10 of the Best Airbnbs in Boston, Massachusetts

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Known as both “the Hub” (as locals would say) and “Beantown” (as locals would never say), Boston is the famed location of Paul Revere’s “Midnight Ride” and the historic Boston Tea Party.

Full of rich American history and good ol’ New England charm, Boston is truly the “City Shining on the Hill.”

If someone in Boston ask you if you want to grab some beeyah from the packie and chill in the pahlah of your three deckah, you may be a little confused. But if you’re scratching your head and wondering what that person means, don’t worry — it’s just the decidedly Bahston accident you’ll hear everywhere in the city. They’re asking if you want to grab some beer from the liquor store drink it in your three-story house’s parlor (or living room).

If you take a trip to the Massachusetts’s capital, be sure to brush up on your Boston English to keep up with the crowd. There’s even a dictionary for Boston slang.

While Paul Revere may have been known for shouting “the British are coming,” today, it’s mostly tourists coming to Boston, likely because there’s so much to do and see. So try to book one of these airbnbs in Boston as soon as possible, especially since the city gets quite busy in the spring and summer.

1. Mid-Century Modern Triple-Decker

triple decker airbnb boston — Photo: Airbnb

Why you should stay: Master Boston’s tradition of pre-gaming with a fully stocked pantry and bar.

Sleeps: 7
Minimum stay: 28 nights
Rates from: $172/night

Stay in one of the iconic “three-deckers” with this rental home just a few blocks from the Boston Public Garden. With a wrap-around breakfast bar and Cuisinart coffee machine, you won’t need to do a ‘Dunks run (Bostonians love their Dunkin Donuts coffee) when staying here.

There’s more than enough room for the whole family with three floors of mid-century modern decor and comfortable furnishings. And if you need some time out in the city, you’re only steps away from some of the most iconic attractions, including Newbury Street shopping and Boston Common.

As with many airbnbs in Boston as of the time of this writing, the minimum stay may get much shorter once COVID-related travel restrictions are loosened.

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2. Renovated Brownstone

brownstone airbnb boston — Photo: Airbnb

Why you should stay: Take a complimentary sail on the host’s 50-foot yacht (bring your boat shoes.)

Sleeps: 8
Minimum stay: 3 nights
Rates from: $343/night

Live as regal as you feel by staying in this renovated four-bedroom duplex. With antique Victorian pieces scattered throughout the home, you’ll be living like a king. And if people have learned anything from COVID stockpiling it’s that toilet paper can be a luxury; fortunately, this home is equipped with a bidet. If you schedule it with the host, she can arrange for you to take a quick sale around the harbor – her dad is the captain, after all.

The home is quite roomy at 2,000 square feet, which includes two bedrooms with ensuites, another bedroom for two, and a fourth “kids room” with bunks. With multiple fireplaces and high-end appliances, it’s one of the more luxurious airbnbs in Boston – you may find yourself longing for a posh life in the city by the time you leave.

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3. Secluded Garden Suite

Why you should stay: A cozy little apartment near public transportation and Boston Common.

Sleeps: 2
Minimum stay: 2 nights
Rates from: $220/night

This private garden-level apartment is the perfect place for a getaway for two. It’s open enough to not feel cramped, but cozy enough that you’ll have to snuggle up in the living room. It’s a great rental for Boston winters, since the home has in-floor heating throughout.

And if you enjoy a good debate, grab a glass of wine after a home-cooked dinner and head to the private outdoor patio to continue your intimate discussions. Although you’re away from the hustle and bustle of the city, you’re only a few minutes walk to the nearest T station to get you downtown. It’s also pretty close to Boston College, so the surrounding neighborhood has a great college-town vibe.

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4. Modern Loft

Why you should stay: A great stay for a family near the historic Boston Freedom Trail.

Sleeps: 4
Minimum stay: 4 nights
Rates from: $315/night

Airy, modern, and bright: that’s how you’d describe this beautifully-designed 1700-square-foot loft in the true heart of the city. This modern loft is only one block from the State House, Boston Common, and the beginning of the Freedom Trail.

Whether you’re heading to a play in the Theater District, a cocktail bar in the North End, or walking along the cobblestone streets of Beacon Hill, this is very close to the action. Not exactly sure where to go? Don’t worry! The hosts have you covered with free use of their Boston guides to use during your stay. There’s only one bedroom, but thanks to a Murphy bed, no one has to bunk on the couch.

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5. Back Bay Penthouse

Why you should stay: Enjoy breathtaking Boston skyline views from the private rooftop deck.

Sleeps: 4
Minimum stay: 5 nights
Rates from: $400/night

An original spiral staircase invites you up to this newly renovated penthouse suite in a historic brownstone along the South End/Back Bay line. The classy and dramatic kitchen boasts glass subway-tiled backsplash, espresso cabinets, quartz countertop, and breakfast bar. Locals won’t be calling you a “chowdahead” (a.k.a. stupid person) by staying at this sleek and classy home. And Back Bay is one of the most exclusive neighborhoods in Boston – it’s a very fashionable place to stay.

