Boston Gay and Lesbian Vacations



Your gay Boston vacation

Steeped in American history and characterized by an almost British reserve among its populace, Boston is a unique city in many ways. It seems there's a university everywhere you turn in Boston, and a liberal and youthful vibe wafts through the city -- despite its New England stuffiness. This is progressive Massachusetts after all, the first state in the nation where same-sex marriage was legalized.

Featured Hotels

LGBT-welcoming Boston hotels

From $148

W Atlanta - Downtown

4 stars
4.3 / 5 55 reviews

Atlanta, Georgia

The W Atlanta – Downtown hotel bills itself as an urban oasis in the heart of downtown Atlanta. The hotel is stylishly designed with a mix of light and colors that seems to take just a little of the heat out of Hot-Lanta. With vibrant restaurants serving anything from snacks to American and French cuisine to the outdoor... More

From $269

The Westin Copley Place, Boston

4 stars
4.3 / 5 122 reviews

Boston, Massachusetts

The Westin Copley Place Boston Hotel provides its guests with a relaxing experience in the midst of one of America's most exciting cities. It is situated right next to Copley Place-a premier shopping destination-and within walking distance of many of Boston's most popular attractions. The views of the Charles River and... More

From $260

Nine Zero, a Kimpton Hotel

4 stars
4.5 / 5 102 reviews

Boston, Massachusetts

Save 10% on your stay

The Nine Zero is a superior boutique hotel in Boston that offers renowned hospitality from the Kimpton Company. The hotel's exterior is constructed from traditional red brick, and the rooms feature stylish yet comfortable design elements. Guests of the Nine Zero will appreciate its convenient location in the center of... More

From $233

Onyx, a Kimpton Hotel

4 stars
4.2 / 5 80 reviews

Boston, Massachusetts

Save 10% on your stay

Onyx Hotel, a AAA four diamond, four-star boutique hotel sits on a charming side street in the heart of downtown Boston near many top sites like Faneuil Hall, TD Garden and the Freedom Trail. An eco-friendly, pet-friendly property, the Onyx offers upscale sophistication throughout the hotel. Begin the day with... More

From $279

Copley Square Hotel

4 stars
4.1 / 5 73 reviews

Boston, Massachusetts

Since opening its doors in 1891, the Copley Square Hotel in Boston has offered upscale lodging that embodies true New England hospitality. Original extrusions of Greek columns around windows, and decorative arches above the entrance still stand. With a rich heritage and AAA 4-Diamond rating, this hotel lives up to some... More

From $307

W Boston

4 stars
4.4 / 5 67 reviews

Boston, Massachusetts

Featuring modern and sophisticated décor in its public spaces that perfectly compliment the beautiful glass façade of the building, W Boston is located in the heart of the theater district in Boston's exclusive Midtown area. The hotel's location offers easy access to dining, shopping, and entertainment venues, and is... More

From $211

Marlowe, a Kimpton Hotel

4 stars
4.5 / 5 128 reviews

Cambridge, Massachusetts

The Hotel Marlowe is a AAA four diamond-rated boutique property emanating elegance and vibrancy with eclectic style throughout the space. Overlooking the Charles River, the hotel offers easy access to MIT and Harvard, as well as some of Boston's best attractions and upscale neighborhoods. The Green Seal-certified,... More

From $247

Boston Marriott Copley Place

4 stars
4.2 / 5 199 reviews

Boston, Massachusetts

Boston Marriott Copley Place will introduce you to the pulse of Beantown from day one, with its indoor entry to both the Copley Place Mall and the Prudential Center. Abstract art stands out in the bright mezzanine lobby with its triangular skylight, while views of the urban skyline and nearby Charles River are never far... More

From $349

Boston Marriott Long Wharf

4 stars
4.3 / 5 87 reviews

Boston, Massachusetts

Rate includes breakfast

Though only built in 1982, Boston Marriott Long Wharf hotel sits within an integral part of Boston's history and the 17th century focal point of Boston's sea trade. Emulating the warehouse-feel of the old city, the diamond structure is matched inside with the geometric lighting and wall design of the Waterline Dining... More

From $244

Courtyard Boston Downtown

3 stars
3.6 / 5 69 reviews

Boston, Massachusetts

Rate includes breakfast

A restored historic 1925 building houses this Back Bay hotel in the heart of Boston's theater district near convention centers and the city's top attractions, making it perfectly suited for business and leisure travelers. The AAA three diamond-rated hotel features 315 European-style guest rooms with 300 thread-count... More

