Top 25 Historic Hotels for a Romantic Proposal

Historic Hotels of America

Create Your Love Story for the Ages at a Historic Hotel

Historic Hotels of America^® turns romantic celebrations into life’s most cherished moments. With over 300 historic hotels, inns, and resorts, Historic Hotels of America is home to the largest collection of the most romantic hotels. From breathtaking backdrops to champagne and chocolates, our historic hotels set the stage for romance. From having the proposal delivered by a Falcon or a Torch-lighting runner or served inside a special dessert or cocktail, each historic hotel offers a unique and memorable way to make the romantic proposal unforgettable. Read about our top places to propose for 2019.

The Buccaneer (1653)
St. Croix, U.S. Virgin Islands

The Buccaneer is the Caribbean’s oldest family-run resort and is celebrating its 70th year of welcoming guests and sharing its history and hospitality in 2018. With roots dating back to 1653, The Buccaneer has evolved from an 11 room inn to a destination resort that sits on 340 lush tropical acres. Pop the question while overlooking the Caribbean Sea on beautiful Mermaid Beach or over a candlelight dinner just for two in the intimate 16th century Sugar Mill, the resort’s highest and most historic point. Afterwards, couples can look forward to the start of their new lives together while walking hand-in-hand along one of the most beautiful beaches in the world. The resort’s exclusive Romance Package allows sweethearts to experience privacy and romance. The package includes private round-trip airport transfers, one category room upgrade with guaranteed king bedded room, welcome Prosecco and fine chocolates, a 50-minute in room couples massage, a private sunset sail cruise, private dinner in the historic Sugar Mill, and more.

The Omni Homestead Resort (1766)
Hot Springs, Virginia

This historic hotel has a very unique way for someone to pop the question! Guests of The Omni Homestead Resort can participate in a field sports tradition that stretches back nearly 4,000 years, falconry. One couple had the unique experience of having a hawk carry the special message of a proposal. After the bride said “yes,” the couple took the hawk hunting in the woods, then ended the day with a visit to the hot springs, restaurants, and hiking trails at the resort.

Omni La Mansion del Rio (1852)
San Antonio, Texas

Blending Spanish colonial architecture and European style, the four-diamond Omni La Mansion del Rio surrounds guests with the romance, grace and charm of a grand hacienda. Nestled along the historic River Walk among the banks of the Paseo del Rio, Omni La Mansion del Rio creates a romantic, tranquil getaway all while in the heart of downtown San Antonio. The centrally located courtyard at the Omni La Mansión del Rio Hotel transports guests away from the hustle and bustle of downtown San Antonio and into an intimate and romantic garden setting and is a popular location for couples to get engaged. If couples choose to enhance the engagement experience, the concierge can help by including our signature candlelight set up with both pillar and votive candles which truly enhance the natural beauty of this elegant outdoor space. The Luxury & Love Package includes luxurious accommodations, concierge pre-call to assist with special romantic requests, two mini bottles of Moet & Chandon Rosé Champagne with chocolate covered strawberries, “romantic” turndown with robes, music and lighting, and late check-out of 1:00 PM.

Omni Parker House (1855)
Boston, Massachusetts

Parker’s Restaurant holds significance for John F. Kennedy, as Table 40 is where he proposed to Jacqueline Bouvier. The hotel continues to have couples get engaged at the same spot due to its heritage. Omni Parker House has customizable package that will really set the stage to sweep your sweetheart off their feet with champagne, chocolate covered strawberries, and more.

Mohonk Mountain House (1869)
New Paltz, New York

Surrounded by 40,000 acres of pristine wilderness, set on a glacial lake, overlooking the majestic Catskill Mountains, this Victorian castle resort is the perfect setting to immerse your special someone in the beauty and peace of nature. With an award-winning spa, gourmet cuisine, handcrafted cocktails, and countless recreational offerings, Mohonk Mountain House is the perfect place for a romantic getaway. Sky Top Tower is one of the most popular spots at Mohonk Mountain House for a proposal. At an elevation of 1542 feet, Sky Top Tower overlooks the iconic resort and gives a sweeping view of the Shawangunk Ridge and the valley below. After climbing the 100 steps to the top, visitors love this picturesque, inspirational location for popping the question. It makes for great photos and even better memories. The Special Occasion Package is often requested for engagements, honeymoons, anniversaries, birthdays, etc. Complete with fresh flowers, a bottle of wine, turndown, and in-room breakfast along with three daily meals and access to most resort activities, the Special Occasion Package is ideal for couples celebrating an engagement.

