chocolate, tucking it into a glass of champagne, or preparing a guestroom with rose petals and chocolate covered strawberries. Engagement packages are available year round and can include a one night stay, a romantic gourmet dinner for two, long stem roses, champagne, and coordination with a preferred local photographer. Guests may also arrange a private candlelit dinner in the award winning historic dining room, where mahogany walls, plaster ceilings, and crystal chandeliers create a cozy, intimate setting. From live music and flowers to horse drawn carriage rides, personalized proposal signage, photography, and fully customized planning, the Castle Hill Resort and Spa team can bring nearly any vision to life, ensuring each proposal feels personal, memorable, and worthy of the moment. Castle Hill Resort and Spa was inducted into Historic Hotels of America in 2007. |
Hayes Mansion San Jose, Curio Collection by Hilton (1905)
San Jose, California
 | Hayes Mansion San Jose, Curio Collection by Hilton offers a naturally romantic setting where California warmth meets the elegance of a historic estate that dates to 1905. Its grand architecture, sweeping lawns, and lush gardens create an atmosphere that feels both intimate and enduring, making a proposal here feel like the beginning of a story rooted in more than a century of celebrations. One of the most romantic places to pop the question is the East Lawn, framed by palm trees, banana trees, and historic stonework that glows beautifully at sunset, while the mansion’s historic parlors provide refined indoor spaces with fireplaces and classic décor. The team at Hayes Mansion San Jose, Curio Collection by Hilton is known for discreet, thoughtful coordination, from arranging heart shaped floral arches with petals and candlelight, to crafting personalized setups that ensure the ring appears at exactly the right moment. Engagement celebrations often continue on the Westwood Patio, an intimate glass ceilinged, string lit venue ideal for gatherings of up to 75 guests, where the culinary team creates custom menus tailored to each couple’s vision. Hayes Mansion San Jose, Curio Collection by Hilton can further enhance the experience with live or background music, floral design, champagne service, and personalized room amenities that extend the celebration long after the proposal. Many guests share that engagements here feel “meant to be,” as the estate has hosted generations of milestones, and returning years later only deepens the meaning of beginning their story in such a historic and welcoming place. Hayes Mansion San Jose, Curio Collection by Hilton was inducted into Historic Hotels of America in 2019. |
Keswick Hall (1912)
Charlottesville, Virginia
 Photo by Aaron Watson | Keswick Hall’s historical beauty, from its Italianate-style architecture with creamy stucco and terra cotta roofs, to its lush gardens and sweeping views of the Blue Ridge Mountains, creates an effortlessly romantic setting for unforgettable moments. Couples have several stunning proposal locations to choose from, including the Horizon Pool overlooking the golf course at sunset, and the fairway, with the hotel as a dramatic backdrop. The Guest Experience Coordinator excels at crafting personalized proposal experiences, arranging everything from rose petal turndowns and champagne amenities, to unique touches such as falconry. The seasonal Celebration Package and Romance Package are available in January and February, offering elevated ways to mark the occasion. Marigold by Jean Georges provides an intimate dining experience with outdoor seating and fireplaces when the weather allows, while the Library beside Crawford’s Bar offers a cozy and elegant alternative. Guests can also enjoy Keswick Hall’s exclusive fleet of BMW vehicles, including a convertible perfect for a scenic drive to a Blue Ridge overlook. What makes Keswick Hall especially meaningful is the number of families who have become engaged, married, or celebrated across generations on the estate, weaving the hotel into their lasting love stories. Keswick Hall dates to 1912 and was inducted into Historic Hotels of America in 2015. |
21c Museum Hotel St. Louis (1926)
St. Louis, Missouri
