Top 10 Airbnb Vacation Rentals In Stockbridge, Massachusetts - Updated 2021

airbnb stockbridge ma

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.

1. Rustic cabin with modern appliances (from USD 403)

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.

NEW Stockbridge Cabin - A quick stroll to the lake
Stockbridge, Massachusetts, United States
38 reviews
Entire cabin 5 Beds 3 Bedrooms 1 Bathrooms
Top guest reviews
Amenities & Room:
quiet street warm and cozy feeling
place was sparkling clean and very newly renovated
great getaway from nyc and exactly as advertised incredibly clean and cozy
the house was well appointed and clean upon our arrival
all the beds are so comfortable and the place was sparkly clean
it was clean and comfortable - we certainly recommend
elle is a great host who was always responsive
elle is a great host and very responsive
finally elle was a great host who communicated very well via airbnb messages
elle is very communicative and helpful
elle was responsive accommodating and available which was much appreciated
the proximity to town is excellent and loved the ability to walk to the beach
walk was easy to stockbridge bowl
location was perfect with proximity to the stockbridge town beach and tanglewood
great location to access stockbridge and lenox and hopefully in the future tanglewood and other cultural locations
there is so much to do in the berkshires and this is great location overall
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2. Peaceful cottage surrounded by lush forest (from USD 261)

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.

Romantic, Chic Interlaken Cottage Stockbridge
Stockbridge, Massachusetts, United States
188 reviews
Entire cottage 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
we loved our stay at this cozy and beautiful cottage
we found her local tips to be helpful in finding a breakfast spot coffee and grocery shopping
other nice touches: wonderful screened-in porch/ (website hidden by airbnb) cozy
it was very clean and neat
it was sparkling clean and very bright
the cottage is clean cozy and beautifully decorated
very clean well decorated with lots of personal touches
very clean and well- appointed cottage
host very responsive
jess is an excellent host
jess was an excellent host to my parents
jess is a fantastic host who covered everything
jess is a responsive and thoughtful host
perfect location in the berkshires
great location and so peaceful
i loved the location a bit isolated but close enough to neighbors to feel safe
location is great near both stockbridge and the beautiful lenox
so close to tanglewood and nice restaurants as well
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3. 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.

Cozy cottage by the brook
Stockbridge, Massachusetts, United States
185 reviews
Entire house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the air conditioner and shower worked very well
cozy cottage is absolutely lovely
working wifi and flowers from host an added welcoming bonus
the bathroom is gorgeous the bed very comfortable and the fresh flowers were a nice touch
it was very cozy clean and the amenities were modern despite a rustic overall feel
clean and bright
very clean space and lovely bathroom
everything was very clean tidy and the bathroom was spotless with modern appliances
great spot really clean and comfortable
new and clean
easy check in and quick responses from host
great host and place to stay
susan was a gracious host
susan and will were gracious hosts
susan and will were amazing hosts
wonderful location within walking distance to stockbridge
stylish spot great location too
nice location to the surrounding villages
close to downtown stockbridge and a quick drive to great barrington
very cozy and cute inside and close to downtown stockbridge
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4. Cabin close to the lake (from USD 312)

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.

NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!
Stockbridge, Massachusetts, United States
13 reviews
Entire cabin 4 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
craig was a great host
the host replies very fast and welcome
very cute cottage with a great location right across from the lake and public beach
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5. Luxurious vintage home (from USD 250)

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.

Artist Cottage on the Lake
Stockbridge, Massachusetts, United States
3 reviews
Entire cottage 2 Beds 3 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
three adults in family very comfortable in the space
very nice cabin in great location near stockbridge bowl
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6. House in the woods near walking and biking trails (from USD 464)

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.

ESCAPE to STOCKBRIDGE Avail August 1-14|Berkshires
Stockbridge, Massachusetts, United States
68 reviews
Entire house 5 Beds 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
loved the outside space with the grill tables and firepit
beds were super comfortable
the house is stunning—extremely well decorated and comfortable for a large gathering
clean and well maintained
clean and tidy home
the house was very clean and beautifully decorated
house was well-equipped and clean
tim’s place was exactly as pictured: clean very spacious and peaceful
tim was an amazing host
tim was an amazing host
our host was flexible and extremely responsive
people were so nice and friendly
thank you to the hosts for all the thoughtful touches
location is great close to both stockbridge and great barrington
great house in a perfect location
great location - close to stockbridge and lenox
it’s situated in the perfect location close to everything that makes berkshires the perfect destination
close to tanglewood lenox great barrington
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7. Vacation home close to the lake (from USD 607)

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.

5 Star Berkshire Vacation Home, Walk To Lake Beach
Stockbridge, Massachusetts, United States
15 reviews
Entire house 5 Beds 5 Bedrooms 3 Bathrooms
Top guest reviews
henry's house is beautiful comfortable spotlessly clean and well appointed
his home was very spacious clean and well furnished
the host henry was extremely quick with responses which always is a huge plus
henry is a terrific host
it's location is great
all around a wonderful and comfortable place to stay we will be back
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8. Huge home with modern amenities (from USD 602)

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.

"Too Good" AKA 2 Goodrich St.
Stockbridge, Massachusetts, United States
46 reviews
Entire house 6 Beds 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
we loved the house the kitchen the deck the fire pit and reading areas
lovely home with spacious rooms and lots of natural light
the house is beautiful spacious comfortable and hip and the property is well-kempt serene and gorgeous
the house was very clean and well stocked
the house was so clean and nice and exactly how it was described
it was very spacious bright and clean
the house was clean and updated with plenty of room and spaces for kids and adults
ten guests stayed at the house and found it to be incredibly spacious clean and accommodating
the host was easily reachable and responsive
he was a fabulous and very responsive host
teva was a wonderful and generous host
great hosts welcomed our group who was there for a nearby wedding
responded to a call or text right away and was a very nice host
we loved this house the location couldn't be better
fantastic hikes super close by at ice fells and monument mountain
this is a very comfortable home in a great location - 10 min from great barrington
the location is excellent - close enough to many things to do and see
the house is in a perfect location and has tons of areas for a large crowd
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9. Classic home with private deck (from USD 319)

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.

Tranquil 3BR Stockbridge House w/Private Deck
Stockbridge, Massachusetts, United States
20 reviews
Entire house 5 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the decor furnishings & beds were extremely comfortable
the hosts were responded promptly to questions and were helpful
check-in system & communication with hosts was efficient & easy
the location of this house is really perfect
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10. Newly renovated historic home (from USD 275)

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.

Renovated Historic Home in the Berkshires
Stockbridge, Massachusetts, United States
36 reviews
Entire house 3 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
immaculate beautiful and very comfortable space had everything we needed
modern and comfortable with all the right touches
very nicely renovated and very clean
the house is impeccably clean well equipped and highly organized
the house was beautifully renovated and very clean
we had a truly wonderful stay at this beautiful house everything was nicely appointed and sparkling clean
what a perfect weekend house it was extremely clean and comfortable tucked away on a quiet street
the host was easy to communicate with and the check in instructions were simple and seamless
alexandra was a communicative and responsive host
the owners have gone above and beyond to ensure you have a comfortable stay
the location is great so central to everything we wanted to do and more
location on a quiet street is convenient to several area attractions
great location right near norman rockwell museum and close to area restaurants
it was very quiet yet still close to many berkshires attractions
and we had a great time walking over to chesterwood and exploring the nearby forest
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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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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