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Cheshire Holiday Rentals

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Check prices for these dates

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30 Jul - 31 Jul
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1 Aug - 3 Aug
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8 Aug - 10 Aug

Holiday 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, (1915)
"Great stay with all plenty of things to do…"
The price is S$139
includes taxes & fees
25 Aug - 26 Aug
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, (956)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is S$258
includes taxes & fees
3 Aug - 4 Aug
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, (123)
"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
The price is S$176
includes taxes & fees
24 Aug - 25 Aug
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.
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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The Berkshire Mountain Lodge is amazing! The layout of the hotel is designed to be walkable woth elevators conveniently located. The staff are friendly and helpful. The condo room is spectacular 👌. I enjoyed the convenience of a full kitchen and dining area, Great for entertaining. The room decor is relaxing and refreshing. The large flat-screen TV in the living area made watching movies enjoyable. The separate bedroom with king size bed was so comfortable. I loved the Olympic soze swimming 🏊‍♂️ pool. Thank you for an exceptional stay! "
Howard 1-night trip
Posted 23 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.

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.