Looking for a place in Massachusetts where you can please your desire for outdoor adventures in the middle of nature? There is just a perfect town for you. Make your way to Great Barrington. Enjoy skiing at either Ski Butternut Tubing Center or Catamount Mountain Resort. The next day, try hiking and outdoor recreation at Monument Mountain Reservation that boasts lush plantation and majestic mountains. Those who are into camping can enjoy a beautiful time at Beartown State Forest. For adrenaline pumping activities such as zip lining and other aerial adventures, you should stop by Catamount Aerial Adventure Park. Wondering where to stay? Read on and you will learn about the best Airbnb vacation rentals in Great Barrington, Massachusetts.
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. Victorian-style apartment with a back patio (from USD 214)
Have a pleasant stay at this apartment that looks like a mini Victorian building. Situated only a few minutes away from Butternut Ski area, the apartment can accommodate four guests that can comfortably sleep in its two spacious bedrooms. You are invited to relax and unwind at the back patio with a cup of coffee in your hand. There is a kitchen with a gas stove to help you prepare delicious dinner or breakfast.
Top guest reviews
Amenities & Room:
bedroom a/c was necessary and kept it nice and cool for sleepingvery comfortable home with stylish furnishingsbeautifully furnished and comfortable place with all needed amenitiesi slept so well couch in the main room is also super comfy for hanging out3 tvs in the house great bathroomCleanliness:
great place new appliances clean plentiful towels and very clean and comfortablethis house is very clean and comfortableit was very clean and check instructions were clearthe house was clean with towels sheets soaps etcgreat clean central home baseHost:
our host was wonderfulour host was very responsive and quick to answer questionslynn was a great hostlynne was a great hostlynne was a great host who was so responsive to any and all questions we hadRead more reviewsLocation:
the location was perfect — very close to downtownlocation is great toothe location is ideal with an easy 15 minute walk to downtown gbthe location was great near the centeramazing house in an amazing location
2. Enchanting old cottage with an outdoor hot tub (from USD 175)
Old buildings are always enchanting and to experience an enchanting stay in Great Barrington, spend a couple of days at this 100-year-old cottage. Nestled at the Foot of Monument Mountain, the cottage features one bedroom and two bathrooms, making it ideal for couples who are looking for a hideaway or solo travelers. Indulge in a refreshing outdoor hot tub whenever you feel like relaxing; it’s open all year round. There is a fireplace to help create a romantic vibe in the evening. Other facilities offered include a wood stove and a large-screen television.
Top guest reviews
Amenities & Room:
the cottage is very charming- so cozy and comfortablethe house has great wifi and a well equipped kitchenthe entire cottage is lovely and dreamy but the upstairs bathroom is phenomenalthe upstairs bath and bathroom is a dream come truethe cottage was perfect for our weekend getaway comfortable quiet and close to all the area attractionsCleanliness:
the space was exceptionally clean and organizedvery quiet and cleanthe place itself was super clean and perfect for two peoplethe cottage was very clean and nicely presentedthis place is so special it is clean and quiet and all the details make it feel luxuriousHost:
the hosts are kind and generous and went out of their way to make us feel comfortablejanet and doug were great hosts -- very responsive to all our questions and needshighly recommended douglas and janet are amazing hostsjanet was kind in responding to any questions i had and giving suggestions on places to visitthe hosts welcome the use of their art studio which will make your trip exceptionally uniqueRead more reviewsLocation:
it was a wonderful accommodation close to everythingreally a perfect location to explore the berkshiresa fantastic spot great location cozy spacereally relaxing and peaceful locationthe cottage was perfectly situated between great barrington and stockbridge a quick 15 drive to either location
3. French manor house with all luxuries possible (from USD 925)
Welcome to this elegant French manor house and indulge in all luxuries possible, where everyday is going to be just fun. First of all, the house is equipped with four bedrooms and four bathrooms to accommodate twelve people in total. So, bring as many people as you can to explore Great Barrington with you. Then, the house boasts a swimming pool and a tennis court to keep you active at all times. Finally, you are going to love its formal living and dining rooms along with a fireplace and exquisite Gauguin Bar.
