Stockbridge is an attractive town with many landmarks, beautiful mansions, and impressive cottages. You will learn a lot about Stockbridge’s past as you take a trip to its historic and cultural sites. Reconnect with nature as you walk on numerous trails around the area. Satisfy your hunger by choosing among the top-rated restaurants and delis. If you are looking for unique souvenir items to bring home, Stockbridge shops have them all. A comfortable place to stay is important to fully enjoy your vacation, so check out the following list of Airbnb vacation rentals in Stockbridge, Massachusetts, and choose which rental fits you best.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 09, 2024.
1. Cozy cottage in Stockbridge (from USD 157)
This cute cottage looks unbelievably spacious because of the high ceiling and bright interior. The living area has a comfy couch facing a brick fireplace that separates the bedroom and the living area. The snug bedroom looks bright, thanks to the natural light flooding in from the glass windows and patio door. The kitchen has all the appliances you might need. The back deck has an outdoor bbq and a seating area with a table where you can see the relaxing view of the trees and the brook, and breathe in the fresh morning air. Location wise, it is close to town and walking trails. Wifi, cable TV, air conditioning, heating, essentials, and free parking are also provided.
Top guest reviews
Amenities & Room:
the air conditioner and shower worked very wellcozy cottage is absolutely lovelyworking wifi and flowers from host an added welcoming bonusthe bathroom is gorgeous the bed very comfortable and the fresh flowers were a nice touchit was very cozy clean and the amenities were modern despite a rustic overall feelCleanliness:
clean and brightvery clean space and lovely bathroomeverything was very clean tidy and the bathroom was spotless with modern appliancesgreat spot really clean and comfortablenew and cleanHost:
easy check in and quick responses from hostgreat host and place to staysusan was a gracious hostsusan and will were gracious hostssusan and will were amazing hostsRead more reviewsLocation:
wonderful location within walking distance to stockbridgestylish spot great location toonice location to the surrounding villagesclose to downtown stockbridge and a quick drive to great barringtonvery cozy and cute inside and close to downtown stockbridge
2. Cabin close to the lake (from USD 321)
White paint with gold and gray accents and little splashes of color make the interior look classy. Prepare delicious meals for everyone in the fully equipped kitchen. The bedrooms also look bright and serene, and the beds are cozy. The sunroom can be used as a bedroom for an extra guest. More so, the expansive deck is a good place to stretch out in the morning, do your yoga in the afternoon, or have a tasty bbq night. The view of the trees and hills in the distance is superb from the deck. The cottage is a few steps away from Stockbridge Town Beach. The amenities available are WiFi, a TV, air conditioning, and free parking.
Top guest reviews
Read more reviewsLocation:
very cute cottage with a great location right across from the lake and public beach
3. Huge home with modern amenities (from USD 333)
This huge house surrounded by various greeneries has a visually striking exterior and a well-tended garden. It is located close to Stockbridge, Great Barrington, and nature trails. Downstairs, you will find a sitting area, a kitchen, which is newly furnished with modern appliances, and a bright dining area which opens up to the porch. You can have quiet afternoons under the shade of the trees outside while reading a good book. BBQ dinners on the back deck are perfect on warm nights. Upstairs, you will find more sitting areas, roomy and restful bedrooms, a media room, and another porch.
Top guest reviews
Amenities & Room:
we loved the house the kitchen the deck the fire pit and reading areaslovely home with spacious rooms and lots of natural lightthe house is beautiful spacious comfortable and hip and the property is well-kempt serene and gorgeousCleanliness:
the house was very clean and well stockedthe house was so clean and nice and exactly how it was describedit was very spacious bright and cleanthe house was clean and updated with plenty of room and spaces for kids and adultsten guests stayed at the house and found it to be incredibly spacious clean and accommodatingHost:
the host was easily reachable and responsivehe was a fabulous and very responsive hostteva was a wonderful and generous hostgreat hosts welcomed our group who was there for a nearby weddingresponded to a call or text right away and was a very nice hostRead more reviewsLocation:
we loved this house the location couldn't be betterfantastic hikes super close by at ice fells and monument mountainthis is a very comfortable home in a great location - 10 min from great barringtonthe location is excellent - close enough to many things to do and seethe house is in a perfect location and has tons of areas for a large crowd
4. Classic home with private deck (from USD 255)
This beautiful classic home is only a short drive away from the center of Stockbridge. There are numerous hiking trails within the property. The décor and chosen furniture pieces give the house a retro vibe. Natural lighting illuminates every corner of the house. The kitchen is equipped with basic appliances you might need. Evenings are made warm thanks to the fireplace in the living area. The comfort of the bedrooms is unparalleled, so you will always have a good night’s sleep. Bask in the subtle morning sun in the sitting areas on the porch as you stare at the surrounding trees.
