Photo by Ed Gaffny
Search Vacation Homes in Cheshire
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 233 Vacation Homes in Cheshire with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (239)
The price is SAR 563
SAR 855 total
includes taxes & fees
1 Mar - 2 Mar

Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (209)

Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Retreat on Chickley River w/ EV Charger
9.6 out of 10, Exceptional, (26)

Amore Estate - beautiful room with many places to explore and relax in.
Amore Estate - beautiful room with many places to explore and relax in.
9.4 out of 10, Exceptional, (21)

Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISO
The price is SAR 1,208
SAR 2,524 total
includes taxes & fees
2 Mar - 3 Mar

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (67)
The price is SAR 983
SAR 2,033 total
includes taxes & fees
5 Mar - 6 Mar

Country Living just minutes from Everything!
Country Living just minutes from Everything!
10.0 out of 10, Exceptional, (27)

Hearts Desire is a furnished whole house in a small, colorful garden center.
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (90)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Cheshire

19th c. Barn in the Berkshires
19th c. Barn in the Berkshires
9.6 out of 10, Exceptional, (84)

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1772)
The price is SAR 409
SAR 486 total
includes taxes & fees
3 Mar - 4 Mar

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)
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.
Recent reviews of Cheshire hotels
Recent reviews of Cheshire hotels

Vacation Village in the Berkshires
5/5 Excellent
Dr.’s Orders
"Absolutely outstanding! After a day of skiing at Jiminy my son & I checked into vacation village. Quick and efficient check in at the front desk by the gentleman working. Drove around to our bldg. unloaded our gear, changed into our swim trunks, grabbed a couple of cold ones and walked across the road to the hot tub! Just what the Dr. ordered! Our unit was clean & comfortable, slept great & were up and out early in the morning."
A verified traveler stayed at Vacation Village in the Berkshires
Posted 12 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Vacation Homes in Other Destinations
More Accommodation Types in Cheshire
- Apartments in Cheshire
- Cottages in Cheshire
- B&B in Cheshire
- Condo Rentals in Cheshire
- Resorts in Cheshire
- Cabin Rentals in Cheshire
- Motels in Cheshire
- Farmstay in Cheshire
- Guest Houses in Cheshire
- Aparthotels in Cheshire
- Chalets in Cheshire
- Inns in Cheshire
- Condo Resorts in Cheshire
- Lodges in Cheshire
- Villas in Cheshire
- Hotels