Photo by Ed Gaffny

Cheshire Vacation Rentals

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Vacation 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, (1746)
"Property was beautiful, great staff "
The price is P9,940
P11,493 total
includes taxes & fees
Dec 2 - Dec 3
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is P10,560
P11,584 total
includes taxes & fees
Nov 28 - Nov 29
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
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1044)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is P7,610
P8,501 total
includes taxes & fees
Dec 5 - Dec 6
Hotel Downstreet
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (442)
"Beautiful room and very comfy and convenient location."
The price is P7,062
P7,888 total
includes taxes & fees
Nov 27 - Nov 28
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1014)
"Staff was very nice, friendly and accommodating. The room was nice, clean, comfortable and spacious. "
The price is P5,248
P5,863 total
includes taxes & fees
Dec 9 - Dec 10
The Yankee, Trademark Collection by Wyndham
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 vacation rental in Cheshire?

Yes, we offer vacation rentals close to the most popular sights in Cheshire, or you can go with a more remote option if you're looking for relaxation. 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 larger area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are vacation rentals like in Cheshire?

Vacation rentals are private properties you can reserve for a couple days or more in Cheshire. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.