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Best in Stay

LGBT Best in Stay Boston hotels

From $297

Ames Boston Hotel

4 stars
4.3 / 5 60 reviews

Boston, Massachusetts

History buffs appreciate both the location and original architecture of the AMES in the Byzantine-Romanesque Ames building. Built in 1893 as headquarters for the Ames farm equipment empire, the boutique hotel showcases mosaic tile ceilings, ornate staircases, carved marble fireplaces and dramatic arched windows. Designer... More

From $423

Boston Harbor Hotel

5 stars
4.6 / 5 41 reviews

Boston, Massachusetts

Save 10% on your stay

The Boston Harbor Hotel continues to earn accolades by pampering guests with fine rooms, fine dining, and a standout waterfront location. The architectural grandeur of the hotel's stunning arched entryway opens up to a breathtaking view of the private marina, and its rooftop terrace towers 16 stories over the Financial... More

From $293

Lenox Hotel

4 stars
4.7 / 5 243 reviews

Boston, Massachusetts

The Lenox Hotel is designated as one of the Historic Hotels of America, as well as being an outstanding' green' venue with sustainability practices and recycling initiatives. Since 1900, luxurious European-themed accommodations have hosted rich and famous guests, including jazz legend Duke Ellington. Classic elegance... More

From $476

Four Seasons Hotel Boston

5 stars
4.4 / 5 5 reviews

Boston, Massachusetts

Save 25% on your stay

This hotel is located near many of Boston's historical and cultural attractions, the business and financial districts, and the beautiful Beacon Hill area. The Four Seasons Boston offers guests elegant, old-world hospitality combined with state-of-the-art facilities and amenities. The hotel offers guests a full array of... More

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Departure Arrival Travel dates Round-trip
San Francisco Boston Tue, Sep 1 - Wed, Sep 2 $352
Chicago Boston Tue, Sep 1 - Wed, Sep 23 $147
Los Angeles Boston Mon, Aug 31 - Tue, Sep 1 $336
Washington DC Boston Tue, Aug 18 - Wed, Aug 26 $161
Seattle Boston Tue, Aug 18 - Thu, Aug 27 $303
Raleigh Boston Mon, Jul 13 - Mon, Jul 20 Check rates
Minneapolis Boston Wed, Sep 2 - Wed, Sep 9 $232
Atlanta Boston Thu, Sep 3 - Sat, Sep 12 $220
London Boston Mon, Aug 31 - Mon, Sep 21 $686
New York Boston Mon, Aug 3 - Sun, Aug 9 $193
Charlotte Boston Tue, Aug 11 - Tue, Aug 25 $191
Phoenix Boston Tue, Aug 18 - Tue, Aug 25 $304
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Why book on Orbitz?

  • Miss Richfield 1981 says it best in this video—not all travel sites are created equal. When you book on Orbitz, your travel dollars work harder. Here’s why:  

    • We’re the ONLY leading travel agency with a perfect Corporate Equality Index Score from the Human Rights Campaign, with two GLAAD Media awards to boot.
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    • We feature the top gay-friendly accommodations, including Best in Stay hotels and gay resorts.
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  • The Boston gayborhoods

    The South End was the traditional gay neighborhood that the local queers gentrified, but now many straight families reside there cheek-to-jowl with the gays. Funky Jamaica Plain, south of downtown, has a pronounced lesbian population as does the neighborhood of Roslindale.

    Around town

    Other general neighborhoods worth exploring are stately Back Bay; historic Beacon Hill, with its cobblestones and original gas lamps; busy Chinatown, which has been featured in many movies; and the North End, Boston's "Little Italy" although locals never call it that. And shopaholics will want to spend time on Newbury Street in Back Bay, filled with the city's best boutique shopping.

    Seeing Boston's sights

    For pure sightseeing, Boston offers up a smorgasbord for the history buff: Follow three-mile Freedom Trail to visit the Paul Revere House and the Old North. Or trace the Black Heritage Trail, a 20-block walk starting at the African Meeting House, the oldest black American church building still standing.

    LGBT events

    Pride happens in June, the food festival/AIDS benefit Taste of the South End in March. And don't forget the summer "gay beach" area on the Esplanade along the Charles River between Dartmouth and Gloucester, where guys tan in Speedos! The huge fireworks displays over the area pop off on the Fourth of July.

  • Keep your eyes peeled for plaques

    Boston excels at showcasing its history, and there seems to be a plaque on every other building. It's like a free tour and more interesting than any textbook.

    Watch out for the school calendar

    Boston hotel rooms can be hard to come by during graduation in early summer and orientation in late summer. Mid-summer can be a great time to visit, thanks to fewer crowds and glorious weather. But once fall starts, the leaf peepers use Boston as a base, bringing up hotel rates.

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