Top guest reviews
Amenities & Room:
the decor furnishings & beds were extremely comfortableHost:
the hosts were responded promptly to questions and were helpfulcheck-in system & communication with hosts was efficient & easyRead more reviewsLocation:
the location of this house is really perfect
5. Newly renovated historic home (from USD 295)
This house’s neat, minimalist interior with earthy colors is a pleasure to look at. Cooking will be the least of your worries because the kitchen is spacious and fully equipped. The living area has comfy couches and a cozy hearth to keep you warm on cold days. You will have restful nights as you sleep in the bedrooms upstairs after a day full of activities in the nearby attractions. In the mornings, it is ideal to eat your breakfast on the screened-in porch so that you can appreciate the surrounding trees, the soft morning sun, and the calming sound of the water running in the nearby stream.
Top guest reviews
Amenities & Room:
immaculate beautiful and very comfortable space had everything we neededmodern and comfortable with all the right touchesCleanliness:
very nicely renovated and very cleanthe house is impeccably clean well equipped and highly organizedthe house was beautifully renovated and very cleanwe had a truly wonderful stay at this beautiful house everything was nicely appointed and sparkling cleanwhat a perfect weekend house it was extremely clean and comfortable tucked away on a quiet streetHost:
the host was easy to communicate with and the check in instructions were simple and seamlessalexandra was a communicative and responsive hostthe owners have gone above and beyond to ensure you have a comfortable stayRead more reviewsLocation:
the location is great so central to everything we wanted to do and morelocation on a quiet street is convenient to several area attractionsgreat location right near norman rockwell museum and close to area restaurantsit was very quiet yet still close to many berkshires attractionsand we had a great time walking over to chesterwood and exploring the nearby forest
6. Luxurious vintage home
The Taggart House was built in 1850 and it was renovated to become a vacation house in 2014. It has many exquisitely-decorated rooms. The living room, great room, and dining room look elegant because of the fancy furnishings and chandeliers. The kitchen also looks lavish. The house has a conservatory overlooking the front yard, which is a big room with sofas surrounded by wide glass windows. More so, each spacious bedroom upstairs has a unique theme and an en-suite bath. Around the estate are huge trees that add to the privacy of the whole house. Amenities are WiFi, indoor fireplaces, cable TV, air conditioning, heating, children’s necessities, an outdoor bbq grill, and free parking.
Stockbridge, Massachusetts, United States
4.49 km (2.8 mi) from Norman Rockwell MuseumAccommodates: 6
Top guest reviews
Amenities & Room:
three adults in family very comfortable in the spaceRead more reviewsLocation:
very nice cabin in great location near stockbridge bowl
7. Peaceful cottage surrounded by lush forest
The carefully chosen decor makes the place look and feel homey. You can see the gas fireplace and cable TV on one side and the queen bed on the other. From the bedroom, you will access the loft which has a working desk. The kitchen is equipped with complete appliances. Beyond the kitchen is the screened living room overlooking the surrounding shrubs and trees. Moreover, Stockbridge Bowl is just adjacent to the cottage. The other amenities are wifi, air conditioning, heating, essentials, free parking, and a bbq grill on the outdoor patio.
Stockbridge, Massachusetts, United States
4.08 km (2.6 mi) from Norman Rockwell MuseumSuperhost
Accommodates: 2
Top guest reviews
Amenities & Room:
we loved our stay at this cozy and beautiful cottagewe found her local tips to be helpful in finding a breakfast spot coffee and grocery shoppingother nice touches: wonderful screened-in porch/ (website hidden by airbnb) cozyCleanliness:
it was very clean and neatit was sparkling clean and very brightthe cottage is clean cozy and beautifully decoratedvery clean well decorated with lots of personal touchesvery clean and well- appointed cottageHost:
host very responsivejess is an excellent hostjess was an excellent host to my parentsjess is a fantastic host who covered everythingjess is a responsive and thoughtful hostRead more reviewsLocation:
perfect location in the berkshiresgreat location and so peacefuli loved the location a bit isolated but close enough to neighbors to feel safelocation is great near both stockbridge and the beautiful lenoxso close to tanglewood and nice restaurants as well
8. Vacation home close to the lake
Are you planning to have a large group vacation and to bring your dog as well? Then consider booking this sublime retreat home nestled in the woods yet accessible to trails and downtown areas. Towering trees set the peaceful ambiance of the whole property. The interior of the house is tastefully decorated. The upper level contains the living room, dining area, and a large well-furnished kitchen. The lower level den with fireplace is another good area to lounge. Enjoy the view of the trees outside while you relax in the screened-in porch or the deck. The backyard is large enough for playing light sports. Wifi, cable TV, air conditioning, heating, indoor fireplaces with logs stocked outside, children’s necessities, and a lot of parking space, are also available.
