Also known as the Commonwealth of Massachusetts, it is the most populous state in the New England region of the northeastern United States. As of 2019, it had a population of 6.893 million. Boston is its capital, with various well-known attractions like the Museum of Fine Arts, Boston, Boston Common, and Boston Public Garden. Other top sights include the Faneuil Hall Marketplace, Fenway Park, and the New England Aquarium. Visitors who are looking to do something physical can challenge themselves to climb the Pilgrim Monument in Provincetown. To get your heart pumping, take a thrill ride with Codzilla across the Boston harbor. But before sightseeing can happen, you will need a place to stay. Read on for a list of the top short term rentals in Massachusetts, USA.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and short-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on August 31, 2025.
1. Expanded farmhouse along Shearer Road (from USD 3515)
This expanded farmhouse is situated in a rural village in the Pioneer Valley of Western Massachusetts. There are 6 bedrooms and 3 bathrooms that can accommodate up to 12 guests. You get a fully equipped kitchenette with basic cooking ingredients provided. There are several decks and outdoor patios with stunning views of the surrounding greenery. Feel free to use the hot tub, pool, and spa when they’re available. The washer and dryer are also available on-site.
Colrain, Massachusetts, United StatesSuperhost
Accommodates: 14
Top guest reviews
Host:
ed is a wonderful hosted was such a gracious host responding to questions all weekended was extremely helpfulthey were responsive and very helpfulbecca and ed are awesome hosts very responsive to questions and super helpfulLocation:
the location is so convenient near great hiking trails and the best local grocerbeautiful location especially if you're looking for something a bit remote and in the outdoorswe would definitely consider staying there again if the location worked out for the familythe hilltop haven was the perfect location for our family weekended’s place is breathtaking it is big and beautifulCleanliness:
amazing views beautiful clean house and a great hostRead more reviewsAmenities & Room:
nice house with an amazing view and a great pool beautiful outdoor spacewake up to spectacular views cooking is a joy the well appointed kitchen with viking stovefantastic views; attentive host; comfortable beds; big common spaces; toys for kids and sports equipment available for freethe kitchen was extremely well stocked and the appliances were moderngreatly enjoyed the pool and hot tub as well as the fire pit and charcoal grillWeekly discount: 20% off
2. Homey cottage overlooking Big Alum Pond (from USD 676)
The entire cottage has a rustic vibe to it. Set along Big Alum Pond, it’s about an eight-minute drive to Old Sturbridge Village. There are two bedrooms with six beds and a bathroom. This cottage can sleep up to six guests. The kitchen area features a sink, stove, oven, a microwave, and a full refrigerator. The kitchen leads into the dining area and living room with picturesque views of the lake. Please note that there is no air-conditioning, however, fans are available.
Sturbridge, Massachusetts, United StatesAccommodates: 6
Top guest reviews
Host:
she was a very helpful and responsive hostsusan was a really wonderful host and we would love to stay here againextreamly fast and responsive to email or any questions i hadneighbors were friendly always returning a smile or a wavethe neighbor was very friendly as well as many boaters who went past with a waveLocation:
great location right on the waterthe location is perfectly situated near great local attractionsthe location is fantastic the lake is so closeit was easy to find and close to townthere are plenty of beds to invite close friends or family to joinCleanliness:
it's clean and charmingperfect spot clean advices venuesreally enjoyed this beautiful clean lakethe lake is beautiful and cleansue was very thorough on new cleanliness protocol and responsive to any questions we hadRead more reviewsAmenities & Room:
the house was rustic but very comfortable with plenty of rooms and beds for usWeekly discount: 15% off
3. Private island retreat (from USD 1633)
You will find yourself in the woods at this two-bedroom cabin. Recent guests who have booked this accommodation have given a five-star rating! There is one double bed, three single beds, and two sofa beds in this cabin. It has a living space that’s great for up to eight persons. The bathroom is small with a shower and sink. Pets are allowed! Do note that there is an early check-out time at 10 am.
