Photo by Ed Gaffny

Cheshire Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 11 - Nov 12
Tomorrow
Nov 12 - Nov 13
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Cheshire

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2131)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is ₩134,041
₩165,754 total
includes taxes & fees
Nov 12 - Nov 13
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (984)
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
United States
Philip
The price is ₩216,989
₩242,377 total
includes taxes & fees
Nov 25 - Nov 26
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ₩322,945
₩360,729 total
includes taxes & fees
Dec 12 - Dec 13
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Good "
Joy 1-night trip
Posted 13 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Cheshire

Search for Vacation rentals in Cheshire on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Cheshire using one of the methods below:

  • View our selection of featured Vacation rentals in Cheshire
  • Use the map to find apartments and other Vacation homes in the Cheshire neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Cheshire while they last

Look no further and take a look at our great range of rental properties in Cheshire!

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we offer vacation rentals close to the most popular sights in Cheshire, or you can go with a more remote option if you're looking for relaxation. Cheshire is known for its ski areas and restaurants. Make sure you have time to check out the lake views and shopping during your trip.

How many vacation rentals are there in Cheshire?

Expedia has 4 vacation rentals for your stay in Cheshire.

What can I see and do in Cheshire?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Mount Greylock State Reservation. In the larger area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are vacation rentals like in Cheshire?

Vacation rentals are private properties you can reserve for a couple days or more in Cheshire. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.