8 Coolest Hotels in Boston from a Former Jail to Beantown Boutiques

New England-based writer Robert Isenberg covers the coolest hotels in Boston featuring the best that Beantown has to offer.

Years ago, I visited Boston under the best circumstances: My book had just been released, and I was invited to do a reading at a local university. With 35 colleges and a robust literary scene, Boston is an author’s dream. There are bookstores galore, artists and engineers on every sidewalk, and some of the greatest minds in the world living in a 10-mile radius.

The city is also a playful labyrinth of sights and historic landmarks, best explored on foot. I stayed in a hotel downtown, and within an hour I had walked through the Chinatown gate, past the historic Orpheum Theatre, across Boston Common, beneath the 200-year-old State House dome, and strolled across the magnificent stone arches of the Longfellow Bridge. The Charles River glistened beneath a late-afternoon sun. Joggers and cyclists flew down the asphalt. On either shore, Boston and Cambridge throbbed with activity.

Boston is a whip-smart and funky town, a rich chowder of Ivy League intellect and blue-collar roots. In Boston, I’ve seen some of my favorite theater productions, attended the most memorable readings, and enjoyed some of the most rambunctious nightlife in my many years of culture-seeking.

This offbeat personality is visible in the trendiest Boston hotels, which can be nearly as engaging as the city itself. Spend one good night among its frenetic, fast-talking natives, and you’ll see why Boston is known as “the Athens of America.”

The Flatiron of Boston


The moment you see The Boxer hotel, you may think to yourself: “Wait a minute–isn’t that the Flatiron Building?” With its arrowhead shape, curving front, and all-brick facade, The Boxer looks remarkably like its Manhattan cousin. The Boxer is set in the historic Bulfinch Triangle, which has undergone a great deal of development. While the exterior is largely unchanged, the interior is newly renovated with a slick, minimalist design.

Boxer rooms have a subdued color palette and functional decor, and much of the furniture has a simple, Scandinavian elegance. Some rooms come with playful bunkbeds, and the frontmost accommodations show off the building’s peculiar shape.

There’s no shortage of dining options in this part of town, but Finch Boston Restaurant, located on the first floor, serves up delicious entrees such as the Marinated Lamb Top and Duck Pot Pie. The brick walls and leather chairs make you feel like you’ve walked into the opening credits of “Cheers.”

Hotel The Boxer Boston

Boston, 1.3 miles to Back Bay
8.4 Very good (3300 reviews)
Excellent Cleanliness 8.9 / 10
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Bikeable Boston


In the summertime, Boston can be very bikeable, which is one reason the free bikes at Kimpton Nine Zero are such a cool perk. Kimpton’s “healthy travel” program provides bikes in locations all over the world, and the chance to borrow a bicycle (for free!) in a pricey city like Boston will help you explore the neighborhoods in a whole new way.

These surprising little touches are exactly what Kimpton is famous for: There’s a yoga mat in every room, there’s a nightly wine reception in the lobby, a complimentary shoe-shine, and free access to the Boston Sports Club. The aesthetic, with its leather hammocks, oddball paintings (crossed-out faces, a bulldog dressed in a regal cape), and vintage phones and lightbulbs, is like a steampunk art gallery. Finally, there’s the Better Sorts Social Club, a sumptuous bespoke cocktail bar that sculpts every last beverage and entree into a masterpiece. Small wonder that Kimpton is always top-rated in the city.

Kimpton Nine Zero Hotel

Top rated
Boston, 1.1 miles to Back Bay
9.0 Excellent (3607 reviews)
Excellent Location 9.5 / 10
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"Designed to be Cool"


From the roadhouse-style sign to the clusters of concert posters on the walls, every inch of The Verb Hotel looks designed to be cool. The colored glass of the windows come together like a Piet Mondrian painting, and the postmodern art and mod color scheme give each room a whimsical vibe. Verb designers got their inspiration from classic rock, and each room is outfitted with its own record player.

The gimmicky atmosphere is fun and worth embracing, but no matter how you feel about The Beatles and Stones, the central pool is a rare Boston treat. The Verb is also a baseball’s throw from the Green Monster and scores of other cultural institutions, and the dining and nightlife in Fenway-Kenmore show off Boston at its best. The Verb even has an engaging website and regularly updated blog covering everything from health and wellness to local cultural institutions.

The Verb Hotel

Top rated
Boston, 0.9 miles to Back Bay
8.7 Excellent (4336 reviews)
Excellent Service 9.3 / 10
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The Former Charles Street Jail


The most surprising lodging in Beantown is The Liberty, which occupies a former Charles Street Jail. The original stone building dates back to 1851, and it looks like a cross between a town hall and a medieval castle. Where 19th-century inmates once scuffled over heels of bread–and incarceration still took place until 1990–an unconventional hotel has sprung up. Brick walls and barred gates remain intact, but the old catwalks have been brilliantly converted into walkways and balconies. Even the heavy metal chandeliers bridge the gap between overcrowded dungeon and luxury escape.