The Peabody Memphis (1869)
Memphis, Tennessee

A proposal is made all the more special at The Peabody due to the beautiful backdrops, elegance and rich history of the hotel. There are two very unique and special places in this historic hotel that couples often get engaged, The Peabody Rooftop and in the hotel’s fine dining restaurant Chez Philippe. Proposals have also taken place in front of the duck fountain, at the Christmas tree during the holidays, and from the stage during a Peabody Rooftop Party. The Peabody offers two romantic packages, Be Mine 1 which includes champagne, roses, tuxedo strawberries, rooftop/skyway venue, tuxedo-clad banquet captain, and valet parking. The Be Mine 2 package includes Chez Philippe five course dinner for two, champagne, special engagement dessert and/or ring box, and valet parking.

Palmer House®, a Hilton Hotel (1871)
Chicago, Illinois

This historic hotel has celebrated over 140 years and 9,000 weddings. The Palmer House is a grand display of romance as it began as a wedding present from Potter Palmer to his true love Bertha Honore Palmer. The Mezzanine overlooking the 21 awe inspiring Lobby frescos by French painter Louis Pierre Rigal is the a sought after location to pop the question. For the chocolate lover, delivering the ring looped through the ribbon atop the brownie which originated in the Palmer House pastry kitchen in 1873 is a creative and fun way for some couples to get engaged.

Wentworth by the Sea (1874)
New Castle, New Hampshire

Wentworth By the Sea Hotel & Spa has Victorian "wedding cake" architecture and 21st century luxury (including full service spa) that makes the resort’s storied history a part of the couples legacy. Wentworth By the Sea is all about customizing the experience to each guest, but there's a whole menu of amenities to be delivered to the fiancée if the prospective bride or groom needs suggestions. There are a host of romantic spots on site to pop the question including the gazebo in the garden and fireside dinner in SALT, the hotel’s main restaurant. The Room to Rendezvous Romance Package is popular with couples. This package includes two night stay, dinner for two at SALT Kitchen and Bar, breakfast buffet for two, two 50 minute massages, champagne, turndown service and late check out.

Wentworth Mansion (1886)
Charleston, South Carolina

The Wentworth Mansion is located in the heart of historic downtown Charleston just steps away from some of the most romantic experiences in the south including the Charleston Battery, Rainbow Row, and private carriage rides for two. The Wentworth Mansion was built as a private residence by Francis Silas Rogers for his wife and family of thirteen children giving the hotel a feeling of warmth and romance. Stepping up to the rooftop cupola and enjoying views of the city with a glass of champagne is the perfect way for a couple to toast to their engagement. At Circa 1886 Restaurant, the restaurant on site, the staff has been known to hide the ring in the dessert or remove a silver dome to reveal the ring to the bride-to-be. The Over the Top Package is popular among couples getting engaged, and includes four memorable excursions to immerse yourself in Charleston’s rich history and Southern culture. Embark on a one hour private carriage ride of downtown Charleston, sip champagne while viewing Charleston’s breathtaking scenery with a 30 minute helicopter ride during the day or at sunset, indulge in a five course dinner featuring the chef’s tasting menu paired with wines at Circa 1886 Restaurant and step back in time with a private 90 minute Connoisseur Tour and Madeira Tasting at the historic 18th century Drayton Hall Plantation.

