Holiday rentals in Great Barrington

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Popular amenities for Great Barrington holiday rentals

Stay near Great Barrington's top sights

Guido's Fresh Marketplace248 locals recommend
The Prairie Whale203 locals recommend
Baba Louie's Sourdough Pizza121 locals recommend
Monument Mountain Reservation112 locals recommend
Mahaiwe Performing Arts Center102 locals recommend
Bizen Gourmet Japanese Restaurant and Sushi Bar101 locals recommend

Other great holiday rentals in Great Barrington

Top guest favourite
Home in Athens
5 out of 5 average rating, 38 reviews

Perfect home for a getaway from NYC

ScottRating, 5 stars3 weeks ago
Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!
Top guest favourite
Home in Hillsdale
5 out of 5 average rating, 56 reviews

Lakefront close to ski & shopping

KathyRating, 5 stars2 months ago
A beautiful home and the views were breathtaking on the lake. Although, it was frozen. All the amenities we needed and more. Close to skiing and tubing. Owner Sara was very attentive to respond quickly. We just wanted a getaway place for a family weekend. The road was narrow and very icy. Would go back but not in the winter. Summer and the Fall I think would be best. Lots more things to do in the nicer weather months. Thank you Sara for your hospitality.
Top guest favourite
Home in Millerton
4.97 out of 5 average rating, 181 reviews

Vacation Home In Millerton

SarahRating, 5 stars1 week ago
We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!
Top guest favourite
Home in Charlemont
4.95 out of 5 average rating, 56 reviews

Tall Pines Rental

GeorgiaRating, 5 stars2 weeks ago
It's hands down one of the best AirBnBs in the area! I've stayed at three different homes in the Charlemont area over the past three years, and this is by far the best. The home is in a perfect location near town, yet still feels private and secluded. It had everything we needed to make our stay seamless (keyless entry, TV, heat, all the kitchen utensils you could think of, extra amenities in the bathroom, etc.) They are also incredibly welcoming to pets - they even have extra dog bowls and a dog bed! If you're looking for a beautiful space that feels like home (with a reasonable price), this is it!
Guest favourite
Chalet in Athens
4.86 out of 5 average rating, 49 reviews

Large & Sunny Lakefront Home-kayaks/fire pit/games

KatieRating, 5 stars4 days ago
This was such a relaxing home to spend a celebratory weekend in! We had a great time at Adnan's home over the weekend. The setting is so peaceful, right on the water and we enjoyed the fire pit one evening. The space is large, with plenty of room for all. The house is a little bit dated, but with that said, it had everything we needed for a lake-weekend! On top of that, Adnan could not have been more accommodating and responsive.
Top guest favourite
Home in Lanesborough
5 out of 5 average rating, 16 reviews

Berkshire Mountain House

DestinyRating, 5 stars1 week ago
This Airbnb exceeded our expectations! The house is spacious and super family friendly (also great for just adults). We loved the Airbnb so much that we only left the house once. Our hosts were very attentive and accommodating. I would recommend to anyone who is looking for a getaway in the Berkshires no matter the season.
Guest favourite
Home in Athens
4.91 out of 5 average rating, 11 reviews

Cozy Catskill Getaway by Hudson

PaulaRating, 5 stars4 days ago
Lovely and cozy house, perfect for families! We will be back with nicer weather! Perfect house to make you feel at home with a lot of games to keep everybody entertained
Top guest favourite
Home in Averill Park
4.96 out of 5 average rating, 159 reviews

Cozy, peaceful lake house close to Jiminy Peak

JenRating, 5 stars1 month ago
We loved our late winter stay on the lake - it was very peaceful and we had some great bird-watching opportunities. The art and special objects in the house made for a very cozy and beautiful environment. Overall, it was very comfortable and we would definitely stay again.

Quick stats about holiday rentals in Great Barrington

  • Total rentals

    240 properties

  • Total number of reviews

    10K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

Destinations to explore