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6. South End Condo

Why you should stay: A cute apartment that’s pretty affordable (by Boston standards, at least.)

Sleeps: 2
Minimum stay: 28 nights
Rates from: $178/night

Get cozy with your partner in this beautifully situated rental in the South End of Boston. With larger-than-life windows, the sun reaches every corner of this apartment. But don’t worry, there are room-darkening shades throughout to make sure you have a restful sleep. With the well-stocked pantry (including snacks and a bottle of wine for the hosts) you can save a few bucks and whip up a meal at home.

But you’ll definitely be tempted to head on out to Restaurant Row for some seriously good eats as it’s just around the corner from your apartment. (Again, this is one of the airbnbs in Boston that may change it’s minimum stay in the future, so be sure to check it case our editors forget to update the article.)

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7. Victorian Beauty

Why you should stay: Get amazing views of the Cochituate Standpipe.

Sleeps: 4
Minimum stay: 2 nights
Rates from: $150/night

Staying here is like walking into another country — and that country is Italy, to be exact. You’ll feel like you’re in the heart of an Italian vineyard when you arrive in the yard of this exquisite Victorian home. From its stone walls to the garden fountain, the exterior looks like it could be a historic Italian home.

But inside, it feels like an English country home, which makes it extremely relaxing. The roomy home has subtle colors and thoughtful touches (including a hand-painted door) that make this rental a rarity in Boston, especially considering reasonable starting price to sleep four.

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8. The Clare

Why you should stay: Live like you’re going back to college – as a well-to-do professor.

Sleeps: 2
Minimum stay: 3 nights
Rates from: $145/night

This fantastic brownstone is downtown and close to several universities, but since it’s a nice home on a quiet, tree-lined street, you’ll feel more like a well-respected professor than a college student sleeping in cramped apartment.

Many of the residents in the building are researchers and visiting instructors working on special projects, so you’ll fit right in if you want to rock a tweed jacket and thick-rimmed glasses. And working on your next research project (or Netflix binging, your choice) should be easy thanks to high-speed internet. If you need a break, just head outside to one of the many affordable college hangouts nearby.

Follow ’em: @theuptonboston

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9. 1800s Schoolhouse Retreat

schoolhouse airbnb boston — Photo: Airbnb

Why you should stay: Forget living like you’re going back to school – just live in a school.

Sleeps: 2
Minimum stay: 3 nights
Rates from: $150/night

The Schoolhouse Retreat is one of the funkier airbnbs in Boston for a few reasons – it’s totally Boho-meets-modern inside, and outside, you’ll notice something unique: it looks a lot like a school building. And that’s because it used to be one.

That means you get to sit at the cool kid table every day, though you may also want to take on the role of teacher and get some work done in the dedicated office space. And if you feel like ditching school all together, just head on out to the many restaurants and shops in the surrounding Charlestown neighborhood.

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10. The Asterisk

Why you should stay: Hello! It’s a private yacht.

Sleeps: 4
Minimum stay: 2 nights
Rates from: $260/night

Ever sit on the shore and wonder what all those rich people are doing on their beautiful boats in the water? Well, strap on that bikini or speedo, lather up the sunscreen, and stay on this 43-foot yacht. With two staterooms, there’s plenty of space for two couples to enjoy their newfound luxury.

Whether there’s a Nor’easter barreling down on the Boston harbor or record-breaking temperatures, this boat has heat and air conditioning to keep you comfortable. Finally, you get to see what life looks like on the water rather than washed up on shore. Just remember that you can’t actually set sail.

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Plan your trip to Boston, Massachusetts

There’s so much do in Boston that you can’t pack it all into one trip, so make sure to prioritize what kind of things you want to see. Here’s a few to consider adding to your list.

Boston built the first subway in the United States (in 1897) so make sure to take a ride on the T.
Grab some good food and souvenirs in the historic Faneuil Hall Marketplace and Quincy Market.
Hope on one of the infamous Swan Boats at Boston Public Garden.
Pop by Boston Common (also singular), next door to the Public Garden – it’s the country’s oldest public park.
If seafood is what you’re after try Atlantic Fish Co. or the Barking Crab.
Go on the free tour of the Sam Adams Brewery and then hang out in the tap room to grab yourself a pint of one of the iconic seasonal beers.
If sports are on your mind, you’ve got your pick with football (New England Patriots), hockey (Boston Bruins), baseball (Red Sox), or basketball (Celtics).
Take a jaunt just outside city limits and take a hike on some of these amazing trails.
Grab a beer of the best Irish pubs in the country including The Burren and The Tavern at the End of the World. But don’t count on any two-for-one specials: they’re illegal in Boston.