Grand Hotel (1887)
Mackinac Island, Michigan

Grand Hotel, America's Summer Place is the perfect romantic location for any couple looking for a romantic getaway. Owned by the Musser family for three generations the first class service and staff of the hotel make it for an unforgettable experience. The views from the Front Porch and many other places at the hotel are unlike any other. Located on an island without cars where the preferred mode of transportation is a horse-drawn carriage provides a magical experience for everyone. Woods Restaurant located in the interior of Mackinac is very romantic and a perfect dining experience for someone who is getting engaged or looking for a romantic evening. It starts with a 30 minute horse drawn carriage ride to Woods Restaurant which takes you through parts of Mackinac Island not seen by many. The interior of the restaurant is dimly lit with a rustic feel. There is a fireplace to help with the ambiance and a piano player. The Honeymoon/Anniversary Package is perfect for couples getting engaged at Grand Hotel. The package includes accommodations (three-night stay), full breakfast and dinner daily, fresh-cut flower arrangement, champagne basket, Grand Hotel fudge, afternoon tea, one hour carriage tour, and a 10% discount on any future Honeymoon/Anniversary packages booked.

The Pfister Hotel (1893)
Milwaukee, Wisconsin

For 125 years, The Pfister Hotel has been an icon of prestige in Milwaukee, celebrating countless engagements, weddings and anniversaries with guests from all over the world. The timeless elegance and impeccable style of architecture and design is unlike any place in the city, offering guests the opportunity for a truly unique experience. This enchanting hotel is a fantastic location to create an unforgettable engagement experience, just like a personalized fairytale. The incredible Pfister associates, dedicated to the highest level of service, will go above and beyond to make every couple feel like royalty. At Blu, the hotel’s bar and lounge located on the 23rd floor, couples can take in panoramic views of the Milwaukee skyline and Lake Michigan. With its relaxing ambiance of low lighting and lounge music, this intimate space is the perfect place for the most memorable, breathtaking proposal of your life. The Pfister Hotel offers a variety of romantic packages to help celebrate the unforgettable engagement. The Romantic Retreat Package offers couples the opportunity to make the proposal a truly unforgettable memory. This package includes chocolate truffles and champagne; a $50 credit to be used in the Pfister Café or the lobby lounge; and overnight self-parking.

West Baden Springs Hotel (1902)
West Baden, Indiana

The majesty of the atrium sets the stage for romance at this historic hotel. Couples can round out the experience of this romantic and historic hotel with a massage, horse-drawn carriage ride and a wine-tasting experience under the dome before retiring to their guestroom with a balcony overlooking the atrium. It’s the personalized service at this hotel that makes special occasions so popular. The Concierge has been behind the scenes on for surprise engagements at the hotel. For a few couples who asked for her help, the Concierge guided them to the prime spots to pop the question and got a photographer in on the plan to capture the magic moment. The Lovers Getaway Package is a great way to celebrate an engagement. Reserve a two night stay at this historic hotel and prepare to be pampered. When arriving, guests will find chocolates, a bottle of champagne and two logo glasses waiting. This package also includes a $100 dining credit at any of the fine dining restaurants on site. Start the day on an easy note by taking advantage of the $50 breakfast credit, and indulge in something special with a $300 spa credit at one of the hotel’s world-class spa facilities.

The Redbury New York (1903)
New York, New York

The Redbury New York is one of the best historic hotels for the Most Romantic Proposal with rooms inspired by the glamour of the 1920s, fantastic Roman Italian cuisine from Danny Meyer’s Union Square Hospitality Group, and a central location in the heart of New York, allowing for a once-in-a-lifetime experience in an unforgettable city. The hotel showcases evocative design elements, the intimacy of a plush pied-a-terre, romantic rouge accents, low lighting and a signature scent including nodes of wild honey, warm butter and vanilla, black tea, diffused throughout. This historic hotel has a special “engagement expert” (ie: the concierge) to help create the ultimate New York proposal, with an entire day planned from a hair/makeup, tickets to a show or museum (tailored to the couple’s interests), dinner at Marta, etc. the Redbury has offered guests to set up a proposal in the hotel’s ballroom with connected ivy-covered, romantically lit outdoor terrace with petals on the floor and a petal sign that says will you marry me. All set up with small tealights. Start your fairytale at The Redbury.

