Situated in the northeastern United States, Massachusetts boasts a varied geographical landscape, encompassing vibrant coastal regions, picturesque mountains, and fertile valleys.
Begin your exploration in eastern Massachusetts, where the bustling city of Boston takes center stage. Venture south to find Cape Cod and lay back in one of its charming coastal towns with stunning beaches. Head westward and you’ll come across the mountainous Berkshires, renowned for its forests, lakes, and hills. Moving to the central part of the state, you’ll arrive at the fertile Pioneer Valley defined by its charming college towns and the mighty Connecticut River. In the northeastern corner of Massachusetts lies the historic city of Salem, which is infamous for the witch trials of the 17th century.
Explore the state in style and ultimate comfort by staying in a luxurious accommodation. For great options, scroll down for the top luxury Airbnbs in Massachusetts, USA.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to luxury services and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 28, 2025.
1. Luxury villa with pool; Brimfield (from USD 7427)
This luxurious villa offers a pool and an array of upscale amenities ideal for big families, especially those with little kids. Take advantage of the provided crib, children’s books, and toys. A high chair, changing table, outlet covers, and board games are also available.
You can watch your favorite shows on the cable TV or engage in friendly competition with a thrilling game of ping pong. Immerse yourself in a captivating book from the available collection. Indulge in a relaxing bath in the bathtub or freshen up with the invigorating shower gel provided.
Brimfield, Massachusetts, United States
4.13 km (2.6 mi) from Old Sturbridge VillageAccommodates: 14
Top guest reviews
Read more reviewsCleanliness:
the house was very clean and the caretaker made sure that we’d wake up to a clean pool
2. Stunning home with heated pool; Becket (from USD 534)
This freshly renovated home sits in a premier location with access to the beach and lake where you can enjoy sandy shores and leisurely strolls. Take a dip or swim laps at this stunning property’s heated in-ground pool.
The home highlights a chef’s kitchen that allows guests to prepare gourmet meals. Stay connected with WiFi and pocket WiFi available here, perfect for either work or leisure. You can freshen up your clothes with the washer and dryer. Find all the essentials including towels, sheets, and toilet paper at the rental. Relax in the serene, well-maintained backyard, complete with comfortable outdoor furniture and a grill for preparing barbecue dinners.
Becket, Massachusetts, United States
84.51 km (52.6 mi) from Old Sturbridge VillageSuperhost
Accommodates: 5
Top guest reviews
Host:
the hosts were very helpful and attentivethe hosts were very friendly and extremely communicative if we had any questions during our stayRead more reviewsAmenities & Room:
the wifi was strong enough for streaming and workingthe house was super comfortable and had everything we needed
3. Lavish home with resort-like facilities; Barnstable (from USD 2681)
Enjoy your own private resort when you book this lavish property that features all the amenities of a 5-star hotel. For those seeking an active retreat, it offers various exercise and sports equipment plus a captivating swimming pool and hot tub to keep you engaged and energized.
The bedroom offers a tranquil sanctuary with extra pillows and blankets, complemented by room-darkening shades that ensure a peaceful slumber. Hook up to the WiFi and take advantage of the dedicated workspace for any work or study requirements. Create sumptuous meals in the kitchen. For outdoor enthusiasts, a private outdoor kitchen and grill are available for hosting an alfresco dinner.
Barnstable, Massachusetts, United States
151.07 km (93.9 mi) from Old Sturbridge VillageAccommodates: 10
Top guest reviews
Host:
rafael was an excellent host who was easy to communicate withrafael was a gracious host and easy to communicate withthe hosts were super easy to communicate with and were sweet and welcomingLocation:
location felt safe and was a close drive to public beachit’s a nice location convenient to area beaches attractions etcgreat place for our family to spend time togetheri would definitely book this place again for our family vacationCleanliness:
the house was very clean and had plenty of linensbathrooms are small but modern and cleanall in all it was a very clean house and perfect for our familythis is a good place for kids - the pool is salt water clean and warmthe home was very clean and spaciousRead more reviewsAmenities & Room:
the pool is beautiful and we definitely enjoyed the beach volleyball basketball courts and playground
4. Beautifully renovated home next to Monument Mountain; Great Barrington (from USD 1041)
Escape to this home with a heated saltwater pool for a perfect blend of luxury, comfort, and convenience. It is located right next to Monument Mountain, which offers breathtaking views and plenty of hiking opportunities.
Families are warmly welcomed in this newly renovated home, with amenities catering especially to the little ones, such as a crib, children’s books, and toys. A high chair and children’s dinnerware ensure that mealtime is a breeze. A baby monitor is available for added peace of mind, and board games offer fun for the whole family. Fitness enthusiasts will appreciate the private gym in the building. Parking is free on the premises, and for guests arriving in electric vehicles, there’s an EV charger for your convenience.
