4* Eurostars The Boxer

Sleeping in jail is considerably more appealing when the jail looks like this. The Liberty, a Luxury Collection Hotel, occupies the beautifully restored former Charles Street Jail, where the dramatic 90-foot rotunda and original ironwork have been incorporated into one of Boston’s most distinctive luxury hotels. The 298 rooms are thoroughly modern, but the public spaces make playful use of the building’s history. CLINK. occupies former cell areas, Alibi sits in what was once the jail’s drunk tank, while Scampo adds Italian-inspired dining. The enormous lobby also becomes something of a nightlife destination itself, with DJs, live jazz, fashion events and regular evening programming. The hotel sits at the foot of Beacon Hill beside the Charles River Esplanade and Charles/MGH subway station. GayMapper tip: choose The Liberty if you want a hotel with genuine wow factor — the building and social atmosphere make it feel much more memorable than a conventional five-star.

Hotel AKA Boston Common has changed considerably since its days as Kimpton Nine Zero. The newly transformed hotel now has a calmer, more residential feel, with contemporary Scandinavian-influenced rooms and a polished new look throughout. The location remains excellent. You’re on Tremont Street beside Boston Common, with Downtown Crossing, Beacon Hill, the State House and Freedom Trail all within minutes. Rooms range from smart standard categories to spacious suites and an impressive penthouse with panoramic skyline views. There’s also a 24-hour Technogym fitness centre, intimate a.bar cocktail lounge and The Bosworth restaurant, which mixes New England ingredients with Mediterranean influences. Despite the central address, the overall atmosphere is more grown-up and relaxed than many of Boston’s livelier downtown hotels. GayMapper tip: particularly good if you want sophisticated modern design and an exceptionally central location without the formality of a traditional grand hotel.

Staypineapple has one of the most useful locations on this list for LGBTQ+ travellers. It sits on Chandler Street in the South End, close to Club Café and other queer-friendly nightlife, while Back Bay, Newbury Street and Boston Common are all comfortably walkable. Rooms are compact but cheerful, with seriously comfortable bedding, walk-in showers and the playful pineapple touches that stop the hotel feeling too corporate. Downstairs, Trophy Room is a destination in its own right — a lively, inclusive neighbourhood restaurant and bar that draws plenty of locals as well as hotel guests. Weekend breakfast, cocktails and regular events give the place a much more social feel than the average small hotel. There isn’t a gym or pool, but for this location you may not miss either. GayMapper tip: one of the best Boston choices if you want to stay somewhere that actually feels connected to the local LGBTQ+ scene rather than simply being gay-friendly.

Moxy is a good fit if you like your hotel lively, informal and right in the middle of things. It sits on Tremont Street in the Theatre District, close to Boston Common and only a short walk from Jacques’ Cabaret and the South End. Rooms are compact — deliberately so — with a clean modern design and big windows in many categories. The idea is that you spend more time downstairs, where Bar Moxy combines reception, breakfast area, cocktail bar and social space in one energetic room. There’s also a 24-hour grab-and-go market and a well-equipped fitness centre, but no traditional room service or full-service restaurant. The location is particularly useful for evenings out because both the Theatre District and several LGBTQ+ venues are reachable on foot. GayMapper tip: best for sociable travellers who don’t need a huge bedroom and would rather have a fun lobby, central location and plenty happening around them.

Hotel Commonwealth is the standout option if Fenway rather than Downtown is where you want to be. It sits directly in Kenmore Square, with Fenway Park almost in the back garden and the House of Blues, MGM Music Hall and Boston University all close by. The 245 rooms are noticeably spacious by Boston standards, with contemporary interiors and plenty of higher categories offering views towards Fenway Park or the famous Citgo sign. Food and drink have changed considerably in recent years. Blue Ribbon Sushi now sits at the hotel entrance, while Row 34 brings excellent New England seafood to the other side of the lobby. There’s also a 24-hour fitness centre and in-room dining. Kenmore subway station is right beside the hotel, so Downtown and the South End remain easy to reach even though you’re staying farther west. GayMapper tip: particularly good for baseball fans, concert trips or anyone who prefers the energy of Fenway and Kenmore Square to the historic downtown core.

Eurostars The Boxer occupies one of Boston’s more unusual hotel buildings: a narrow, triangular Flatiron-style landmark dating from 1904 in the historic West End. The 80 rooms mix industrial details with warmer New England touches, and the small scale gives the hotel more personality than the larger properties around nearby North Station. There’s free Wi-Fi, coffee machines and a 24-hour gym, with continental à la carte breakfast available each morning. TD Garden is only a couple of minutes away, making this an especially useful choice for concerts, Celtics or Bruins games. Beacon Hill, the North End, Freedom Trail and Faneuil Hall are also comfortably walkable. There’s no pool and the hotel doesn’t have its own parking, although discounted parking is available nearby. GayMapper tip: a good option if you want a distinctive little hotel and plan to explore the historic northern side of central Boston on foot.