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Planning a visit to Massachusetts? The Bay State has plenty to offer, whether it’s a romantic getaway, a coastal lighthouse tour, or a fun fall adventure through some of the best leaf-peeping spots in the state, planning what you want to do on your Massachusetts vacation will be pretty simple; the hardest part may actually be deciding where to stay!
Sure, you could stay in a chain hotel and have a perfectly fine time, but why go for fine when you can go for extraordinary? Airbnbs allow you to immerse yourself in the community that you are staying in, and some Airbnbs offer unique and interesting experiences that you would be hard-pressed to find in any sort of hotel chain, like… oh, I don’t know, maybe staying in an octagonal glass treehouse might be one!
A Massachusetts vacation is always bound to be a good time, but you can send it right over the top by choosing from one of the following 14 fantastic Airbnbs in Massachusetts:
Please note: As an Airbnb Associate, I earn when you book through these links.
Romantic Ocean/Boston Views in Swampscott, MA
Let’s say you are planning to sweep your significant other off of their feet with a spectacularly well-thought-out romantic getaway; would a completely private, whole apartment rental on the bay with a fireplace and a hot tub work well as a place to lay down your head each night? Yeah, I think so too!
This gorgeous Airbnb is decked out with a cool coastal vibe and even has a custom chef’s kitchen so you can feel like a pro when you whip up a little something in that amazing kitchen before heading out to enjoy the beautiful ocean views from the wraparound balconies. Kitchen and bathroom essentials, Wifi, and the first breakfast are provided, too. With Salem, Marblehead, and Boston within a half hour’s drive, and Rockport just about 45 minutes away, this Swampscott Airbnb is an excellent landing spot for all kinds of Massachusetts adventures!
Home Above the Trees in Wellfleet, MA
This custom build on the Cape is nothing short of breathtaking! This home can sleep 6, meaning you and a few of your closest friends can come out to this beautifully designed property for the perfect friends’ getaway on the outer Cape. Plus, all kitchen and bathroom essentials are provided and there is Wifi throughout the property.
Lounge around on Wellfleet’s beautiful beaches or explore the nearby Great Island Trail, named one of Massachusetts’ best hikes, and when you return you can freshen up in the gorgeous—and private!—outdoor shower before deciding what you want to do next; you might just decide to stick around and enjoy the stunning sunset views from the upper deck as you and your friends relax in the swinging hammocks, surrounded by a lush canopy of trees. Comfortable, yet chic, the Wellfleet Home Above the Trees is a one-of-a-kind Airbnb on the Cape.
Sunset Bliss-Plum Island beauty in Newbury, MA
Aptly named, Sunset Bliss is a stylish and standout beach cottage on Plum Island that offers stellar water views of the marsh, and a short five-minute walk to the beach (snorkeling gear provided!) Smartly furnished, this Airbnb can sleep up to 5 guests and has a sophisticated, yet comfortable coastal aesthetic.
Unique features of this Plum Island Airbnb are the brick floors and exposed beams that really rev up some of the coastal cool aesthetic that this cottage has. Light a fire in the wood-burning fireplace after watching the sunset and kick back and relax in this charming, freshly renovated beach cottage. Wifi and kitchen and bathroom essentials are provided. Oh, and if you happen to have an electric car… this Airbnb has an electric car charging port, too!
Brooksong, the Perfect Berkshires Getaway in Dalton, MA
What makes Brooksong the perfect Airbnb for your Berkshires getaway? Plenty! This Airbnb can sleep up to 10 guests, so you can bring the entire party with you to this one. Brooksong has many interesting features, including a 1920s antique bar, a pool table, and an outdoor fire pit. Kitchen and bathroom essentials are included and yes, there’s Wifi here, too!
Brooksong is named after the nearby brook, but Dalton has plenty of things to do while you stay in this beautifully updated historic charmer! The Berkshires will always be a tested and true vacation destination and Brooksong might just be the perfect landing pad for your Berkshires getaway!
Boston Harbor Yacht in Boston, MA
Airbnbs often offer a chance of experiencing a different way of life than you might be used to, and this Boston Harbor yacht offers you the opportunity to see what living on a yacht is like! Named the Sea Pearl, this yacht is kept sparkling clean and well-appointed with a coffee maker, microwave/convection oven, and a toaster for guests to use (cooktop unavailable due to insurance restrictions) year-round, so you can stay on the Sea Pearl any time of the year, including Christmastime when Boston is full of the magic of the season. Some kitchen and bathroom essentials are provided. Plus, there’s Wifi!
The yacht cannot leave the harbor, but it is completely walkable to the North End, Bunker Hill, and the USS Constitution, and an easy Uber ride to any number of fun Boston activities, coffee shops, etc.
Waterfront Oasis on the Cape in Bourne, MA
This Cape Cod charmer is all that comes to mind when you think of relaxation by the sea; with only 8 other homes on this causeway-accessed island, you will be in your own private waterfront haven while you enjoy the stunning scenery of Buzzard’s Bay from the wraparound porch of this beautiful Airbnb. Kitchen and bathroom essentials are provided, and there is Wifi, as well.
This lovely waterfront dwelling can sleep up to 7 guests, and the hosts also provide kayaks for your use so you can get out on the water for yourself! Beaches for swimming are within walking distance and there is also an outdoor shower for rinsing off after playing in the water, and a grill for cooking up your favorites as you settle in to watch the spectacular sunset across the water.
Octagonal Glass Treehouse in Otis, MA
Looking for a one-of-a-kind stay? Look no further than this phenomenal Airbnb in the Berkshires! Floor-to-ceiling windows allow you an unfettered 360-degree view of the 7 acres this octagonal glass tree house rests on. This unique home manages to be both spacious and cozy with a wood-burning fireplace and expansive views that are impossible to grow tired of.
