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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, (1672)
"Very nice spot quiet "
The price is P 9,710
per night
May 4 - May 5
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Private kitchen
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (856)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is P 8,573
per night
May 7 - May 8
Jiminy Peak Mountain Resort
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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.

Other types of properties in Cheshire you may be interested in

Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.2 out of 10, Wonderful, (232)
"Very accommodating and friendly staff. Coffee in the morning was excellent. "
The price is P 5,696
per night
May 6 - May 7
Life House Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1004)
"Great visit to The Black Swan Inn. Perfectly located central to activities in the Berkshires. Fantastic customer service and very clean."
The price is P 5,820
per night
May 9 - May 10
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1001)
"My overall experience at the Yankee was very good, my only complaint is the shower. The water took forever to warm up and when it eventually did it was moderately warm, never got hot, and the water pressure was poor. Otherwise my stay there was all I needed it to be"
The price is P 6,798
per night
May 9 - May 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.

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
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  • 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!

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.

Recent reviews of Cheshire properties
Expedia verified reviews

The Red Lion Inn

The Red Lion Inn

5/5 Excellent
"Quaint, quiet and peaceful."
A verified traveler stayed at The Red Lion Inn
Posted 1 day ago
The Red Lion Inn