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Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in 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 special. 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 temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches 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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