Holiday Rentals in Cheshire County
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Our top choices for Cheshire County holiday rentals

Cabin in Fitzwilliam
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna10.0 out of 10, Exceptional, (13)
The price is €182
includes taxes & fees
17 Dec - 18 Dec
The price is €293
includes taxes & fees
17 Dec - 18 Dec

10.0 out of 10, Exceptional, (8)
The price is €212
includes taxes & fees
17 Dec - 18 Dec

Holiday Home in Keene
Downtown Hot Tub Escape9.6 out of 10, Exceptional, (21)
The price is €242
includes taxes & fees
17 Dec - 18 Dec

10.0 out of 10, Exceptional, (22)
The price is €321
includes taxes & fees
17 Dec - 18 Dec

Holiday Home in Walpole
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 910.0 out of 10, Exceptional, (50)
The price is €486
includes taxes & fees
17 Dec - 18 Dec

Holiday Home in Keene
Charming Home Walk to Downtown!10.0 out of 10, Exceptional, (2)
The price is €544
includes taxes & fees
15 Jan - 16 Jan 2026

Holiday Home in Stoddard
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston10.0 out of 10, Exceptional, (1)
The price is €403
includes taxes & fees
17 Dec - 18 Dec
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.
Top Cheshire County Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel
10/10 Excellent
Find out more about Cheshire County
Holiday Homes in Cheshire County
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