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Our top choices for Great Barrington vacation homes

1. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
The price is AED 735
AED 1,112 total
includes taxes & fees
13 Dec - 14 Dec

2. A Cozy Berkshire Escape l Close to the Slopes
A Cozy Berkshire Escape l Close to the SlopesGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is AED 744
AED 1,102 total
includes taxes & fees
16 Nov - 17 Nov

3. Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 1,502
AED 2,490 total
includes taxes & fees
16 Nov - 17 Nov

4. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
10.0 out of 10, Exceptional, (10 reviews)
The price is AED 2,033
AED 4,367 total
includes taxes & fees
20 Nov - 21 Nov

5. Sweet Cozy Victorian in Housatonic. Close to everything.
Sweet Cozy Victorian in Housatonic. Close to everything.Housatonic
9.8 out of 10, Exceptional, (12 reviews)
The price is AED 646
AED 1,120 total
includes taxes & fees
16 Nov - 17 Nov

6. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
The price is AED 651
AED 1,503 total
includes taxes & fees
18 Nov - 19 Nov

7. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
The price is AED 1,253
AED 2,187 total
includes taxes & fees
16 Nov - 17 Nov

8. Fantastic 2-bedroom house with AC in quaint Hillsdale.
Fantastic 2-bedroom house with AC in quaint Hillsdale.Hillsdale
The price is AED 1,396
AED 2,258 total
includes taxes & fees
16 Nov - 17 Nov

9. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is AED 2,847
AED 4,702 total
includes taxes & fees
30 Nov - 1 Dec

10. Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Walk into town, soak up sun on enclosed porch & steps away from nature trails!Stockbridge
10.0 out of 10, Exceptional, (42 reviews)
The price is AED 1,690
AED 3,028 total
includes taxes & fees
7 Dec - 8 Dec

11. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
The price is AED 286
AED 1,128 total
includes taxes & fees
26 Nov - 27 Nov

12. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew Lebanon
7.0 out of 10, Good, (2 reviews)
The price is AED 312
AED 778 total
includes taxes & fees
16 Nov - 17 Nov

13. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew Lebanon
8.8 out of 10, Excellent, (8 reviews)
The price is AED 257
AED 711 total
includes taxes & fees
16 Nov - 17 Nov

14. Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!Lee
10.0 out of 10, Exceptional, (12 reviews)
The price is AED 1,167
AED 2,218 total
includes taxes & fees
16 Nov - 17 Nov

15. Lake View Berkshire Retreat – Private Setting Near Lenox
Lake View Berkshire Retreat – Private Setting Near LenoxLee
10.0 out of 10, Exceptional, (33 reviews)

16. 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, (10 reviews)
The price is AED 595
AED 1,391 total
includes taxes & fees
2 Dec - 3 Dec

17. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
The price is AED 654
AED 1,395 total
includes taxes & fees
14 Dec - 15 Dec

18. Luxury Barn Near Hudson With New Private Sauna
Luxury Barn Near Hudson With New Private SaunaEast Chatham
10.0 out of 10, Exceptional, (4 reviews)
The price is AED 1,374
AED 2,300 total
includes taxes & fees
18 Nov - 19 Nov

19. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.Chatham
10.0 out of 10, Exceptional, (18 reviews)
The price is AED 735
AED 1,201 total
includes taxes & fees
22 Nov - 23 Nov

20. All the comforts of home
All the comforts of homeHudson
9.2 out of 10, Wonderful, (38 reviews)
The price is AED 390
AED 486 total
includes taxes & fees
16 Nov - 17 Nov
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.
Learn more about Great Barrington
Tucked in the Berkshires, this charming town blends historic Main Street shopping with easy access to Monument Mountain's panoramic hiking trails. Visit in autumn when the maple-lined streets burst with color, or catch performances at the Mahaiwe Theatre housed in a beautifully restored 1905 building.






































































































































