Boston is brimming with history, thanks to its 1600s roots that make it one of America’s oldest cities. This is evident in the intricate brick structures and lavishly large homes, which now often serve as Airbnbs. Each neighborhood is unique, with some being a serious step back in time. Boutique shopping, artisan eateries, lovely fall foliage and coastal access reside within the city, so there’s always something to do. Staying in an Airbnb is a fantastic way to sink into local culture and seriously awesome digs, and these are our favorite picks.
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"Chef"Kitch, 12 MintoPru Boston studio apartment
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Boston studio apartment

"Chef"Kitch, 12 MintoPru

Industrial rustic, the studio apartment fits a lot into a small space, which can accommodate two guests comfortably. Brick walls envelop a sleeping area, cozy living room and fully stocked kitchen—aesthetics feel consistent with Boston itself. But the real gem is the snug outdoor patio space, with lots of lush foliage and a bistro table for morning coffee sipping. Since the heart of Downtown is around 20 minutes away, the apartment is a wonderful accommodation in a great neighborhood, so one can still have some disconnect from the bustle. Bonus—a portion of your rate goes toward local charities.

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Sonder | Boston Common Living room with city view window
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Living room with city view window

Sonder | Boston Common

Airy, modern, spacious and with an oh-so-dreamy bay window facing toward bakeries, restaurants and other quaint shopping, four guests can comfortably lounge here. To get to the center of town, just take a short subway ride. But with delicious international cuisine and amazing cocktail bars blocks away, you may just stay nearby. This particular Airbnb host has been featured in The New York Times, The Wall Street Journal and Fast Company.

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Beacon Hill Next To Statehouse Colonial charm living room
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Colonial charm living room

Beacon Hill Next To Statehouse

This Airbnb is like if a farmhouse and a Boston apartment had a baby. The homey condo has a cute bathroom with subway tiles and a pedestal sink, while rich brown flooring flows through the rest of the space. French doors add an adorable touch, as does the small but adequate kitchen. The location is about perfect, within the revamped Colonial district of Beacon Hill—many original aesthetics like gas lamps and brick sidewalks complement the intriguing history. But the best part of the condo is the accessible roof deck, where you can see downtown, and many of the area’s most iconic landmarks.

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Historic JP Brownstone Historic Airbnb
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Historic Airbnb

Historic JP Brownstone

Anywhere with historic roots in Boston is likely going to be a win. You can almost see the atmosphere over 100 years ago in this striking Brownstone building that blends perfectly into Boston’s other old gems. At 1,200 square feet, the condominium is spacious and absolutely charming. A beautiful wood banister staircase, wood flooring, a bay window along with countless other windows to let light in and floor-to-ceiling brick fireplace creates a cozy atmosphere. Boston is easily accessible from this Jamaica Plain location, but you have the benefit of peace and quiet with plenty of trees and grassy play areas.

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360° Deck and Private Bath Rooftop deck
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Rooftop deck

360° Deck and Private Bath

While the kitchen and commons area of this chic abode is shared, the lovely brick-walled bedroom and luxurious sunlit bathroom are all yours. Much of downtown is basically within walking distance, with Restaurant Row, endless shopping and alluring art galleries overflowing the district. Public transit is easily accessible and available to take you to the outskirts. But if we had to pick one majorly awesome aspect of this Airbnb, it would undoubtedly have to be the foliage accented deck with panoramic city views and ample seating—a night out here could easily be a trip highlight.

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Back Bay Studio Apt Studio Airbnb Boston
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Studio Airbnb Boston

Back Bay Studio Apt

Snug and cozy, this small apartment is both modern and welcoming, plus there’s a stunning rain shower that truly belongs in a spa. Newbury Street, Prudential Center, Boston Public Library and the Charles River are within this brick sidewalk, gas lamp-lit neighborhood. Shopping and dining are right outside, even though the Airbnb is in a relatively peaceful neighborhood—its a wonderful mix. But you might enjoy cooking up your own gourmet meal in the newly renovated kitchen.

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Studio in the Heart of Beacon Hill Bright studio apartment
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Bright studio apartment

Studio in the Heart of Beacon Hill

Ice skate in the winter and enjoy vibrant public gardens in the spring and summer, at this simple yet suave mini apartment in Beacon Hill. Boston Common, various shops and Charles River Esplanade’s Hatch Shell, a concert venue, are all right there, in the adorable district with a definitive antique vibe. Two guests can spaciously dwell in the studio, which has a lovely kitchen, white brick walls and updated rustic decor.

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Park View in Downton Boston Funky and vibrant Boston Airbnb
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Funky and vibrant Boston Airbnb

Park View in Downton Boston

The decor is colorful and funky, and the views couldn’t be better at this downtown situated accommodation, which ranks nearly seamlessly on Airbnb. The cozy apartment has one bath, a bedroom, kitchen and eating area, and features everything you need for a short or extended stay. Being directly downtown has major perks, as you are right beside parks, eateries and even the subway station. If looking for something efficient, fun, proximal and that can host around four people, this is a solid pick.

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Sunny Private Studio Apartment Victorian Airbnb
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Victorian Airbnb

Sunny Private Studio Apartment

Want to stay in one of those iconic Victorian homes in Jamaica Plain, that most dream about just taking a peek inside of? This is your opportunity. A full apartment within the home offers ample privacy, and touches of antique aesthetics like a claw foot tub, wood flooring and thick statement trim throughout. All the little extras take the third-floor apartment to “gem” status, such as the private entrance through the garden, and the locally baked treats left especially for you in the kitchen. For the most part, chemical-free cleaning products are used to get everything sparkling.

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Victorian Charm Historic Airbnb exterior
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Historic Airbnb exterior

Victorian Charm

Another lovely Victorian home apartment, located in Central Square, features enriching aesthetic and decor to pay ode to the past. Whip up some groceries from Trader Joe’s (which the owners will even take you to) in your cozy kitchen, then enjoy eating on the private back porch. The spacious outdoor space is exceptionally lovely come fall. While the home appears to have kept older aesthetics, the heat, water and other systems are updated to modern standards. The home also houses a second unit if you’re bringing the whole family.

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