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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 ¥35,283
¥52,176 total
includes taxes & fees
Nov 15 - Nov 16

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 ¥32,141
¥47,780 total
includes taxes & fees
Nov 12 - Nov 13

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 ¥63,488
¥105,842 total
includes taxes & fees
Nov 12 - Nov 13

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 ¥89,851
¥191,137 total
includes taxes & fees
Nov 20 - Nov 21

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 ¥26,665
¥46,805 total
includes taxes & fees
Nov 12 - Nov 13

6. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
The price is ¥28,141
¥64,942 total
includes taxes & fees
Nov 18 - Nov 19

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 ¥54,139
¥94,514 total
includes taxes & fees
Nov 16 - Nov 17

8. Fantastic 2-bedroom house with AC in quaint Hillsdale.
Fantastic 2-bedroom house with AC in quaint Hillsdale.Hillsdale
The price is ¥60,314
¥97,594 total
includes taxes & fees
Nov 21 - Nov 22

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 ¥10,158
¥46,095 total
includes taxes & fees
Nov 16 - Nov 17

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 ¥72,685
¥130,256 total
includes taxes & fees
Dec 2 - Dec 3

11. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is ¥123,008
¥201,974 total
includes taxes & fees
Nov 18 - Nov 19

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 ¥13,491
¥33,083 total
includes taxes & fees
Nov 12 - Nov 13

13. 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 ¥25,427
¥56,946 total
includes taxes & fees
Nov 16 - Nov 17

14. 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 ¥23,141
¥56,698 total
includes taxes & fees
Nov 15 - Nov 16

15. 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 ¥50,425
¥95,328 total
includes taxes & fees
Nov 12 - Nov 13

16. 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 ¥11,110
¥31,236 total
includes taxes & fees
Nov 16 - Nov 17

17. 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 ¥31,744
¥51,730 total
includes taxes & fees
Nov 12 - Nov 13

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)

19. All the comforts of home
All the comforts of homeHudson
9.2 out of 10, Wonderful, (38 reviews)
The price is ¥16,856
¥21,013 total
includes taxes & fees
Nov 16 - Nov 17

20. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥42,537
¥94,394 total
includes taxes & fees
Nov 17 - Nov 18
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.






































































































