The Ostesaga Hotel and Cooper Inn (1907)
Cooperstown, New York

Every historic hotel is unique in its offerings, location and architecture for unique engagements, but with Lake Otsego as its backdrop, The Otesaga provides the most majestic and enchanting location for a romantic engagement. Known as ‘Glimmerglass’ in James Fenimore Cooper’s Leatherstocking Tales including The Deerslayer and The Pioneer, Lake Otsego is rich in history and its views are truly spectacular. A popular site to pop the question is on the back lawn of the resort, overlooking the lake and surrounded by century old Oak trees. The lake dock, with its quaint stillness and breathtaking views of the lake is another admired area to ask the question. There also those who rather be on the lake, in an old-fashioned boat with the resort as backdrop, and there are some who prefer to be on a horse drawn carriage pulling up to the resort’s front portico. The Baseball Hall of Fame, just minutes from the resort as well as the Doubleday Field are other great venues that are popular, especially with baseball fans. If the engagement is baseball themed, the hotel can offer a baseball base for the ring presentation or wrap the ring around a baseball. The Otesaga has also provided the assistance of dogs to deliver the ring.

Amway Grand Plaza Hotel (1913)
Grand Rapids, Michigan

Amway Grand Plaza Hotel is a landmark hotel in Grand Rapids and has also been a landmark for love and relationships for decades. Featuring crystal chandeliers, the signature golden starburst and grand fountain, the Pantlind lobby provides the perfect backdrop to create a unique and memorable proposal experience. This historic hotel offers offer two packages perfect for any couple celebrating a recent engagement. The first is the Celebration Package which includes a bottle of complementary wine or champagne and breakfast in the morning. The second is the and Salon package which is perfect for the couple looking to escape to the Amway Grand Plaza for a romantic getaway and to rejuvenate both body and spirit. This package includes a 50-minute couples massage, $50 food and beverage credit and complimentary valet or self-parking.

OHEKA CASTLE (1919)
Huntington, New York

OHEKA CASTLE's elegant and grand French Chateau-style estate and formal gardens offer the ultimate in European ambience right here in America and are the perfect backdrop for a memorable proposal. The hotel offers a special Marriage Proposal Package that includes dinner for two and a romantic turndown complete with champagne, chocolate covered strawberries and a rose petal turndown.

The Drake Hotel (1920)
Chicago, Illinois

A part of Real Chicago History, guests can expect truly authentic experiences. The Gold Coast Room is sought after by numerous brides to be as the “place” to be wed. Its massive elegance will take your breath away and the floor to ceiling windows showcasing stunning views of Lake Michigan will draw you in. The Drake’s catering professionals are esteemed for providing some of the most impressive celebrations transforming romantic fairytales into reality in an already opulent and historic hotel. The Unforgettable & All You Need Is Love Package features candlelit three course dinner for two served with champagne in a customizable setting and photographers to capture the moment.

Historic Hotel Bethlehem (1922)
Bethlehem, Pennsylvania

This historic hotel is known as the Christmas hotel in Christmas city, one of the most popular times to get engaged is during the holiday season. From Thanksgiving up until Christmas day, there is typically about one engagement per week. The most popular place to get engaged is in the lobby in front of the 16 foot Christmas tree. The second most popular location for proposals is 1741 on the Terrace, the elegant dining room of the hotel. With its breathtaking views of the historic district, guests dine for dinner and find a unique way to propose.

La Fonda (1922)
Santa Fe, New Mexico

La Fonda is located on a historic Plaza, where weddings and engagements have taken place for centuries. While the hotel bustles by day, there is an Old World intimacy about the hotel, especially with its wood burning Kiva fireplaces, Spanish Revival decor and a restaurant that is filled with twinkling lights by night, and sits on a former outdoor patio. This historic hotel offers couples a customized package to make their proposal extra special and can arrange for private dinners overlooking a beautiful cathedral and the mountains of Santa Fe. In six years, the Concierge estimates they have helped plan over 50 engagements at La Fonda.

