
Holiday Homes in Cheshire
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Our top choices for Cheshire holiday 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 €459
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 €180
includes taxes & fees
6 Nov - 7 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 €423
includes taxes & fees
5 Nov - 6 Nov

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 €195
includes taxes & fees
5 Nov - 6 Nov

5. Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
10.0 out of 10, Exceptional, (13 reviews)
The price is €178
includes taxes & fees
8 Nov - 9 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 €431
includes taxes & fees
5 Dec - 6 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 €487
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 €505
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 €971
includes taxes & fees
17 Nov - 18 Nov

10. Greylock Cabin
Greylock CabinFlorida
10.0 out of 10, Exceptional, (7 reviews)
The price is €421
includes taxes & fees
1 Dec - 2 Dec

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)
The price is €535
includes taxes & fees
5 Nov - 6 Nov

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 €380
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 €180
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 €602
includes taxes & fees
5 Dec - 6 Dec

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 €322
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 €1,122
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 €531
includes taxes & fees
6 Nov - 7 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 €504
includes taxes & fees
9 Nov - 10 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

Quality Inn Lee - Lenox South
8/10 Good
Find out more about Cheshire
Cheshire Holiday Homes information
Number of reviews | 250 |
|---|---|
Accommodation | 292 Holiday Homes |
Lowest Price | €178 |
Highest Price | €1,122 |
































































