- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Find vacation rentals that suit your style

Cabins

Apartments
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 793
AED 1,186 total
includes taxes & fees
9 Nov - 10 Nov

2. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is AED 744
AED 1,106 total
includes taxes & fees
8 Nov - 9 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 1,469
AED 2,449 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 2,079
AED 4,637 total
includes taxes & fees
20 Nov - 21 Nov

5. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great BarringtonGreat Barrington
The price is AED 3,322
AED 4,675 total
includes taxes & fees
8 Nov - 9 Nov

6. 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 716
AED 1,198 total
includes taxes & fees
23 Nov - 24 Nov

7. 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

8. 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 1,392
AED 2,425 total
includes taxes & fees
16 Nov - 17 Nov

9. 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 191
AED 985 total
includes taxes & fees
9 Nov - 10 Nov

10. Fantastic 2-bedroom house with AC in quaint Hillsdale.
Fantastic 2-bedroom house with AC in quaint Hillsdale.Hillsdale
The price is AED 1,469
AED 2,345 total
includes taxes & fees
23 Nov - 24 Nov

11. 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
23 Nov - 24 Nov

12. 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 4,650 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 290
AED 764 total
includes taxes & fees
30 Nov - 1 Dec

14. Spacious Central Berkshires Home for Groups
Spacious Central Berkshires Home for GroupsLee
9.6 out of 10, Exceptional, (4 reviews)

15. 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 536
AED 1,312 total
includes taxes & fees
8 Nov - 9 Nov

16. 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 2,206 total
includes taxes & fees
8 Nov - 9 Nov

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 588
AED 1,375 total
includes taxes & fees
8 Nov - 9 Nov

18. 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, (16 reviews)
The price is AED 735
AED 1,197 total
includes taxes & fees
8 Nov - 9 Nov

19. 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
8 Nov - 9 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.






























































































































