Best Resorts in Cheshire

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Resorts in Cheshire

Dining
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Hancock
10.0 out of 10, Exceptional, (6)
"Great location, clean and perfect for a family! "
United States
Allison A.
$629 nightly
The price is $703
Dec 31 - Jan 1, 2026
Total with taxes and fees
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
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
"I am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the many nature trails here. And the bed was so perfectly firm and cozy that I drifted effortlessly to sleep. The grounds, the amenities and the coordinated activities to bring you together in community made me feel included. Definitely a place I will continue to return to for many years."
salena 9-night trip
Posted 21 hours ago
Berkshire Mountain Lodge

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
6
Accommodation
34 Resorts
Lowest Price
$703
Highest Price
$703

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?
Here's our top-rated resort near Cheshire: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 20.6 mi (33.2 km) from Cheshire. Enjoy the sauna, fitness center, and terrace.
What can I do in Cheshire?
Mount Greylock State Reservation, St Mary's of the Assumption Church, and Mount Greylock State Reservation Visitor Center are a few interesting places to visit nearby. In the area, other attractions include Mount Greylock and Wahconah Falls State Park.
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.

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