 | 21c Museum Hotel St. Louis offers a proposal setting that feels both artistic and deeply rooted in the city’s history. Located in a beautifully restored former YMCA building from the 1920s, the hotel blends contemporary art with historic architecture, creating an atmosphere that feels vibrant, creative, and full of character. Couples are often drawn to the lush central staircase wrapped in The Way Out West, a site specific installation by artists David Allen Burns and Austin Young of Fallen Fruit. The piece transforms the stairwell into a collage of flowers, plants, historic artifacts, and native Missouri wildlife, creating an otherworldly backdrop that feels perfect for a romantic, unforgettable moment. Guests also love the hotel’s ability to personalize the experience, whether through surprise musicians in the art gallery, bottles of bubbly delivered to the guestroom, or chocolates waiting after dinner. Packages such as Love Birds, which includes a dining credit at Idol Wolf along with sparkling wine and chocolates, and Pampered Penguin, which adds a massage at the wellness club, help couples craft a full celebration. Idol Wolf’s moody dining room, with its star like ceiling lights and intimate booths, is a favorite for romantic dinners, and private dining, with a fireplace and rich curtains, offers an elevated option. Guests seeking something truly dramatic can even rent gallery spaces in the museum for private events surrounded by contemporary art. The hotel often adds thoughtful touches for couples who become part of its story, including sending souvenir ceramic penguins to those who get engaged at the hotel. Many return for future milestones, including the first couple married at 21c Museum Hotel St. Louis in 2023, whose framed wedding photo still hangs in the office as a reminder of the love stories that continue to unfold within the hotel’s walls. 21c Museum Hotel St. Louis dates to 1926 and was inducted into Historic Hotels of America in 2023. |
InterContinental New York Barclay (1926)
New York, New York
 | InterContinental New York Barclay defines romance through timeless elegance, discreet luxury, and a sense of place that feels unmistakably New York. Debuting in 1926, the hotel is woven into Manhattan’s cultural history, welcoming distinguished travelers and hosting meaningful occasions for nearly a century. Its storied past adds emotional depth to every proposal, allowing couples to begin their next chapter in a setting that feels both iconic and intimate. The Harold S. Vanderbilt Penthouse is the most romantic proposal location, offering privacy, refined design, and sweeping views of the Chrysler Building that create a cinematic and instantly recognizable backdrop. Golden hour and the evening are especially magical, as the skyline glows and the Chrysler Building lights up the moment. The InterContinental New York Barclay team is highly experienced in planning seamless and discreet proposals, from champagne tray reveals timed perfectly with the glowing skyline, to transforming a suite with candlelight, florals, music, and a handwritten note for an intimate turndown proposal. Customizable proposal and celebration experiences can include luxury accommodations, champagne, floral arrangements, romantic dining, curated in-room touches, live music, transportation, photography coordination, spa experiences for two, and personalized keepsakes. Dining at the InterContinental New York Barclay is ideal for special occasions, and private candlelit dinners can be arranged either in a suite or in an intimate hotel setting. One of the hotel’s most memorable love stories involved a couple who met near the Chrysler Building and made “Meet me at the Chrysler” their daily ritual. When he proposed, the Penthouse Suite, with its glowing skyline and private terrace, became the perfect extension of their story. Soft candlelight, roses, champagne, a private dinner, and a pianist created a moment that was understated, emotional, and unmistakably New York, reflecting the sense of place and history that make InterContinental New York Barclay such a meaningful setting for life’s most important milestones. InterContinental New York Barclay was inducted into Historic Hotels of America in 2025. |
The Fairmont Sonoma Mission Inn & Spa (1927)
Sonoma, California
 | The Fairmont Sonoma Mission Inn & Spa is a naturally romantic retreat, rooted in the land and its ancient geothermal springs that have drawn those seeking restoration and connection for centuries. Nestled in the heart of Sonoma Valley, the resort offers an atmosphere that feels intimate, timeless, and deeply meaningful. One of the most beloved proposal locations is the resort’s private gardens at golden hour, where manicured lawns, lush greenery, and soft evening light create a private wine country oasis. Indoors, a terrace or suite overlooking the gardens, glowing with candlelight and fresh florals, provides an equally enchanting setting for a quiet, personal moment. The dedicated team collaborates discreetly with each “asker,” arranging ring reveals during champagne toasts, elegant dessert presentations at Santé, or after private spa rituals enhanced with rose petals and live music. Bespoke engagement experiences may include luxurious accommodations, spa indulgences, private dining, champagne, florals, and personalized touches, such as a private wine blending session at a neighboring winery. For couples seeking something unforgettable, Spa Under the Stars offers a serene and intimate atmosphere, as the geothermal pools glow beneath the night sky, creating a magical backdrop for a proposal. Santé restaurant provides refined, seasonal cuisine for celebratory dinners, and couples can also arrange private candlelit meals in secluded gardens, on terraces, or in exclusive indoor venues, with curated wine pairings. Additional enhancements such as spa rituals, rose petal turndowns, in room champagne and caviar, live acoustic music, private poolside moments, and custom calligraphy notes ensure every proposal feels effortless, personal, and unforgettable. The Fairmont Sonoma Mission Inn & Spa dates to 1927 and was inducted into Historic Hotels of America in 2014. |
