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Our top choices for Cheshire vacation homes

1. 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 AED 1,183
AED 2,543 total
includes taxes & fees
23 Nov - 24 Nov

2. 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 723 total
includes taxes & fees
10 Nov - 11 Nov

3. 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 AED 988
AED 1,732 total
includes taxes & fees
19 Nov - 20 Nov

4. Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
10.0 out of 10, Exceptional, (15 reviews)
The price is AED 426
AED 716 total
includes taxes & fees
15 Nov - 16 Nov

5. 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 782 total
includes taxes & fees
10 Nov - 11 Nov

6. 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 AED 992
AED 1,995 total
includes taxes & fees
24 Nov - 25 Nov

7. Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy PeakHancock
10.0 out of 10, Exceptional, (22 reviews)
The price is AED 2,310
AED 4,007 total
includes taxes & fees
17 Nov - 18 Nov

8. A roomy remodeled retreat close to MassMoCA
A roomy remodeled retreat close to MassMoCANorth Adams
10.0 out of 10, Exceptional, (61 reviews)

9. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ DeckStephentown
9.2 out of 10, Wonderful, (10 reviews)
The price is AED 746
AED 2,039 total
includes taxes & fees
9 Dec - 10 Dec

10. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to WilliamstownPownal
10.0 out of 10, Exceptional, (41 reviews)
The price is AED 1,157
AED 2,160 total
includes taxes & fees
11 Nov - 12 Nov

11. Greylock Cabin
Greylock CabinFlorida
10.0 out of 10, Exceptional, (7 reviews)
The price is AED 1,121
AED 1,658 total
includes taxes & fees
10 Dec - 11 Dec

12. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 602
AED 1,493 total
includes taxes & fees
10 Nov - 11 Nov

13. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT RetreatBennington
8.6 out of 10, Excellent, (36 reviews)
The price is AED 422
AED 1,055 total
includes taxes & fees
11 Nov - 12 Nov

14. Private room with En-suite bathroom Marigold Room
Private room with En-suite bathroom Marigold RoomShelburne Falls

15. 5BR Berkshire Home Mins To The Mountain
5BR Berkshire Home Mins To The MountainCharlemont
10.0 out of 10, Exceptional, (8 reviews)
The price is AED 2,070
AED 3,617 total
includes taxes & fees
21 Nov - 22 Nov

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 536
AED 1,312 total
includes taxes & fees
10 Nov - 11 Nov

17. 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
10 Nov - 11 Nov

18. Shelburne Falls on Main
Shelburne Falls on MainShelburne Falls
10.0 out of 10, Exceptional, (1 review)

19. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11Whitingham
10.0 out of 10, Exceptional, (16 reviews)
The price is AED 1,315
AED 2,489 total
includes taxes & fees
10 Dec - 11 Dec

20. 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 2,257 total
includes taxes & fees
10 Nov - 11 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.
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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge
10/10 Excellent





























































