Photo by Ed Gaffny

Search Resorts in Cheshire

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Compare 1 Resorts in Cheshire with updated reviews, rates, and availability.

Holiday Inn Club Vacations Oak 'n Spruce Resort

2.0 star property
Holiday Inn Club Vacations Oak 'n Spruce 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 property types in Cheshire

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1771)
"Affordable but, Not an updated property, it works. Fire place didn’t operate in our room and the 1 bedrooms don’t have a full stove just a convection cooktop. However, the view of the slopes from this property is amazing. It’s literally 3 min drive to Jiminy Peek. "
The price is NT$3,575
NT$4,250 total
includes taxes & fees
Mar 3 - Mar 4
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is NT$6,200
NT$6,801 total
includes taxes & fees
Mar 2 - Mar 3
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.

Frequently asked questions

What is Cheshire like for a resort vacation?
You deserve a vacation, and a resort is just the place to find all the amenities and services you need for a relaxing trip to Cheshire. One of the comfortable resorts in the area might be just what you’re looking for, whether you’re hoping for a luxurious suite, shopping possibilities, or fun activities to try.
What can I do in Cheshire?
Mount Greylock State Reservation and St Mary’s of the Assumption Church are a few of the interesting sights to visit. In the area, other attractions include Mount Greylock State Reservation Visitor Center and Mount Greylock.
What's the weather like in Cheshire?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Cheshire?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) from the city center. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.