Top guest reviews
Amenities & Room:
the wifi was a great and sincerely appreciated the netflix on the tvswe spent our entire stay swimming in the perfectly heated poolthe kitchen is beautiful and was such a treat to cook inthe beds were extremely comfortable as were the couches in the living roomCleanliness:
what a beautiful house especially the swimming pool is very cleanwe loved the stylish decor spaciousness and cleanliness of the homeRead more reviewsLocation:
manor lane is an amazing place to staygreat location and 5-10 minutes from the center of great barrington and ski butternutan ideal place for family get togethersbeautiful and spacious home close to town - abigail was extremely gracious and quick to respondthe house is also close to two ski mountain which we also enjoyed since we visited in january
4. Massive house overlooking the tree-topped mountains (from USD 318)
What happens when you are surrounded by the tree-topped mountains, rolling hills and old historic town buildings? You will want to stay in a place like this forever. That is why you need to book this massive house that features eight comfortable beds for fourteen people. The house is equipped with everything you may need for a comfortable stay, from a well equipped kitchen and a living room with a television and a fireplace to a huge deck with rocking chairs and modern bathrooms.
Top guest reviews
Read more reviewsHost:
host was very responsivelucas thought of everything and was a very gracious host with a beautiful home
5. Quaint cottage with a private garden (from USD 130)
Located within a quick drive from downtown Great Barrington, this quaint cottage makes an excellent place of stay for couples or solo adventurers. As soon as you wake up, be headed to the porch to enjoy a peaceful atmosphere and fresh morning air. Then, after sipping your coffee, take a pleasant walk in the private garden to treat your eyes and mind. Other facilities provided include wood stove, basic cookware, and sheets and towels.
Top guest reviews
Amenities & Room:
comfortable bed with a beautiful viewspeaking of sleeping the bed has an incredibly comfortable mattress and lots of pillowswe stayed warm in this adorable cozy cottage during our visitno tv (a nice change) but great wifithe bed was very comfortable with lots of blankets and pillowsCleanliness:
) and was clean upon arrivalvery quiet and clean spacewell equipped clean and comfythe cabin was clean and warm when we arrivedthe cabin was clean with fresh linens towels soap and shampooHost:
seamus was an excellent hosthost is very responsivehost is awesome and thoughtfulseamus was very communicative and provided great recommendations for nearby hikesseamus was very responsive to our requests and messages before and during our stayRead more reviewsLocation:
great location very cozya cute cabin in a very quiet location perfect location near great barringtonlocation is great very close to town and hiking trailswonderful cozy cabin perfectly located on a quiet wooded street but close to downtown great barringtonyet very close to the adorable town of great barrington
6. Old red barn located between Butternut and Catamount ski resorts (from USD 150)
Welcome to this old red barn that guarantees a joyful stay throughout. Featuring a strategic location between the two popular ski resorts, the barn boasts pine floors, cathedral ceiling and exposed beams in its bedroom. Sit back and recharge in the contemporary living space with an open floor plan. Whip up a delicious breakfast in the fully equipped kitchen. Relax in the outdoor area in the evening and make use of the gas fire pit and private deck.
Top guest reviews
Amenities & Room:
the barn is extremely cozy and comfortable with a beautiful vieweverything was perfectly clean functional and comfortable especially the couch and the bedthe space is decorated so nicely and the bed was incredibly comfortablethe space was serene cozy beautifully decorated and had everything we needed for a relaxing staygorgeous barn with a very comfortable queen size bed with lots of pillow optionsCleanliness:
clean spacious and comfortableeverything is clean and very well doneeverything was clean and set up for our arrivalthe place was very clean and check in was very easyfabulous and clean space; good findHost:
julie was a wonderful host and quick to answer any questionsjulie was also very welcoming and responsivejulie is a great host and made us feel very comfortable from the startsuper host super placejulie was a very generous attentive yet unobtrusive hostRead more reviewsLocation:
great place close to downtown main street but not too closeit’s in a beautiful and quiet location yet still very close to townsuch a great location very near to great barrington in a rural peaceful settingthe barn is in a convenient location about 5 minutes from downtown great barringtonclose to town yet private and relaxing
7. Secluded chalet with exposed wooden beams and ceilings (from USD 278)
If you are looking for a sweet escape where no one will bother you, you should book this secluded chalet right away. There will only be lush views all around that can be enjoyed through endless windows. Wake up to the sound of the birds calling and enjoy a cup of coffee in the living area. Up to eight people can spend quality time at this chalet that features three bedrooms and two bathrooms.
Top guest reviews
Cleanliness:
ive never been so inundated with cozy blankets very clean and homeya beautiful spacious chalet with lots of windows airy in a private beautiful settingthe zen chalet is super comfortable clean quiet and close to great barrington and butternutHost:
pamela was very helpful to us with tipspam is a terrific host and responds immediately to any concernsRead more reviewsLocation:
private but so close to the town of great barringtonit was so close to towns and ski butternut and made for a wonderful family vacationsuch a nice place to getaway cozy and relaxing very nice decoration
8. Modest flat located in the beautiful Berkshires
Small families of three or couples who are planning to have a quiet stay in Great Barrington may want to consider booking this modest flat that is set in the Berkshires. The flat comes with one bedroom and one bathroom. In addition, there’s a television and a fully equipped kitchen that guests can take advantage of.