Great Barrington, Massachusetts, United States
102.93 km (64.0 mi) from Old Sturbridge VillageAccommodates: 8
Top guest reviews
Host:
the hosts were fantastic and accommodated our needsthe hosts were very helpful and communicative toothe hosts answered all our questions promptly and gave clear directions on how to use everythingthe hosts were quick to respond and so graciousthe hosts prem and mary were very kind and welcomingLocation:
house is also located close to great barrington town which has many cute restaurants and shopsit is super close to ski butternut amazing hikes and the lovely shops & restaurants of great barringtonthe location is unbeatable and we loved relaxing in their poolall in all a roomy elegant family friendly house in a perfect location in the berkshiresbeautiful house cozy home great location exactly as describedCleanliness:
everything about this place feels luxurious clean and modernthe place is so spotless bright and freshit was very clean and had everything we needed to enjoy the weekendthis place was fantastic it was really clean and the layout is greatthe house is spacious beautiful and cleanRead more reviewsAmenities & Room:
the house is gorgeous; from the furniture to the light fixtures to the bathroom tiles everything was beautifulspeaking of work - wifi was also greatthe rooms were large and roomy perfect for families with small childrenthe house was filled with light really comfortable beautifully decorated and cleanthe pool was luxurious with beautiful landscaping
5. Beautiful home with indoor heated pool; West Stockbridge (from USD 3969)
Picturesque at every angle, this property in Berkshires features views of the mountains that create a breathtaking backdrop to an extraordinary stay. In addition to its tasteful interior, this rental boasts central air conditioning that keeps the space comfortably cool during warm summer months, while a gas fireplace adds a touch of warmth and ambiance during cooler evenings.
The heart of any luxurious vacation is a well-equipped kitchen, and this home does not disappoint with complete appliances including a refrigerator, stove, dishwasher, and more. Additional amenities such as wine glasses and barbecue utensils further elevate the culinary experience. In the evening, you can hang around the fire pit, or enjoy a meal in the outdoor dining area.
West Stockbridge, Massachusetts, United States
110.26 km (68.6 mi) from Old Sturbridge VillageAccommodates: 11
Top guest reviews
Host:
the house & host were wonderfulhost is easy to communicate and quick at responding messagesshana is so communicative and friendly; doesn’t seem annoyed at all to be reached out toshana was an amazing host and this is a breath-takingly beautiful home the pictures do not do it justiceLocation:
great house in a great locationa wonderful house -- beautiful locationwould definitely choose this location for a weekend stay in the berkshiresgorgeous location comfortable and cleanvery easy communication with host and in a great berkshires locationCleanliness:
the place was clean and the beds were comfortableeverything was clean and in order upon arrivalwe had a wonderful stay everything was very clean and well-maintainedcheck in was a breeze with neat and clean interiorthe house is clean spacious and well appointed with every amenity includedRead more reviewsAmenities & Room:
the heated pool was greatreally lovely house with incredible views on great piece of property comfortable for 3 familiesthe view from the living/dining room is specialwe absolutely loved our stay the view from the living room is breath-takinghouse has a great kitchen lots of sleeping options and the kids enjoyed the small pool
6. Casa Mia; New Marlborough (from USD 2472)
A comfortable space for as many as 15 guests, Casa Mia is an inviting getaway for everyone – including your fur babies. Indulge in the luxury of a heated outdoor pool, open 24 hours and available seasonally. Turn up the heat further in the private hot tub or sauna.
For entertainment, hang out in the living area with a cable TV or challenge your companions to a game of ping pong. The home includes a split-type ductless air conditioner, ensuring a pleasant temperature indoors. During colder months, you can cozy up by the wood-burning fireplace. The well-stocked kitchen features a microwave, a gas stove, and an array of cooking basics. Enjoy the convenience of the kettle, coffee maker, and toaster to kickstart a productive day.
New Marlborough, Massachusetts, United States
95.2 km (59.2 mi) from Old Sturbridge VillageAccommodates: 14
Top guest reviews
Host:
easy check-in with the hostLocation:
great location less than 15 minutes from downtown great barringtonit was perfect great house and great location please letRead more reviewsAmenities & Room:
amazing home has everything you need from spacious living area to game room and tons of other amenitiesthis is a fantastic house incredibly comfortable for a big family of all agesabsolutely wonderful house charm practical layout gorgeous pool and an accurate website description
7. Farmhouse with outdoor kitchen and game pavilion; Wareham (from USD 3187)
Situated on a saltwater inlet in Buzzards Bay, this waterfront home with gorgeous views is an upscale vacation destination on its own and is not your typical farmhouse.
Thoughtfully decorated and lavishly furnished, the home is designed with the comfort of the whole family in mind. A high chair, baby bath, and children’s dinnerware cater to the needs of young guests. Safety is paramount, and the property provides window guards and outlet covers, ensuring peace of mind for parents. Prepare meals for everyone while taking in the sights and smells of the surroundings using the outdoor gourmet kitchen. Take a dip in the outdoor pool, which can be heated for a fee, or play around in the game pavilion to unwind.