Douglas, Massachusetts, United StatesAccommodates: 8
Top guest reviews
Host:
jason (on site manager) was extremely helpful and super nicewe had a great time here and the hosts were very helpful and niceLocation:
the island is a neat location to spend a relaxing vacationRead more reviewsCleanliness:
the main cabin is larger than i expected clean and functionalWeekly discount: 6% off
4. Lovely guesthouse at Sagamore Beach (from USD 135)
This lovely guesthouse has a private entrance. It has one bedroom with a king-size bed, perfect for couples. There are room darkening shades considering how early the sun rises near the apartment. Feel free to access the outdoor space and gardens. You can also have a barbecue session in the private outdoor courtyard with a grill and fireplace. Washer and dryer facilities are available on-site.
Sagamore Beach, Massachusetts, United StatesAccommodates: 2
Top guest reviews
Host:
sheila was an amazing host very quick response when we had questionsshe was vey accommodating and friendlysheila was an awesome hostlovely host who was there if you needed hersheila is a great airbnb hostLocation:
the location is ideal only a 5 minute walk to the beachsuper cute cottage that is a close walk to a public beachwalking distance to the beach and close to other fun cape cod townswe found the neighborhood to be quiet and charming sagamore beach was literally a five minute walk awaycute guest house great location and just a couple minutes from the beachCleanliness:
very clean and sheila is super friendlythe place was very clean and had everything listedthe house was very clean and invitingit was very clean and had everything you neededthe place was clean cozy and so convenientRead more reviewsAmenities & Room:
the guest house is exceptionally comfortable and beautifully decorated with new furniture and accessoriesgreat location plenty of amenities and a very comfy bedwe had a great stay at sheila’s lovely apartmentsheila’s place was lovely - very spacious for two people while still being cozyWeekly discount: 10% off
5. Quiet cabin near Williamsville Pond
This cabin for up to four guests is situated close to Williamsville Pond. There is one master bedroom with an ensuite bathroom. You can find a half bath on the first floor of the cabin. With that said, stairs climbing is necessary to get around the house. Chill by the firepit in the evening or sit on the deck during the day and watch the calm waters flow. When the temperature is right, kayak on the waters and explore the neighborhood. This place is not suitable for infants under two years old.
Hubbardston, Massachusetts, United StatesTop guest reviews
Host:
amy was a wonderful hosttara was a great hostthey were very responsive and generoustara is a very responsive hostjust like you want a property owner to be when you’re on vacationLocation:
location is private and peacefulmany cute places around like alpaca farm and antique shopsthis place is an amazing get away with family or just a romantic weekendif you like to fish this is the place for youwe would definitely recommend this placeRead more reviewsAmenities & Room:
we loved having wine and cheese every night by the water (in very comfortable chairs)
6. Studio cottage in East Brookfield
This studio cottage is right by Lake Lashaway. There are a full-size bed and futon that can sleep up to four guests. All cooking utensils, blankets, pillows, sheets, and towels are provided during your stay. Outdoor amenities include a gas grill, picnic table, seating areas, and parking spaces. There is a private dock where you can access the waters. Feel free to use the kayaks or your own boat or jet-ski. Pets are allowed but do request for approval before booking.
East Brookfield, Massachusetts, United StatesAccommodates: 4
Top guest reviews
Host:
the hosts are awesome peopleowners provided a helpful list and suggestions when we inquiredhosts were very generous and thoughtful and it was just what we neededthey were friendly and helpful but never intrusiveLocation:
it is a wonderful location to sit back and relax leaving the busy ness of life behindthe lake cottage is adorable and close to everything you need but far away enough to be an escapenice touch was a discount coupon to a great restaurant within walking distancethis is a great cottage in the perfect location on the lakeCleanliness:
super clean and right on the lakewater was clean and not rocky and we had a rowboat and kayaks to fish withand the cottage was perfectly cleaned and prepped for our stayvery cute clean and comfortable cabinRead more reviewsAmenities & Room:
the cottage has everything needed for a comfortable vacationtravelers can expect great hospitality and amenities at this cute comfy cozy cottage on lake lashaway
7. Three-bedroom house by Fort Meadow Reservoir
This three-bedroom house is located right in front of the Fort Meadow Reservoir. There are several beds for up to eight persons and two bathrooms to use. One of the bathrooms comes with a hot tub hot tub. You will get a gift basket or a bag of goodies from the host upon arrival! How sweet of the host to prepare that to welcome you to Massachusetts. The paddleboard and kayaks are free to use. Life jackets are provided as well. Do note that a friend of the host occupies the basement but you have access to the rest of the house.