The Brown Hotel (1923)
Louisville, Kentucky

Since 1923, the historic Brown Hotel in downtown Louisville has provided the perfect backdrop for weddings, romantic dinners and celebratory events. Whether it is in the privacy of a guestroom, on top of the world on the Roof Top Garden or in the hands of the chefs in the English Grill, the Brown Hotel has been celebrating romance for nearly a century. Each romance is special and unique as the spirit and passion that built this very building. Stepping into the hotel feels like stepping back in time with its elegant chandeliers and majestic décor. Popular engagement locations at this hotel include the 16th floor rooftop garden with the finest views in the city, the Crystal Ballroom with its hand-painted ceiling surrounded by chandeliers, The English Grill, the excitement of the Chef’s Table or our Muhammad Ali Suite, among many places in the hotel, guests will feel like a celebrity.

Hotel Constance Pasadena (1926)
Pasadena, California

Pasadena California’s historic Hotel Constance could be called the perfect spot to pop the question. Built in 1926, the hotel has nearly a century of history as romantic getaway. The hotel’s BluRoom Lounge perfectly blends modern design with the building’s classic architecture and makes a perfect backdrop for asking that very special question. Being the home of the annual Rose Parade, several museums and nationally recognized cultural attractions, Pasadena itself has dozens of romantic spots for couples to enjoy, or to get engaged.

Omni San Francisco (1926)
San Francisco, California

Located in the heart of one of the world’s most romantic cities, Omni San Francisco offers the atmosphere to make an engagement picture perfect. There are a variety of locations at the hotel that are perfect for popping the question. The most sought after location is the historic grand lobby underneath the Austrian chandelier. Omni San Francisco can deliver an engagement ring in a number of fun and innovative ways including placement of the engagement ring in a champagne flute, brought to the guestroom by room service, or arranged to be handed over by a cable car driver.

The Royal Hawaiian, A Luxury Collection Resort (1927)
Honolulu, Hawaii

From its opening in 1927, The Royal Hawaiian has been recognized as an icon of luxury and romance. The hotel’s soaring pink turrets have lured couples from around the globe who come to discover the expansive beach at sunset, to share intimate moments in lush and legendary gardens, and to immerse in timeless beauty. Just steps from the beach, with a view of Diamond Head’s picturesque profile and directly facing the shoreline of Waikiki, the hotel provides the perfect place to pop the question.

The Don CeSar (1928)
St. Pete Beach, Florida

The Don CeSar is built in a Mediterranean and Moorish style architecture, surrounded by the turquoise gulf waters and pristine white sand beaches. 90 years ago this amazing architectural icon was built based on passion. The Don CeSar is the result of a young couple’s love that was never given the opportunity to flourish. Today it stands as a shrine to romance and commitment, and heirloom for everyone to share. The beautiful landscaped courtyard and grand staircase is a wonderful spot for a couple to start their life together. The hotel has assisted guests with proposals- having the beloved pet bring in the ring, placing the ring in gourmet culinary offerings, or even having it available hundreds of feet up on a parasailing excursion. The Don CeSar Romance Package includes champagne and strawberries, breakfast in bed, luxurious accommodations, as well as a full suite of included resort amenities.

The Renwick Hotel New York City, Curio Collection by Hilton (1928)
New York, New York

The hotel offers special romantic amenities to couples including a champagne toast, rose petal turn down or special in-room dining with romantic candlelit dinner catered by Bedford & Co. The Renwick Suite with a balcony overlooking New York City is a popular location for engagements. The Renwick also presents guests with private dining options and a special aphrodisiac dining menu and wine pairings. Chef John DeLucie has been known to deliver the ring or can put one in one of the menu items or cocktails. The love affair Zelda and F. Scott Fitzgerald is what inspired the popular Zelda cocktail at Bedford & Co.

