Photo by Ed Gaffny

Cheshire Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
14 Jul - 15 Jul
Tomorrow
15 Jul - 16 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Vacation Rentals in Cheshire

Vacation Village in the Berkshires
Relax in a stylish living area with a large carpet, comfortable sofas, and a wooden coffee table.

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1874)
"Very nice places "
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Set amidst lush greenery, this hotel complex offers a serene escape with pathways connecting its various buildings.

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (947)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is RM685
RM765 total
includes taxes & fees
27 Jul - 28 Jul
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Steps lead down to the tranquil lake's edge, surrounded by trees and a rustic stone wall.

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
Huttopia Berkshires
Situated in a lush forest, this cabin offers a serene retreat with a picnic table for outdoor dining or relaxation.

Huttopia Berkshires

1.0 star property
Huttopia Berkshires
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
Sign in
Sign up, it's free

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.

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.