Hotels in Windsor, Massachusetts

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Windsor overview

Windsor is a budget-friendly place unique for its theaters. You'll enjoy the ample coffee and bar options, along with outdoor areas for horseback riding and walking. This winter paradise is home to Berkshire East Ski Resort and Bousquet Ski Area. Make some memories at Wahconah Falls State Park and Bas Ridge Golf Course. A family-friendly area, Windsor also has something for everyone.

Where to stay in Windsor

Whether you're planning to stay for a night or for the week, Windsor has accommodations to fit every need. There are 91 hotels in the Windsor area and you can shop as many as 10 deals for rooms on, some with discounts of up to 25%.
  • • 32 2-star hotels with an average price of $48 per night
  • • 35 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 Windsor

Fly in to Albany, NY (ALB-Albany Intl.), 41.8 mi (67.3 km) from downtown Windsor.

What to see around Windsor

Outdoorsy fun is on hand like horseback riding and skiing, along with attractions such as:
  • • Hawley Bog Preserve
  • • Berkshire East Ski Resort
  • • Chesterfield Gorge
  • • Bousquet Ski Area
  • • Kennedy Park
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
  • • Chester Town Hall
Here are some favorite choices:
  • • Wahconah Falls State Park
  • • Bas Ridge Golf Course
  • • Crane Museum of Papermaking
  • • Susan B. Anthony Birthplace Museum
  • • Tannery Falls

When to visit Windsor

If you're still deciding when to visit, here are the seasonal norms to help you plan:

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