5* The Liberty

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.

Hyatt Regency is one of the easiest places to base yourself for a first trip to Boston. It sits in the Theatre District, a few minutes from Boston Common and Downtown Crossing, with the historic centre, waterfront and South End all straightforward to reach on foot or by subway. Rooms are contemporary and comfortably sized, while the sixth-floor leisure area includes something increasingly unusual in central Boston — a heated indoor swimming pool. There’s also a sauna and 24-hour fitness centre with Peloton bikes. Avenue One serves New England-inspired food throughout the day, with the Lobby Bar handling drinks later on. This is very much a practical full-service city hotel rather than somewhere you book for boutique atmosphere, but the central location makes exploring Boston unusually simple. GayMapper tip: a particularly useful choice in colder months when having an indoor pool and plenty of the city within walking distance starts to feel like quite a luxury.

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.

Harborside Inn is a characterful alternative to Boston’s big downtown chains. The hotel occupies a converted 19th-century mercantile building on State Street, with exposed brick, granite walls, high ceilings and oversized windows giving many of the rooms a genuine sense of history. Its location is excellent for sightseeing. Faneuil Hall, Quincy Market, the waterfront, North End and Freedom Trail are all close, and Aquarium subway station is practically outside. Rooms are fairly straightforward but comfortable, with large TVs, fridges and free Wi-Fi. Some Atrium rooms face the hotel’s internal lightwell, while Cabin rooms on the lower floor have no windows — worth knowing when choosing the cheapest rate. The former lounge is currently not serving food or drinks, so plan on eating out. GayMapper tip: a very handy choice if sightseeing location and price matter more than hotel facilities — just check which room type you’re booking if natural light is important to you.

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.

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.