Marlborough, Massachusetts, United StatesAccommodates: 8
Top guest reviews
Read more reviews
8. Cottage close to Hamilton Reservoir
There are two bedrooms in this clean and tidy cottage. One bedroom comes with a queen-size bed while the other one comes with a double bed. There is a full kitchen with cooking amenities and a living room with a propane fireplace. The accommodation also has child-friendly items like a stroller, foam floor tiles, coloring books, and a bathroom step-stool. You will be steps to the lake.
Holland, Massachusetts, United StatesAccommodates: 4
Top guest reviews
Host:
she's a great hostgabby was an amazing hostgabby was very responsive to any questionsgabby is probably one of the best hosts i’ve had ever and had amazing hospitalitythe booklet and basket of information was welcome and helpfulLocation:
the location is super convenientgreat location right off the highwayi highly recommend renting this cute little placeit's nice to be close to everything but get that far a way feelingwonderful place to get away and relaxCleanliness:
super clean updated and quaintgabby’s place was clean and cozygabby place is clean and elegantthe house is very clean and quiteher house was clean comfortable and welcomingRead more reviewsAmenities & Room:
super peaceful back deck with a great grill and table with a firepitgabby's cottage is charming and comfortablethe maybrook cottage was the perfect mix of cozy and chicwhat more could you want? a cozy cottage with fireplace lake views and all amenities? yes to allwe especially loved the jetted bath tub and fire table
9. Spacious apartment in the Red Rocks Conservation Area
This one-bedroom apartment is attached to the host’s home. But you get a separate entrance and personal parking spaces. You will receive the keys from the host upon arrival. The bedroom has a queen-size bed and a baby cot is available in the common spaces. There is a short flight of stairs to the entrance. Good Harbor Beach is about an 11-minute drive away.
Gloucester, Massachusetts, United StatesAccommodates: 3
Top guest reviews
Host:
the hosts were very kindour hosts were quick to respond and very helpful with our questionshosts are incredibly kind and offer great suggestions for fun things to dowe really enjoyed staying here and the hosts were very kindrachel is very responsive to messages and very helpful with local infoLocation:
nice secluded area close to towngreat location in a nice quiet location that is just a quick few minutes' drive to townawesome space super close to downtown and very spaciousreally close to beaches and downtown but also a nice quiet getawaya nice and quiet place at walking distance from a park (walk/run)Cleanliness:
very clean and spaciousa very great place very clean the bed is very comfortablequiet clean and spacious very easy to findbeautiful spacious and very clean private space in west gloucesterthe apartment was super clean and well equipped for our little familyRead more reviewsAmenities & Room:
comfy bed good ac helped in muggy weatherthis space has so much room we loved having our own entrance and all of the rooms were large
10. Treehouse in West Stockbridge
Are you up for a treehouse living experience? There are three bedrooms in the treehouse. It comes with a king-size bed, a double bed, and a bunk bed. There are two bathrooms in total. The accommodation can fit up to five guests. You will find yourself less than a 10-minute drive to Tanglewood, a live music venue. Kripalu Center For Yoga & Health is also within the vicinity as Tanglewood.
West Stockbridge, Massachusetts, United StatesAccommodates: 5
Top guest reviews
Host:
ben was very accommodating and responsive to questionsthe instructions were clear and easy and the hosts respond quicklyLocation:
really cute "treehouse" type lodging walking distance from the historic village of west stockbridgegreat value wonderful space for dogs great location and very privateben's place is perfect for a romantic getaway or a family and friends tripCleanliness:
wonderful spot clean comfy and spaciousthey have multiple bedrooms/beds and bathrooms and the house itself is very clean nice and comfortablethe house is very clean and comfortable as others have saidben’s place was reasonably priced clean and in a perfect locationRead more reviewsAmenities & Room:
the beds were super comfy and we all slept well in them
A quiet retreat awaits
The top short-term rentals we’ve shown you thus far are situated in quiet neighborhoods. We especially love the houses near the lake like the quiet cabin near Williamsville Pond, homey cottage overlooking Big Alum Pond, and the three-bedroom house by Fort Meadow Reservoir. We’re also eyeing the rental houses set in the forest, like the two-bedroom cabin in the vicinity of Breezy Picnic Grounds Waterslides and the treehouse at West Stockbridge. What about you?
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data