A large stone church with a tall bell tower and arched windows.

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Our top choices for Great Barrington vacation homes

1. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 820
AED 1,260 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat

2. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (36 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 992
AED 1,502 total
includes taxes & fees
12 Aug - 13 Aug
Home in Great Barrington

3. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AED 1,605
AED 2,613 total
includes taxes & fees
1 Sep - 2 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.

4. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AED 2,079
AED 4,879 total
includes taxes & fees
13 Aug - 14 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

5. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AED 643
AED 1,169 total
includes taxes & fees
1 Sep - 2 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.

6. Berkshire House Stay: 5BR/5BA

Berkshire House Stay: 5BR/5BA
Lee
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
The price is AED 2,270
AED 4,209 total
includes taxes & fees
9 Aug - 10 Aug
Berkshire House Stay: 5BR/5BA

7. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is AED 1,091
AED 2,028 total
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature

8. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is AED 1,478
AED 2,334 total
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape

9. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AED 393
AED 1,317 total
includes taxes & fees
26 Aug - 27 Aug
Real Estate: Therapy - Lake, Laundry, Love it

10. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AED 257
AED 756 total
includes taxes & fees
9 Aug - 10 Aug
NEW RENO - Chalet-style farm loft near Tanglewood

11. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AED 1,212
AED 2,353 total
includes taxes & fees
2 Sep - 3 Sep
Treetop Hideaway in Tyringham

12. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AED 390
AED 519 total
includes taxes & fees
9 Aug - 10 Aug
All the comforts of home

13. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is AED 1,868
AED 3,206 total
includes taxes & fees
2 Sep - 3 Sep
Stylish Mid-century Modern Berkshires Cape

14. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AED 783
AED 1,659 total
includes taxes & fees
19 Aug - 20 Aug
stylish Berkshires Retreat

15. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very Good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is AED 1,190
AED 2,318 total
includes taxes & fees
19 Aug - 20 Aug
Spacious Central Berkshires Home for Groups

16. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AED 507
AED 882 total
includes taxes & fees
30 Aug - 31 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester

17. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is AED 918
AED 1,485 total
includes taxes & fees
9 Aug - 10 Aug
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

18. Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is AED 694
AED 2,748 total
includes taxes & fees
9 Aug - 10 Aug
Mtn-View Retreat in Huson Valley: Great for Groups

19. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 705
AED 1,596 total
includes taxes & fees
7 Sep - 8 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

20. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 691
AED 1,580 total
includes taxes & fees
7 Sep - 8 Sep
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Great Barrington Hotel Reviews