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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.

Finding Windsor Hotels

Windsor is a good place to explore, but if it's hard to find accommodation and you're looking for more choices, these towns close by may have more of what you like.

  • 2 hotels in Savoy
  • 3 hotels in Peru
  • 15 hotels in Hinsdale

Exploring Windsor

The city of Windsor has some interesting things to see and do. Popular attractions in and around Windsor include:

  • Mount Greylock State Reservation Visitor Center
  • Mount Greylock
  • Barrington Stage Company
  • Berkshire Museum
  • Colonial Theater
  • Berkshire East Ski Resort
  • Mount Greylock State Reservation

When arranging your Windsor getaway, you can also use ebookers to search for a convenient flight into Pittsfield, MA (PSF-Pittsfield Municipal) Airport. You can narrow down your search by number of stops, airline or time of departure to find the one that'll meet your needs.

When is the Best Time to Explore Windsor?

If you're wondering when is the best time of year to visit Windsor, you might find this info about seasonal weather useful when you are planning your trip. The warmest months in Windsor are typically July and August, whereas the coldest months are usually January and February. The months with the most rain are July and August, whereas January and November have the least.

Here's an overview on how much rain you can expect and what the temperatures are going to be like:

  • From January to March, the average daytime temperature is 3°C and at night it is -10°C. Seasonal average rainfall is 283 mm.
  • If you visit between April and June, you can expect an average temp of 21°C during the day and 1°C at night. Average rainfall during this season is 388 mm.
  • The daytime average temp from July to September is 25°C and the night-time average is 10°C. Average precipitation for this season is 438 mm.
  • Between October and December, the average temp during the day is 13°C and -6°C at night. Seasonal average rain is 376 mm.
  • The annual rainfall average in Windsor is 1484 mm.

Windsor hotels essential information

Accommodation
983 hotels
Lowest Price
€68
Highest Price
€223
Popular hotels
Vacation Village in the Berkshires, Berkshire Mountain Lodge, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Hotel Downstreet, an Ascend Collection Hotel, The Red Lion Inn, Berkshires Untold, Red Roof Inn PLUS+ South Deerfield – Amherst, Howard Johnson by Wyndham Lenox, FairBridge Inn Express, The Williams Inn, The Yankee, Trademark Collection by Wyndham, Jiminy Peak Mountain Resort, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Holiday Inn Express & Suites Pittsfield - Berkshires by IHG