InterContinental Chicago Magnificent Mile (1929)
Chicago, Illinois

This historic hotel is on Michigan Avenue, central to all the beauty of the city, the parks, the lights, in the historic district with amazing old world architecture of the Tribune Tower, London House and, Water Tower. With so many enchantingly beautiful spaces within the historic tower of the hotel it makes for a magical moment when someone decides to pop the question. The hotel is happy to work with couples to create the perfect engagement, offering a few packages that are celebration or romance specific. Michael Jordan's restaurant on site hosts a lot of engagements so the True Chicago Experience Package offers everything a guest need for a romantic weekend. Suite upgrade, a three course dinner for two at Michael Jordan’s, tickets and drink at Andy's Jazz Club, breakfast and parking are also included.

Hacienda Del Sol Guest Ranch Resort (1929)
Tucson, Arizona

This historic hotel offers customized experiences for all couples who want a romantic, unforgettable experience. The stunning backdrops and scenery are unparalleled, with expansive mountain views to the north, golf course and sunset views to the west and twinkling city lights to the south. Hacienda Del Sol provides assistance and creativity in any way the guests requests when it comes to proposals. This historic hotel has even had a ring delivered via donkey per one guests request.

The Wigmam (1929)
Litchfield Park, Arizona

One of Arizona’s first and most celebrated resorts, The Wigwam is filled with 100 years’ worth of history, Southwestern charm and authentic traditions, making it the perfect spot to start your own forever. Stretching across 440-acres of beautiful desert landscape, lined with 8,000 vibrant rose bushes, there are an abundance of locations to pop the big question; from charming courtyards surrounded by towering palm trees, to intimate terraces draped with twinkling lights, The Wigwam offers an experience truly like nothing else. After a beautiful beginning, couples can enjoy the historic resort, scenic views, fresh farm-to-table cuisine, relaxing spa treatments and an abundance of unique activities. The resort offers a special Stay & Snuggle Package, which invites couples to retreat to a relaxing, romantic stay. The package includes overnight accommodations in a luxurious suite with a fireplace, a welcome amenity with charcuterie and cheese board, bottle of wine, and breakfast for two in-room or at the Wigwam Bar.

The Hotel Hershey (1933)
Hershey, Pennsylvania

This historic hotel is located in Hershey, The Sweetest Place On Earth. Guests experience panoramic views of Hershey Gardens, Hershey Park, and the town of Hershey. The Hotel Hershey offers a variety of premier accommodations and amenities, and the fabulous mosaic fountain lobby is a beautiful experience with marble floors and beautiful woodwork. The lobby and the formal gardens at this hotel are the most popular locations for proposals and the hotel offers complimentary champagne, chocolate covered strawberries, and rose petal turndowns for newly engaged couples. The Hotel Hershey offers a special edible chocolate ring box, which features the engagement ring hidden inside chocolate nibs.

Morris Inn at Notre Dame (1952)
South Bend, Indiana

The Morris Inn is located in the center of the history-laden University of Notre Dame. Engagements on campus are special and memorable because of the tradition and history behind the University. Located just steps from the "Golden Dome", the Basilica of the Sacred Heart, and the Grotto of Our Lady of Lourdes, a weekend on campus is unforgettable. Create a memorable experience at the Morris Inn with our perfectly appointed traditional rooms, or in one of our suites - some of which are fit with a cozy Japanese soaking tub.

Mauna Kea Beach Hotel (1965)
Kohala Coast, Hawaii

The magical timelessness, laidback luxury, and fiery sunsets make his hotel is one of Hawaii’s most romantic and sought after destinations. Many choose the soft sands of Kauna’oa Bay at sunset for this life changing moment. The hotel offers two special locations for private dining including the exclusive vista deck and third hole tee on the Mauna Kea golf course. The third hole tee is perched just above the water’s edge, torchlight and very private, making it the perfect location to pop the question. The Mauna Kea has had a delivery of the ring by a malo-clad evening touch lighter and by baking the ring in a special dessert. This beachside resort offers the Exactly Like Nothing Else package which includes a special Mauna Kea honey amenity, volcano helicopter tour, private tour of the Mauna Kea beehives, and nighttime mantra ray snorkel adventure, perfect for a romantic retreat.

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