Photo by Ed Gaffny

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Check prices for these dates

Compare 31 Resorts in Cheshire with updated reviews, rates, and availability.

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is SAR 1,029
SAR 1,088 total
includes taxes & fees
3 Mar - 4 Mar
Harbour House Inn
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

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (84)
"This old barn was renovated into a great place to stay. Jane and Ian paid careful attention to details, light, colors, materials. Very comfortable and relaxing. The setting is gorgeous, and the sheep are fun. (FYI: It may be helpful to understand the layout and bathrooms: the new bathroom is at the far end of the smaller bedroom. This works great for a couple to have their own bathroom. The other bathroom is within the larger bedroom with the bunk bed, but in an area close to the door,...
19th c. Barn in the Berkshires

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1772)
"Absolutely outstanding! After a day of skiing at Jiminy my son & I checked into vacation village. Quick and efficient check in at the front desk by the gentleman working. Drove around to our bldg. unloaded our gear, changed into our swim trunks, grabbed a couple of cold ones and walked across the road to the hot tub! Just what the Dr. ordered! Our unit was clean & comfortable, slept great & were up and out early in the morning."
The price is SAR 409
SAR 486 total
includes taxes & fees
3 Mar - 4 Mar
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
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's the best resort for my stay in Cheshire?
Our top-rated resorts near Cheshire: SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires! - Ski resort right by Jiminy Peak Mountain Resort. 6.6 mi (10.6 km) from Cheshire. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort steps from Jiminy Peak Mountain Resort. 6.5 mi (10.5 km) from Cheshire. Amenities include ski-in/ski-out access, a fitness center, and a garden. All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - Only a 5-minute walk from Jiminy Peak Mountain Resort. 6.4 mi (10.4 km) from Cheshire. Access to a sauna.
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.