
Search Holiday Homes in Cheshire
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
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 £384
includes taxes & fees
10 Nov - 11 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 £151
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 £354
includes taxes & fees
11 Nov - 12 Nov

4. Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
10.0 out of 10, Exceptional, (15 reviews)
The price is £149
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 £163
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 £408
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 £818
includes taxes & fees
10 Nov - 11 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)
The price is £343
includes taxes & fees
10 Nov - 11 Nov

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 £409
includes taxes & fees
10 Nov - 11 Nov

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 £447
includes taxes & fees
11 Nov - 12 Nov

11. Greylock Cabin
Greylock CabinFlorida
10.0 out of 10, Exceptional, (7 reviews)
The price is £340
includes taxes & fees
8 Dec - 9 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 £306
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 £217
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
The price is £143
includes taxes & fees
12 Nov - 13 Nov

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 £735
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 £270
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 £445
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)
The price is £285
includes taxes & fees
10 Nov - 11 Nov

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 £353
includes taxes & fees
10 Nov - 11 Nov

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 £465
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.
Find holiday rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Cheshire Hotel Reviews

The Red Lion Inn
10/10 Excellent

The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
Find out more about Cheshire
Cheshire Holiday Homes information
Number of reviews | 294 |
|---|---|
Accommodation | 299 Holiday Homes |
Lowest Price | £143 |
Highest Price | £818 |



























































