Luxury Hotels & Resorts in Windsor

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Check availability on Windsor Luxury Hotels

Tonight
2 Nov - 3 Nov
Tomorrow
3 Nov - 4 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

Best Windsor Luxury Hotels

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Good location; reasonable price; very clean and quiet - would definitely return"
Steven 2-night trip
Posted 5 days ago
Vacation Village in the Berkshires

Frequently asked questions

Are you searching for a great accommodation for your luxury getaway to Windsor?
Expedia can help you arrange a flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Westfield, MA (BAF-Barnes Municipal) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are an important consideration when you plan a trip, so we make it easy to get what you want to make your stay relaxing and comfortable. If you want a posh hotel with fine dining, a spa or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Windsor has to offer.
When can I expect good weather in Windsor?
Planning for the weather is a good way to make your trip to Windsor relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.
What's there to see and do in Windsor?
Enjoy Windsor with a stop at Mount Greylock State Reservation Visitor Center, Mount Greylock and Barrington Stage Company. If you have some spare time during your trip, you might want to check out Berkshire Museum and Colonial Theater.

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