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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 591
AED 1,886 total
includes taxes & fees
5 Nov - 6 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 719 total
includes taxes & fees
5 Nov - 6 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)

4. 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
5 Nov - 6 Nov

6. 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 AED 908
AED 1,691 total
includes taxes & fees
4 Dec - 5 Dec

7. 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
22 Nov - 23 Nov

8. 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 2,087 total
includes taxes & fees
5 Nov - 6 Nov

9. 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

11. 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)

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 657
AED 1,560 total
includes taxes & fees
9 Nov - 10 Nov

13. Private room with En-suite bathroom Marigold Room
Private room with En-suite bathroom Marigold RoomShelburne Falls
The price is AED 422
AED 726 total
includes taxes & fees
8 Nov - 9 Nov

14. 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)

15. 5BR Berkshire Home Mins To The Mountain
5BR Berkshire Home Mins To The MountainCharlemont
10.0 out of 10, Exceptional, (8 reviews)

16. Ellie’s Overlook, best view in the Berkshires!
Ellie’s Overlook, best view in the Berkshires!Richmond
10.0 out of 10, Exceptional, (1 review)
The price is AED 1,157
AED 2,393 total
includes taxes & fees
8 Nov - 9 Nov

17. 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
5 Nov - 6 Nov

18. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the BerkshiresRichmond
The price is AED 3,328
AED 4,639 total
includes taxes & fees
5 Nov - 6 Nov

19. 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
5 Nov - 6 Nov

20. Spacious Central Berkshires Home for Groups
Spacious Central Berkshires Home for GroupsLee
9.6 out of 10, Exceptional, (4 reviews)
The price is AED 1,074
AED 2,086 total
includes taxes & fees
5 Nov - 6 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

Berkshires Untold
10/10 Excellent


































