Unlike the cells of yore, Liberty rooms are plush and comfy; the only hints of its past are found in the artwork, which shows keys, maps, and archival photographs. Liberty Hotel is a provocative place, embracing a very dark history, but it’s also conveniently located on the edge of downtown and a short walk from Lederman Park and Charles River.

The Liberty, A Luxury Collection Hotel, Boston

Top rated
Boston, 1 miles to Back Bay
8.9 Excellent (3916 reviews)
Excellent Cleanliness 9.1 / 10
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Patriotic Kitsch


If you’re familiar with the story of Paul Revere–and Boston’s epic colonial past–you’ll appreciate the many playful touches at the Revere Hotel: the abstract horse paintings, the replica cannon, the throw-pillows styled after the Betsy Ross flag, and the full-sized sculpture of Revere atop Brown Beauty. Patriotic imagery is everywhere, but it isn’t the usual kitsch. Here, Revere appears in clever and surprising ways, and a history buff can’t help but smile.

Revere also has a sprawling rooftop, and although summers are brief, warm-weather travelers can enjoy some of the best panoramas in the city, along with drinks at the Rooftop@Revere cocktail bar. There’s also an indoor heated pool, which is perhaps the most luxurious amenity to exist in New England. Finally, there’s the Lobby Bar, which is largely decorated with antique shovels and showcases Boston distilleries in all its signature cocktails.

Revere Hotel Boston Common

Top rated
Boston, 0.7 miles to Back Bay
8.8 Excellent (9017 reviews)
Excellent Location 9.2 / 10
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A Proud Victorian Building


On its surface, the Inn at Saint Botolph is a handsome brownstone, tucked into an old street between Huntington and Columbus Avenues. This is one of Boston’s loveliest neighborhoods, and the Inn looks right at home among blocks of stately row houses; even the sidewalks are paved with brick. For its Back Bay location and architecture alone, this proud Victorian building is worth a stay.

The Inn at Saint Botolph offers more than old-world charm. The suites are remarkably spacious, and all of them come with their own kitchenettes. The hotel offers surprising 21st-century touches, such as keyless entry, video intercoms, and an on-site fitness center. If a typical inn looks like it’s been decorated by someone’s grandmother, Saint Botolph is pretty spry: rooms are modern and comfortable, and the windows overlook some of the prettiest streets in New England.

The Inn at St Botolph

Top rated
Boston, 0.4 miles to Back Bay
8.7 Excellent (468 reviews)
Excellent Location 9.3 / 10
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Boston's Mashup of a Japanese Capsule Hotel


There aren’t any “rooms” at Yotel Boston; rather, you have to ask for a “cabin.” Like a mashup of Japanese capsule hotels and the inside of a Boeing 747, Yotel’s accommodations exude sleek efficiency. Cabins can be as tiny as 152 square feet, but they more than make up for it in comfort. Each unit has an adjustable smart bed, a gel memory foam mattress, keyless entry, adjustable mood lighting, and a heated bathroom towel rack.

While Yotel has been downplaying the term “micro-hotel,” the compact quarters encourage visitors to explore the city. You can also take advantage of the rooftop patio, which has become a destination unto itself. Yotel also has space-age amenities, such as self-check-in kiosks and YO2D2, a “resident robot” that affably roams the lounge and hallways. (Remember, MIT is close by.) Such idiosyncrasies aren’t for everybody, but you won’t find anything else like it in the whole region.

Yotel Boston

Boston, 1.7 miles to Back Bay
8.4 Very good (2265 reviews)
Excellent Cleanliness 9.2 / 10
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Catch A Summer Sunset


In a certain light, the glass-and-steel superstructure of the Envoy Hotel is a real stunner, especially when it reflects the Boston skyline in its spotless windows. Watching a summer sunset from the Rooftop Lookout is one of the best things Boston tourists can do for themselves; you’d be hard-pressed to find a more romantic view of the waterfront.

The Envoy is prime luxury, featuring local art, brightly designed rooms, and the wildly acclaimed Lookout restaurant, which serves such unusual delicacies as Yuca Gnocchi and Red Snapper in Banana Leaf. The Envoy also represents the shining future of Bostonian life. It stands in the Boston Waterfront Innovation District, a spectacular renewal project that recently transformed 1,000 acres of industrial decay into a work-play utopia. This district is brand-new, and there’s no better launchpad to the Innovation District than the Envoy. Staying at the seaport is pricey, but here you’ll find the trendiest and most exciting new developments in the Boston hospitality scene.

The Envoy, Autograph Collection

Top rated
Boston, 1.7 miles to Back Bay
8.7 Excellent (540 reviews)
Excellent Cleanliness 9.3 / 10
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Feature image courtesy of The Liberty