Wareham, Massachusetts, United States
121.74 km (75.7 mi) from Old Sturbridge VillageAccommodates: 10
Top guest reviews
Host:
sue and her husband were wonderful hosts and very responsive whenever we had questionsthe kids even made s’mores over the fire host is also very responsive and helpful to our needssue was very responsive and kindeverything about this house is perfect from the host sue to all the accommodationsthe host thought of all the little things like floats helmets life jackets etcLocation:
the home and location allows you to completely relaxCleanliness:
sparkling clean beds were very comfortablethe house was clean and as expectedthe house is super clean and updatedthe house was spotlessly clean and extremely well equippedhouse was clean and sue was very communicative and very helpfulRead more reviewsAmenities & Room:
we enjoyed the pool and the view of the waterwe enjoyed the pool and beautiful view from the house and yardour toddlers loved the library nook and all the pool toysthe pool was great and heatedthe view is gorgeous and the pool is perfect for floating on lazy afternoons
8. Sesuit Harbor Hideaway; East Dennis (from USD 419)
This 2,428-sq.-ft. (225.57-sq-m) home in Cape Cod features exceptional leisure facilities including a seasonal swimming pool and a hot tub. Unwind in the spacious living area equipped with a cable TV. Stay cozy year-round with the air conditioning and heating options. On chilly evenings, bask in the warm glow of the indoor fireplace.
You can prepare gourmet meals in the kitchen, equipped with a refrigerator, microwave, and dishwasher for effortless cleanup. Connect to the WiFi and make use of the dedicated workspace to get your projects done. Smoke and carbon monoxide alarms, a fire extinguisher, and a first aid kit are provided for your peace of mind.
East Dennis, Massachusetts, United States
165.36 km (102.8 mi) from Old Sturbridge VillageAccommodates: 10
Top guest reviews
Location:
great house in perfect dennis locationgreat house within walking distance to many spots in dennisgreat spot great location and very accommodatingloved it the house and location is greatbeautiful place to stay close to everything you would needCleanliness:
excellent this place was very clean and cozy also great gamessuper clean and pictures accurately represent homeclean accommodating and great communication from host would recommendgreat place well maintained and cleanthe space was big and clean and the hot tub was a great featureRead more reviewsAmenities & Room:
overall very nice place and comfortable stay
9. Spacious family retreat minutes away from winery; Westport (from USD 685)
Are you looking for a vacation rental that exudes exclusivity yet is still near all the conveniences and key attractions? Look no further than this luxurious home, where you’ll have 4,000 sq. ft. (371.61 sq m) of space for your big family or group while being minutes away from the area’s best attractions including the beach, winery, and various shops.
This family-friendly space caters to guests of all ages. Children will find delight in the selection of books, toys, and children’s dinnerware. Gather everyone for some quality time with the assortment of board games available here. You can lounge on the private deck or gather around the fire pit to keep cozy. The outdoor furniture and dining area make the area ideal for alfresco meals.
Westport, Massachusetts, United States
97.25 km (60.5 mi) from Old Sturbridge VillageAccommodates: 8
Top guest reviews
Host:
fulfilled all our needs and questions very helpfulCleanliness:
the house was beautiful and cleanit's big and clean and has a lot of space for people and activitiesRead more reviewsAmenities & Room:
everything was comfortable and we had a nice stay
10. Treetops; Egremont (from USD 1800)
Feel like absolute royalty when you book this chalet-style home – adorably named Treetops for its wonderful views – which sits on a gorgeous 30-acre (12.14-hectare) property. Nestled right next to a private pond, this waterfront home features an indoor heated pool along with a host of luxurious amenities such as a hot tub and sauna.
Looking for some entertainment? Kick back in the living area and enjoy a movie night on the high-definition TV equipped with popular streaming services. Maintaining the perfect temperature is effortless, thanks to the split-type ductless air conditioner, cozy wood-burning fireplace, and heating systems. Food enthusiasts will appreciate the well-equipped kitchen, complete with a refrigerator, stove, and dishwasher. For those seeking an extended escape, long-term stays of 28 days or more are welcome.
Egremont, Massachusetts, United States
108.02 km (67.2 mi) from Old Sturbridge VillageAccommodates: 12
Top guest reviews
Host:
our house liason was very responsive and kind when we had questionswere very communicative and helpful in dealing with plowing when it snowedCleanliness:
spacious stylish clean and welcomingthe house was clean spacious and had an incredible amount to do for kidsRead more reviewsAmenities & Room:
beautiful home and the indoor pool is amazingwe had a comfortable and enjoyable stayit's a good space with a big kitchen and comfortable sleeping areasall in all a great recommendation but perhaps a little too pricey for the number of bathroomsthe swimming pool and hot tub were terrific
Answer to the beckoning of Massachusetts’ diverse attractions
Massachusetts offers a distinct character in each of its major regions, from the bustling urban energy of Boston to the serene coastal beauty of Cape Cod. Make your stay extra special by booking one of the above top luxury Airbnbs in Massachusetts, USA.
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