Hotels in Cheshire, Massachusetts

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Cheshire overview

Cheshire is a relaxing place surrounded by picturesque views of mountains. You'll find a wide variety of coffee and bar choices. Take in some of the area's local culture at Topia Arts Center and Colonial Theater. While you're here, stop by Mount Greylock State Reservation Visitor Center and Susan B. Anthony Birthplace Museum. Cheshire is a family-friendly destination while offering something for everyone.

Where to stay in Cheshire

A welcoming city for all, Cheshire has a variety of lodging options. There are 94 hotels in the Cheshire area, some with discounts of up to 25%.
  • • 34 2-star hotels with an average price of $48 per night
  • • 36 3-star hotels with an average price of $79 per night
  • • 20 4-star hotels with an average price of $90 per night
  • • 2 5-star hotels with an average price of $185 per night

How to get to Cheshire

Fly in to Albany, NY (ALB-Albany Intl.), 35.7 mi (57.5 km) from downtown Cheshire.

What to see around Cheshire

Outdoorsy fun is on hand like adventure tours and skiing, along with attractions such as:
  • • Bousquet Ski Area
  • • Clarksburg State Park
  • • Hawley Bog Preserve
  • • Kennedy Park
  • • Berkshire East Ski Resort
The area's theater and cultural sights stand out, and places to visit include:
  • • Topia Arts Center
  • • Colonial Theater
  • • 62 Center for Theater and Dance
  • • Shakespeare and Company
  • • Tanglewood Music Center
Its mountain views and hiking trails offer a glimpse of the natural beauty, and favorite spots for nature lovers include:
  • • Mount Greylock State Reservation Visitor Center
  • • Mount Greylock
  • • Wahconah Falls State Park
  • • Tannery Falls
  • • Windsor Lake Park
Here are some top sights to see:
  • • Susan B. Anthony Birthplace Museum
  • • East Hoosac Quaker Meetinghouse
  • • Crane Museum of Papermaking
  • • Waubeeka Golf Links
  • • Bas Ridge Golf Course

When to visit Cheshire

Curious about when's the best time to visit? Here are the seasonal norms to help with your planning:

Seasonal temperature averages
  • • January-March: 50°F day, 13°F night
  • • April-June: 79°F day, 29°F night
  • • July-September: 81°F day, 43°F night
  • • October-December: 65°F day, 15°F night
Seasonal rainfall averages
  • • January-March: 8.8 inches
  • • April-June: 12.9 inches
  • • July-September: 12.8 inches
  • • October-December: 12.1 inches