Are you planning a trip to Boston, Massachusetts? This city, known for its delicious seafood and top-notch sports, is one place you won’t want to miss.
Sure, Boston has incredible boutique hotels and places to stay that are perfect for families, pet friendly hotels and hotels with in room jacuzzis, but Boston vacation rentals can offer all these things too in a way that makes you feel like you’re really diving in and getting a good taste of that local flavor!
Whether you’re new to Boston or visiting for the second or third time, staying in an Airbnb or VRBO property can make your experience even better. Not only will you be able to have a lot more space to yourself, but you can also cook your own meals (and maybe save your travel budget for more fun tours around town!) and experience what it’s like to live in the city.
Here are some of the best Boston vacation rentals that you should consider booking during your next visit to the City on a Hill.
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Boston Vacation Rentals
ASTONISHING 1 BEDROOM PARLOR, WELL APPOINTED, -SOUTH END BOSTON -BEST LOCATION
This beautiful rental apartment is located in one of the best areas of Boston: Southie! It’s a one-bedroom apartment best suited for up to two guests at a time, therefore making it the perfect vacation rental in Boston for a couple’s retreat.
The street that the apartment is located on is lined with Brownstones, the most charming buildings in all of Beantown. The apartment has a comfortable yet modern atmosphere and features a full kitchen, breakfast bar, Keurig maker, and living room with a flat-screen TV.
With a short T-ride, you can easily get to downtown or the Fenway neighborhood.
Luxury Beacon Hill 1050 Sf Condo With Private Patio/Garden And Private Entrance
Newly renovated, this Beacon Hill vacation rental is spacious, private, and very comfortably furnished, but the real allure of this property is the dreamy outdoor space! The patio is a private landscaped space that is absolutely ideal for dining al fresco.
This vacation rental is spacious at 1050 square feet, but it only sleeps up to 2 and would be great for either solo or couples travel!
Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston
Located in historic Beacon Hill, this beautiful VRBO is just steps away from North End and all its fantastic restaurants (and cannoli!) The entire property is historic, with exposed brick walls and antique touches that add to the ambiance.
This VRBO is a roomy 1300 square feet and can sleep up to 4, so it could be perfect for a friends couples trip!
Newly Designed Loft-Fast Wifi-Pet Friendly
This one bedroom, one bath sleeps two in downtown Boston, perfectly situated for downtown Boston adventures! Book this newly designed loft if you’re looking for a great pet friendly vacation rental in Boston.
Bright & Spacious Loft Steps to the Freedom Trail
With 1,000 square feet, this apartment is bigger than many other area vacation rentals! It can host up to four guests and is located a short walk away from the beautiful Boston Common, the central park, in the downtown area.
The apartment has huge windows that add tons of natural light, and there is chic and stylish furniture throughout. While the apartment is simplistic, pops of color help to give lots of character to the apartment.
If you are a fan of shopping, this apartment is located in the best possible spot. Downtown Crossing is right at your doorstep!
Romantic Ocean & Boston Skyline Views – From an Exclusive Outdoor Hot Tub!
If you want to see ocean views every day you wake up at your VRBO, this is it! Located just a quick drive out of the city, this property has even more going for it than just ocean views, too… this is one of the top Boston VRBOs with a hot tub!
In fact, there are even more incredible features at this VRBO, like a piano, fireplace, and Chef’s kitchen, perfect for whipping up a romantic, intimate meal for your significant other!
3 BR, 3 BTH. 2 parking. Harvard/MIT/Tufts/Casino
Somerville is a suburb that is home to some of the best universities in the area, and while this part of the Greater Boston area feels a bit less like a city, you can hop on the Red Line T and get to downtown within twenty minutes.
This spacious home can host up to six guests at a time. It has three bedrooms, three bathrooms, a living room, full kitchen, office, washer and dryer, and a patio. There is also free parking at the apartment, so if you drive to the city, you’re in luck!
The home’s interior is very rustic and cozy, with warm and cool tones throughout and chic furniture and decor.
*Fort Hill Inn-Boston* Cozy, L@@K Comfortable, Studio/Suite..Minutes to Center!
This conveniently located Boston VRBO is located in the residential Fort Hill neighborhood in a Historic Victorian Brick Row House, just a quick walk to public transportation that will take you anywhere you want to go!
Quaint and cozy, this vacation rental can sleep up to 4, but heads up: no kids or pets allowed!
Walk To Fenway, Private Home, Perfect Location!
