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Our top choices for The Berkshires vacation homes

1. 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 ¥25,388
¥59,338 total
includes taxes & fees
Nov 15 - Nov 16

2. 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 ¥9,667
¥45,495 total
includes taxes & fees
Nov 12 - Nov 13

3. 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 ¥23,106
¥54,311 total
includes taxes & fees
Nov 10 - Nov 11

4. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
The price is ¥34,232
¥51,159 total
includes taxes & fees
Nov 10 - Nov 11

5. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is ¥32,092
¥47,707 total
includes taxes & fees
Nov 10 - Nov 11

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 ¥26,625
¥46,735 total
includes taxes & fees
Nov 10 - Nov 11

7. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
The price is ¥28,099
¥64,844 total
includes taxes & fees
Nov 18 - Nov 19

8. Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.8 out of 10, Excellent, (12 reviews)
The price is ¥25,515
¥81,725 total
includes taxes & fees
Nov 10 - Nov 11

9. 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 ¥54,058
¥97,382 total
includes taxes & fees
Nov 10 - Nov 11

10. 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 ¥50,349
¥95,715 total
includes taxes & fees
Nov 10 - Nov 11

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 ¥72,901
¥130,643 total
includes taxes & fees
Dec 1 - Dec 2

12. 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 ¥63,392
¥105,682 total
includes taxes & fees
Nov 16 - Nov 17

13. A roomy remodeled retreat close to MassMoCA
A roomy remodeled retreat close to MassMoCANorth Adams
10.0 out of 10, Exceptional, (61 reviews)
The price is ¥39,178
¥74,386 total
includes taxes & fees
Nov 10 - Nov 11

14. Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Walk to Williams * Steam Sauna * Ritz-Carlton BedWilliamstown
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥42,790
¥86,091 total
includes taxes & fees
Nov 24 - Nov 25

15. 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 ¥89,716
¥200,053 total
includes taxes & fees
Nov 20 - Nov 21

16. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!Pittsfield
8.6 out of 10, Excellent, (11 reviews)
The price is ¥42,647
¥74,544 total
includes taxes & fees
Nov 10 - Nov 11

17. Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy PeakHancock
10.0 out of 10, Exceptional, (22 reviews)
The price is ¥99,676
¥172,886 total
includes taxes & fees
Nov 10 - Nov 11

18. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is ¥122,822
¥200,626 total
includes taxes & fees
Nov 16 - Nov 17

19. Greylock Cabin
Greylock CabinFlorida
10.0 out of 10, Exceptional, (7 reviews)
The price is ¥48,389
¥71,522 total
includes taxes & fees
Dec 8 - Dec 9

20. 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 ¥153,940
¥213,525 total
includes taxes & fees
Nov 10 - Nov 11
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 The Berkshires
Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.

Photo by Photo courtesy of Berkshire Visitors Bureau
Open Photo by Photo courtesy of Berkshire Visitors Bureau

































































































































