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
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Vacation Rentals in Cheshire

Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2098)
"Great place!"
United States
Nicole
The price is RM388
RM479 total
includes taxes & fees
3 Nov - 4 Nov
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (983)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is RM630
RM703 total
includes taxes & fees
26 Oct - 27 Oct
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (132)
"All as promised!"
United States
Arthur
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Our room was clean as a pin and we loved the option of daily maid service. Love that there’s a closet with adequate hangers, extra blanket, clock, and the shampoo, body wash dispensers in the shower. Towels were big and fluffy. LOVE the heat lamp in the bathroom!"
Douglas 2-night trip
Posted 18 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Cheshire

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

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

Yes, there are holiday rentals close to the most popular sights in Cheshire, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals are there in Cheshire?

Expedia has 4 holiday 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 wider area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are holiday rentals like in Cheshire?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheshire. Holiday rentals feature extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family gatherings.