Great Barrington, Massachusetts, United States
12.21 km (7.6 mi) from Norman Rockwell MuseumSuperhost
Accommodates: 3
Top guest reviews
Amenities & Room:
good wifi and excellent air conditioningvery good aircon and the wifi worked well during our staythe king bed was very comfortable and we enjoyed breakfast on the patioand we enjoyed the beautiful peonies on the tablelarge and clean apartment- fit our needs for a visit to the berkshire school the next morningCleanliness:
everything was clean and communication was easyquiet clean and comfortablemarc’s place was clean and very comfortableprivate clean and comfortablethe apt was very clean with the kitchen equipped nicely bathroom with towels and other needsHost:
communicative & friendly hoststhe owners were quick to respond to any questions and were very welcomingshe was very friendly and helpfulour hosts were excellent as wellamanda was a perfect host accommodating our late arrival and responding quickly to every messageRead more reviewsLocation:
the location was perfect very close to downtownthe location is in close proximity to the downtown area of great barringtonclose to town and shopping as well as close to many wonderful hiking spotslocation was convenient to our hiking destinations and to very cute nearby townsgreat location and plenty of space
9. Cozy apartment in the heart of Great Barrington
Relax and recharge in this apartment that promises a cozy stay right in the heart of Great Barrington. The apartment features two bedrooms and two bathrooms. As a guest of this apartment, you will also be granted access to a living area that comes with comfortable sofas and couches and a fully equipped kitchen for home-made cooking, among others. There are plenty of windows that will bring in sufficient sunlight to keep you energized throughout the day.
Great Barrington, Massachusetts, United States
11.08 km (6.9 mi) from Norman Rockwell MuseumTop guest reviews
Amenities & Room:
the house is perfect for two couples with the two bathrooms and two bedroomsthere is even an essential oil diffuser in the living room for some soothing aroma therapyCleanliness:
clean and very quietclean bright and welcomingthe house is spotlessly clean and nicely decoratedclean beautiful elegant and thoughtfulthe house was clean well stocked and aesthetically beautifulHost:
erika is a wonderful host5 stars across the board great place excellent and generous hosterika is very responsive and welcomingRead more reviewsLocation:
the location is greatit’s located on a really cute street across from a park and perfect walking distance to townlovely place near downtown great barringtonthe house was a great location in gbwonderful hostess great location and a good value
10. Comfortable house with a large swimming pool
Situated in a quiet neighborhood yet not far from major attractions and amenities such as restaurants and shopping centers, this comfortable house is ideal for eight people that can enjoy a good night’s rest in the four big bedrooms provided. After an exciting day of adventure in the town, welcome back to the house and find yourself soaking in the large swimming pool. Or, treat yourself with a glass of wine and savor it in front of the burning fireplace.
Great Barrington, Massachusetts, United States
11.46 km (7.2 mi) from Norman Rockwell MuseumAccommodates: 8
Top guest reviews
Amenities & Room:
the backyard was wonderful - large yard beautiful pool area great patio with tables and grillfrom cheese knives to champagne stoppers the kitchen had everything we needed for a relaxing indulgent weekendthis is a fabulous home beautifully decorated extremely comfortable loaded with amenities and very cleanit was perfect for a weekend getaway to relax by the pool and bbq on the deckthe kitchen is well-stocked and has the perfect layout for entertainingCleanliness:
and we found the place quite clean upon arrivalit is very clean well decorated and updated from end to endthe house is very well equipped and cleanrobin's house is absolutely perfect: cozy clean comfortablethe house itself is well maintained clean and filled with artistic touchesHost:
robin was an amazing hostowners always available and responsivewonderful hosts and a comfortable spacious homei can’t thank robin and dai enough for being such great hostsrobin was an incredible host and made everything very easy for usRead more reviewsLocation:
the close location to great barrington and surround towns was ideal for usgreat location being very close to town but also feeling remote at the same timethe location is secluded yet a short drive to lots of interesting placesthe location is fantastic- so close to town and as well as hikes lakes and waterfallsthe house & location are beautiful
Outdoor nature-based retreats in Great Barrington
So, what are you waiting for? Instead of spending days at home, it would be much better to explore a new place. Incredible nature retreats with amazing views and super fun outdoor adventures await you in Great Barrington. Just be sure that you have secured your favorite Airbnb vacation rental for a comfortable vacation.
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