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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Cheshire holiday rentals

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Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,335 reviews)
"Clean rooms, and very friendly staff"
United States
Amr
The price is 2.271.208 ₫
2.825.812 ₫ total
includes taxes & fees
26 Apr - 27 Apr
Vacation Village in the Berkshires
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is 5.161.268 ₫
14.578.739 ₫ total
includes taxes & fees
23 Apr - 24 Apr
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
Two Brooks Lodge
House (4 Bedrooms) | Interior

12-acre Vacation Rental in the Berkshires!

12-acre Vacation Rental in the Berkshires!
3.0 star property
Charlemont
The price is 6.398.919 ₫
14.339.635 ₫ total
includes taxes & fees
23 Apr - 24 Apr
12-acre Vacation Rental in the 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.
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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The rooms were beautiful and the kitchen had everything needed. The staff was SUPER friendly also. My kids loved the pool and the hot tub but mainly the hot chocolate which was free. It's like they died and went to cocoa heaven藍 we will DEFINITELY be back to visit again. It was peaceful and quiet. Just what I needed. I recently lost my mom a week ago and I needed to be somewhere to get my mind right. And this resort provided that. We WILL be back.❤️"
Aszia 3-night trip
Posted 3 hours ago
Berkshire Mountain Lodge

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 5 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.