The Don CeSar (1928)
St. Pete Beach, Florida
 | Affectionately known as Florida’s iconic Pink Palace, The Don CeSar has been a symbol of romance, glamour, and celebration since opening in 1928, welcoming celebrities, dignitaries, and couples to its sugar white sands for nearly a century. Its blend of old world elegance and timeless coastal beauty creates a sense of occasion that elevates every proposal, especially at sunset on the beach, when the gulf glows in shades of pink and gold behind the hotel’s famous façade. Couples also love proposing on private oceanfront terraces or balconies, where the sound of the waves adds serenity, or inside Maritana restaurant, where refined ambiance and artful cuisine enhances an intimate, candlelit setting. The Don CeSar’s concierge and events teams excel at coordinating discreet, personalized proposal moments, from champagne toasts and custom desserts, to private beach setups with rose petals, ensuring perfect timing and seamless execution. Celebrations continue with elevated dining at Maritana, private dinners under the stars, couples spa rituals, in room champagne and floral arrangements, live acoustic music, sunset photography sessions, and gatherings in the hotel’s bars or lounges. For nearly a century, The Don CeSar has served as the backdrop for countless engagements, weddings, and anniversaries, with many couples returning, generation after generation, to celebrate life’s most meaningful milestones. The Don CeSar was inducted as a Charter Member of Historic Hotels of America in 1989. |
The Graylyn Estate (1932)
Winston-Salem, North Carolina
 Photo by Chelsea Renay | The Graylyn Estate is romantic by design, a place where European inspired architecture, intricate ironwork, and 55 acres of manicured grounds create the feeling of stepping into a fairytale. Since its earliest days as the Gray Family’s grand manor, the estate has welcomed guests seeking beauty, privacy, and a sense of timeless escape. That history, paired with gardens, courtyards, and storybook pathways, creates a setting where proposals feel deeply personal and rooted in place. Many couples are drawn to the historic bridge at sunset, where a 1930s stone span arches over the pond, and the surrounding greenery glows in the evening light. Others choose the Mews, a French style courtyard featuring a fountain that becomes especially romantic as the day softens into dusk, or the Persian Card Room, where candlelight reflects off vintage architectural walls that originated in Syria in the 17th and 18th centuries. The Graylyn Estate team coordinates discreet proposal touches, from private dinners and rose petal turndowns, to champagne reveals and personalized moments staged in hidden corners of the estate. The Romance Getaway Package adds to the celebration with early check in, late check out, champagne, chocolate covered strawberries, fresh roses, a keepsake print, and a chef curated breakfast for two, along with thoughtful amenities such as transportation to Reynolda Village and Mrs. Gray’s famous butterscotch cookies. Many couples return to The Graylyn Estate because of the memories that they have created here, from alumni who met at nearby Wake Forest University, to families who have celebrated weddings and anniversaries across generations. Some even reflect on the idea that The Graylyn Estate has quietly witnessed their story unfold long before the proposal itself. That sense of history, continuity, and full circle romance is the true magic of The Graylyn Estate. The Graylyn Estate dates to 1932 and was inducted into Historic Hotels of America in 2016. |
Royal Palms Resort and Spa (1948)
Phoenix, Arizona
