Photo by Ed Gaffny

Cheshire Holiday Rentals

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Check prices for these dates

Tonight
25 Feb - 26 Feb
Tomorrow
26 Feb - 27 Feb
This weekend
28 Feb - 2 Mar
Next weekend
7 Mar - 9 Mar

Holiday Rentals in Cheshire

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1767)
"What a hidden gem! Very reasonably priced and much more comfortable than a typical hotel. Would highly recommend staying here!"
The price is S$174
includes taxes & fees
3 Mar - 4 Mar
Vacation Village in the Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is S$214
includes taxes & fees
27 Feb - 28 Feb
The Ponds at Foxhollow
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is S$278
includes taxes & fees
27 Feb - 28 Feb
Jiminy Peak Mountain Resort
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.
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Other types of properties in Cheshire you may be interested in

Hotel Downstreet, Ascend Hotel Collection
Indoor pool, open 6:00 AM to 10 PM, pool loungers

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1002)
"Only stayed for one nigh during road trip through area. Didn't really use any amenities. Can't speak for area. Room was clean, updated sometime in past few years. Nothing stood out in terms of the room. The parking lot in long and narrow, and I had to park the equivalent of about 1 block away. A lot of the parking was taken up by utility vehicles. Not the end of the world, but it was rough walking through it during a snow storm. "
The price is S$177
includes taxes & fees
16 Mar - 17 Mar
Hotel Downstreet, Ascend Hotel Collection
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1767)
"What a hidden gem! Very reasonably priced and much more comfortable than a typical hotel. Would highly recommend staying here!"
The price is S$174
includes taxes & fees
3 Mar - 4 Mar
Vacation Village in the Berkshires
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.2 out of 10, Wonderful, (505)
"There are many small, single room,camp-like former motels in the Berkshires. Many tend towards shabbiness and neglect— not this one! I found my room warm and inviting with lots of little decorative touches that were imaginative and made me smile. The inclusion of a reading chair and writing desk is a huge plus for me. The bed was super comfortable, great pillows, nice linens. HVAC worked beautifully— I could reduce the temperature, a huge thing on a cold night when most folks would want to be...
The price is S$145
includes taxes & fees
11 Mar - 12 Mar
Life House 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.

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.