Looking for airbnbs in 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 will be pretty simple; the hardest part may actually be deciding where to stay in Massachusetts!
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 in MA allow you to really feel a part of the community that you are staying in, and some MA vacation rentals 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!
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 these cool VRBO rentals and best Airbnbs in Massachusetts.
Top Airbnbs in Massachusetts
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 Massachusetts 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!
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 MA 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 MA 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 MA 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 MA 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 MA Airbnb 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 can show you 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 Cape Cod 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 in Massachusetts? Look no further than this phenomenal Airbnb cabin 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 this MA treehouse.
If you are looking for unique, interesting, and absolutely breathtaking, this is the Airbnb treehouse for you!
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 don’t want to compromise 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 vacation rental is one of the best Airbnbs Massachusetts has!
Lakeside Four Season Home in Brimfield MA
Brimfield is known for its crystal-clear spring-fed lake, Little Alum Pond, and this Massachusetts 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 on the lake.
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 from this lakeside MA Airbnb!
Provincetown Perfection in Provincetown MA
Visiting Provincetown? This Airbnb, called “Provincetown Perfection” can host four guests and is located a short walk away from the water. Amenities are abundant, including air conditioning, free parking, wifi, and a smart TV.
The home’s inside is decorated with bright nautical decor, including fun wave paintings on the walls and even a TV stand decorated with a crab and turtle. Guests will also have access to an outdoor patio with furniture and a washer and dryer, making this the greatest accommodation for a more extended stay.
Check out more of the best Airbnbs in Provincetown.
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 a MA Airbnb that offers a little taste of country paradise!
Jaw-Dropping Mountain & Lake Views in Great Barrington MA
Not only does this Massachusetts VRBO 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 VRBO offers a little taste of private mountaintop paradise!
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant! in Nantucket MA
When it comes to Nantucket vacation rentals, this gorgeous cottage is one of the best! It sleeps up to 4 and it’s perfectly situated next to several fun Nantucket things to do, like Children’s Beach. This cottage vacation rental is quintessential Nantucket all the way!
Cozy hidden gem, 2 bdrm house with walk to beach in Provincetown MA
This adorable Provincetown vacation rental can sleep up to four but the big draw here is of course, the private beach that is just a short walk away! Could you imagine a Cape Cod getaway where you can take a little stroll from outside the door of your MA VRBO and have your feet in the sand in just a few minutes? Sounds pretty spectacular over here.
Oak Hill House in New Marlborough MA
This gorgeous updated Airbnb in the Berkshires is the perfect vacation rental for anyone planning on a Berkshires vacation. With three bedrooms and three bathrooms, this MA Airbnb can sleep up to 8 and is located on 12 wooded acres in the Berkshires.
Also onsite is a woodburning fireplace, outdoor fire pit, and a hot tub. How fantastic does this Berkshires Airbnb sound, especially for a winter getaway spot?
Read these next:
- 50 Things to Do in Massachusetts: Your MA Travel Guide
- 15 Glorious Nantucket Airbnb Rentals
- 12 Amazing Airbnbs in Martha’s Vineyard
- 20+ Best AirBnbs in New England: Treehouses, Cabins, & More
- 10 Unique Airbnbs in Connecticut: Boats, Treehouses, & More
- 12 Best Hotels on Cape Cod: Where to Stay on the Cape
- 10 Charming Cabins in the Berkshires
- 13 Best Airbnbs in the Berkshires
- 10 Best Hotels on Nantucket: Where to Stay for a Nantucket Getaway
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 writes 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, son, and cats, & drinking a maple latte.