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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Cheshire holiday rentals

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2168)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is ฿3,309
฿4,045 total
includes taxes & fees
7 Jan - 8 Jan 2026
Vacation Village in the Berkshires
Exterior
Huttopia Berkshires

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ฿5,413
฿6,046 total
includes taxes & fees
16 Dec - 17 Dec
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (136)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ฿6,015
฿6,718 total
includes taxes & fees
11 Dec - 12 Dec
Jiminy Peak Mountain Resort
House (4 Bedrooms) | Interior
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Cottage in Charlemont

3.0 star property
10.0 out of 10, Exceptional, (1)
"Loved this old home! Record player and records were fun to listen to. Pickle ball across the street was excellent! Well stocked kitchen great for cooking in. I had a tough time with water pressure and temperature but it could have been user error. Beds were comfortable except for the twin, which was a bit too firm! Would definitely rent here again "
United States
Amy
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!
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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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Beautiful rooms "
Russell 1-night trip
Posted 22 hours ago
Berkshire Mountain Lodge

Find out more about Cheshire

Search for holiday rentals in Cheshire on Expedia! 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!

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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.