Kitchen and bathroom essentials are provided, and the treehouse is ideally situated in the Berkshires for many activities, including wintertime skiing, summer sight-seeing, and Berkshires must-do activities like Tanglewood and The Norman Rockwell Museum less than a half an hour up the road. Wifi is also available in the treehouse.
If you are looking for unique, interesting, and absolutely breathtaking, this is the Airbnb for you!
Glamping in Hephzibah Campground in Chester, MA
When you’re looking for something off-grid but you still want access to some of the creature comforts like a shower, toilet, and a bed, then this Airbnb might be the right choice for you! You can unplug and relax off-grid with no electricity or Wifi, but still have some modern niceties like fairy lights that illuminate the deck at night so you can kick back in style to enjoy the solitude of this private and well-kept campsite.
This glamping opportunity even offers a lovely wood stove in the tent so you will have no problem keeping toasty warm at night in the queen-sized bed provided! A charcoal grill and outdoor “kitchen” supplies are provided, so bring your s’mores ingredients so you can roast marshmallows over the fire pit in this unique Massachusetts Airbnb.
Rustic Berkshire Getaway in Otis, MA
This upper-floor apartment that sleeps 4 in Otis, MA is just what you need when you are looking for something with a quaint, rustic feel but are uninterested in compromising on comfort, convenience, and Wifi! Kitchen and bathroom essentials are provided, including access to a washer and dryer if you need to clean up after a long day out and about exploring the Berkshires.
Perfectly situated as a cozy country retreat to let you relax and rewind with a beautiful second story view of the beauty of the Berkshires, this rustic Massachusetts Airbnb might just be the perfect option for you!
Artist Cottage in Great Barrington, MA
This lovely little historic cottage in the village of Great Barrington is without a doubt, one of the coolest Airbnbs in Massachusetts! It has a fireplace, a wood stove, an outdoor jacuzzi, and a soaking tub in the bathroom that has a skylight window above so you can bathe in the sunshine during the day or under the stars at night.
This quaint cottage can sleep two, is Wifi equipped, and provides kitchen and bathroom essentials, plus an added extra: an art studio with sink and art supplies. Artist or not, this lovely Airbnb is a perfect match for anyone looking for a beautiful stay in the Berkshires!
Lakeside Four Season Home in Brimfield, MA
Brimfield is known for its crystal-clear spring-fed lake, Little Alum Pond, and this Airbnb gives you a front-row seat to spectacular four-season views of the lake, plus access to a pedal boat, fishing boat, and snorkeling gear if you would like to get out and experience the tranquility of this pristine lake up close and personal.
The Lakeside Four Season Home can sleep up to 6 people and is well-equipped with kitchen and bathroom essentials and Wifi. Décor is a comfortable, clean, homey style, but you won’t be paying too much attention to the interior with lovely Little Alum Pond just steps away!
Baker Pond Hideaway in Charlton, MA
Baker Pond Hideaway is nestled away in the woods in Charlton and is an apartment rental that can sleep 5 with its own separate entrance that leads to beautiful Baker Pond. The hosts of Baker Pond Hideaway prefer to meet their guests as they arrive to ensure you have absolutely everything you might possibly need for a perfect stay in this clean and cozy apartment.
Amenities include Wifi, kitchen and bathroom essentials, a gas grill, fire pit, outdoor seating, and access to fishing gear, bikes, kayaks, a canoe, and a paddleboat for exploring the pond. Snowshoes are available in the winter if you’d like to explore the winter wonderland woods around this beautiful home, too. Baker Pond Hideaway is an excellent choice for anyone looking for an Airbnb that offers a little taste of country paradise during their Massachusetts getaway!
Jaw-Dropping Mountain & Lake Views in Great Barrington, MA
Not only does this Airbnb have jaw-dropping views outside, but the entire house is a sight to see! This modern cabin paradise has tastefully decorated rooms and high-end appliances and can sleep 9. The kitchen and bathroom are both stocked with all the essentials and this private mountaintop home offers Wifi throughout the property. Highlights include a pergola, a hot tub, hammocks, a fire pit, and a grill for you to enjoy the incredible outdoors with.
The hits don’t stop coming, either; there is a screened sunroom with stellar views of the lake if you’d like to snuggle in on the comfy sectional with your morning coffee and watch the sunrise over the lake. This Great Barrington Airbnb offers a little taste of private mountaintop paradise!
Historic Townhouse in Center of Boston, MA
This historic Boston townhouse near the North End is an absolute stunner! Sleeping 6, this Airbnb is nothing short of perfection for anyone looking to stay in the heart of Boston within easy walking distance of the action of the city! You want to be able to hang out on the balcony and enjoy the music from the nearby nightlife? Check. Would you like to roll out of bed in the morning and make your way to any number of cute coffee shops easily? Check. How about staying in a townhome that has done a phenomenal job of preserving historical features such as original brick and beams and antique pieces while still updating the space and making it feel fresh, hip, and modern? Absolutely check.
Amenities include kitchen and bathroom essentials and Wifi throughout the space. If you are looking for a way to immerse yourself in the city during your Boston getaway, look no further because this historic townhouse is the perfect Airbnb for you!
Read these next:
- 20 of the Best Airbnbs in Maine You’ll Want to Book Now
- 20+ Best AirBnbs in New England: Treehouses, Cabins, & More
- 10 Unique Airbnbs in Connecticut: Boats, Treehouses, & More
Amy is the founder of New England with love. A proud Vermonter, she hopes to share her love of New England and help you find the best adventures in the region. Amy is also blogger/founder at Two Drifters, where she blogs alongside her husband about romantic and couples travel, relationships, honeymoons, and more. When not working on websites, Amy is probably reading, cuddling with her husband and cat, & drinking a maple latte.