 | Royal Palms Resort and Spa in Phoenix, Arizona, feels like a secluded Mediterranean villa where romance naturally unfolds, thanks to its origins as the 1920s winter home of Delos and Florence Cooke and its winding pathways, lush courtyards, ivy covered alcoves, and intimate hideaways. Couples proposing here gravitate toward Camelback Vista, a tucked away garden with a stone fireplace and soft lighting that creates a cozy, private atmosphere, or Alegria Garden, an intimate space framed by mature trees and an old world wooden door that leads to a built in stage perfect for unforgettable moments. Other picturesque spots such as the Reflecting Pool, Florence’s Alcove, Montavista Courtyard, and corners of T. Cook’s restaurant offer effortless backdrops that need little more than rose petals or candlelight. The resort’s private dining coordinator helps couples plan every detail, from musicians and photographers, to surprise family arrivals and celebratory dinners, and many guests enhance the experience with the Royal Romance package or a Via Cappello private dinner set in a hidden corner of the resort With a long history of hosting everything from elopements to grand weddings, Royal Palms Resort and Spa continues to inspire lifelong devotion, drawing couples who dream of celebrating their love in a place that feels timeless, intimate, and deeply personal. Royal Palms Resort and Spa dates to 1948 and was inducted into Historic Hotels of America in 2000. |
Surf & Sand Laguna Beach (1948)
Laguna Beach, California
 | Surf & Sand Laguna Beach is romantic by nature, set directly on the shoreline where the rhythm of the Pacific Ocean meets decades of coastal history. Since welcoming travelers in the mid 20th century, the resort has been a beloved retreat for artists, writers, and couples drawn to Laguna Beach’s creative spirit and timeless beauty. That legacy, paired with unobstructed ocean views, creates a setting where proposals feel deeply personal and rooted in place. The most romantic locations are the oceanfront terraces overlooking the Pacific at sunset, when the sky glows in soft pink and gold, or a private suite balcony where the sound of the waves creates an intimate and unforgettable moment. Splashes restaurant and the guest services team coordinate discreet ring deliveries, whether hidden in a custom chocolate shell, tucked inside a glass bottle with a handwritten note and placed along the shoreline, or set thoughtfully in the guestroom before a planned moment. Romance month packages in February add to the celebration, and Splashes offers an especially magical dining experience as the sky shifts to gold, pink, and lavender above the shoreline. Bespoke engagement experiences can include private beachfront or terrace dining, customized champagne and dessert pairings, rose petal turndown amenities, spa experiences for two, and personalized keepsakes. Many couples return to Surf & Sand because of meaningful memories, from first dates at Splashes to family staycations spent on the same stretch of sand. Some couples even reflect on the idea that they likely crossed paths here long before they met. For these couples, getting married at Surf & Sand is about honoring a shared history and a place that has quietly witnessed their lives evolve from childhood memories to adult love. That sense of full circle destiny is the true magic of the resort. Surf & Sand Laguna Beach dates to 1948 and was inducted into Historic Hotels of America in 2021. |
El Conquistador Resort (1962)
Fajardo, Puerto Rico
 | Set high above the Atlantic Ocean on a dramatic cliffside, El Conquistador Resort offers a romantic setting rooted in more than 50 years of Puerto Rican heritage, where generations of guests have celebrated love stories and meaningful milestones. Nearly every corner of the resort provides sweeping views of the sea and sky, giving couples countless intimate and personal places to propose, with Casitas Garden standing out as the most iconic location thanks to its lush greenery and breathtaking ocean backdrop. The resort’s groups and events team works discreetly with each “asker” to plan unforgettable moments, from illuminated “Marry Me?” displays overlooking the water, to surprise ring reveals during romantic dinners or quiet sunrise proposals by the pool. Couples can continue the celebration with fine dining, private Jacuzzis with ocean views, sunset catamaran cruises, spa experiences, private cabanas, breakfast in bed, or scenic strolls through the resort’s gardens and cliffside paths. Over the years, El Conquistador Resort has become a cherished backdrop for milestone anniversaries and love stories throughout the generations, with couples returning decades later to celebrate engagements, weddings, and family traditions that began on this timeless stretch of the island. El Conquistador Resort dates to 1962 and was inducted into Historic Hotels of America in 2021. |
To be considered for membership in Historic Hotels of America, a hotel must be at least 50 years old; designated by the U.S. Secretary of the Interior as a National Historic Landmark or be listed in or eligible for listing in the National Register of Historic Places; and must honor its historic authenticity, sense of place, and architectural integrity while providing guests with fine hospitality. Visit HistoricHotels.org to learn more, and sign up for the program’s newsletter to stay up to date on news and specials from Historic Hotels of America.
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