Stockbridge, Massachusetts, United States
3.5 km (2.2 mi) from Norman Rockwell MuseumAccommodates: 11
Top guest reviews
Cleanliness:
henry's house is beautiful comfortable spotlessly clean and well appointedhis home was very spacious clean and well furnishedHost:
the host henry was extremely quick with responses which always is a huge plushenry is a terrific hostRead more reviewsLocation:
it's location is greatall around a wonderful and comfortable place to stay we will be back
9. Rustic cabin with modern appliances (from USD 357)
The interior of this home is a paradise. Warm lights brighten the place, highlighting the intricate woodwork in each room. There are a lot of seating areas in the living area. On a snowy night, gather up with your cabinmates in front of the hearth and sip on a cup of chocolate with marshmallows on top. Cooking will never be a problem because the kitchen is complete with modern appliances. The bedrooms are spacious and cozy. There are additional sleeping areas in the upstairs loft for large groups. From the outside patio, you can see the tall trees and green grass surrounding the house. Stockbridge Bowl is only a walking distance away.
Top guest reviews
Amenities & Room:
quiet street warm and cozy feelingCleanliness:
place was sparkling clean and very newly renovatedgreat getaway from nyc and exactly as advertised incredibly clean and cozythe house was well appointed and clean upon our arrivalall the beds are so comfortable and the place was sparkly cleanit was clean and comfortable - we certainly recommendHost:
elle is a great host who was always responsiveelle is a great host and very responsivefinally elle was a great host who communicated very well via airbnb messageselle is very communicative and helpfulelle was responsive accommodating and available which was much appreciatedRead more reviewsLocation:
the proximity to town is excellent and loved the ability to walk to the beachwalk was easy to stockbridge bowllocation was perfect with proximity to the stockbridge town beach and tanglewoodgreat location to access stockbridge and lenox and hopefully in the future tanglewood and other cultural locationsthere is so much to do in the berkshires and this is great location overall
10. House in the woods near walking and biking trails
Switch to vacation mode and enjoy the serenity of living amidst nature when you choose to stay in this gorgeous and pleasantly decorated home. Gather with your family for movie nights or board game nights in the living room. Cook a hearty breakfast for everyone in the fully equipped kitchen before you head out for an adventurous day of walking or biking on nearby trails, fishing in the river across the street, or exploring downtown Stockbridge. An outdoor bbq dinner would feel nice after a tiring day. Afterward, you can gather around the firepit while sharing stories and S'mores. Sleeping soundly will never be a problem in the very comfy beds.
Stockbridge, Massachusetts, United States
2.6 km (1.7 mi) from Norman Rockwell MuseumAccommodates: 9
Top guest reviews
Amenities & Room:
loved the outside space with the grill tables and firepitbeds were super comfortablethe house is stunning—extremely well decorated and comfortable for a large gatheringCleanliness:
clean and well maintainedclean and tidy homethe house was very clean and beautifully decoratedhouse was well-equipped and cleantim’s place was exactly as pictured: clean very spacious and peacefulHost:
tim was an amazing hosttim was an amazing hostour host was flexible and extremely responsivepeople were so nice and friendlythank you to the hosts for all the thoughtful touchesRead more reviewsLocation:
location is great close to both stockbridge and great barringtongreat house in a perfect locationgreat location - close to stockbridge and lenoxit’s situated in the perfect location close to everything that makes berkshires the perfect destinationclose to tanglewood lenox great barrington
Take a break and visit Stockbridge
Before embarking on your journey, make sure you have plenty of memory space in your phone, for unlimited photos as you roam around this quaint town. Collect memories with your loved ones as you discover excellent places to eat, stay, and relax.
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