Looking for accommodation for 11? This private Boston townhome could be perfect for you. Located in Brookline, this townhome has three bedrooms, three and a half bathrooms, a massive kitchen, a living room, and even a fireplace.
The inside of the townhouse is incredibly unique. The majority of the interior has exposed brick walls, giving the apartment a very industrial feel. While the apartment is mostly simplistic, it has pops of color throughout.
While it’s located in Brookline, this Boston VRBO is right next to Back Bay, Coolidge Corner, Longwood, and Fenway!
Stunning South End/Back Bay Penthouse
When staying in a city, there is no better place to stay than in a penthouse. That’s what makes this apartment in Southie such a great place to stay! It can host up to four guests at a time.
Inside this Boston Airbnb, there are two bedrooms, one and a half bathrooms, a full kitchen, and a living room. All guests will also have access to the rooftop deck, which offers breathtaking views of the city skyline, especially at sunset!
The apartment was recently renovated a few years ago and is right next to public transportation in the city.
Panoramic view, large deck, ground floor apartment, walk to subway and beach
Located in a quiet, residential neighborhood, this cozy apartment is beautifully and comfortably furnished to be the perfect home away from home! Public transport is nearby, so no need for car, but if you did bring your car, there is on street parking.
This Boston VRBO only sleeps up to 3, but it would be perfect for a couples getaway. The most enticing aspect of this vacation rental is the gorgeous outdoor space and being within walking distance of the water!
“Travelers’ Choice Award” Green Turtle I Houseboat in Boston Harbor!
Looking for unique VRBOs in Beantown? This houseboat in Boston Harbor is one of the coolest Charlestown vacation rentals!
Sleeping up to 2, this cozy little houseboat offers the perfect couples escape for those in Boston looking for a unique vacation rental.
4-story Central Luxury-two blocks to Boston Common
Luxurious townhomes are hard to come by in Boston, so if you have the opportunity to stay here, jump on it! This home in Bay Village can host up to seven guests at a time and is incredibly spacious.
There are three bedrooms, three bathrooms, a big living room, a dining room, a full kitchen, and even a patio. The interior is very minimalistic yet luxurious and has fun artwork throughout to help give the townhouse character.
Guests will love the fun amenities that come with this apartment, including a piano, guitar, wireless speaker, and even tons of free cereal and fruit for breakfast.
Gorgeous Beacon Hill 1 BR | 1 BA
This gorgeous Beacon Hill Boston Airbnb is perfect for up to three guests at a time. It’s situated right next to downtown and the West End, so guests will love the central location.
The apartment boasts one bedroom, one bathroom, a living room, a washer and dryer, and a full kitchen. There’s even a huge walk-in closet, which can come in handy if you visit Boston for a longer period of time.
Guests have loved staying in this apartment, not only because of the location but also because of how kind the host is!
Historic Townhouse With Modern Amenities, Ideal Location in Center of Boston
This Boston VRBO townhouse is historic yet updated, and perfectly located for fun in the city! Just steps away from major attractions like the Freedom Trail, Faneuil Hall, Quincy Market, and fantastic North End fun, this is the perfect place to set up for a Beantown vacation.
This three story historic property is 1600 square feet and sleeps up to 6, so this could be the perfect place to stay for a friend trip to the city!
Now you know a few of the best vacation rentals in Boston! No matter which one you decide to stay at, I can guarantee that your trip to Boston will be one that you’ll never forget. Consider going to a Boston Red Sox or Boston Bruins game to make your trip even more memorable, and don’t forget about all the fantastic historical sights like the Paul Revere House, North Church, and Faneuil Hall Marketplace, that are a must-visit during a Boston trip!
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- Where to Go for the Best Breakfast in Boston
- Boston Slang: 30 Wicked Cool Boston Sayings You Should Know!
- 18 of the Best Free Things to Do in Boston
Amy Hartle is the founder and Editor-in-Chief of New England With Love, a comprehensive resource for travel in the New England region. Amy has been exploring New England since 2001. She lived in Vermont for many years and is a graduate of Plymouth State University in New Hampshire. Amy has been writing about travel for over a decade. On this site, Amy aims to share her love of New England and help you to have the best possible adventures!
Amy has been a full time blogger since 2012, and is also the publisher of Two Drifters, where she writes about couples travel and relationships, as well as Let’s Adventure Baby, a family travel site. When not traveling the world or creating epic blog content, Amy can be found cuddling with her husband, son, and cats, & drinking a maple latte.