Find 974 hotels in Windsor
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Most frequently booked hotels in Windsor

Red Roof Inn PLUS+ South Deerfield – Amherst

The Yankee, Trademark Collection by Wyndham

Vacation Village in the Berkshires

Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Williams Inn

Hotel Downstreet, Ascend Hotel Collection

Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Constance by the Lenox Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Red Lion Inn

Berkshire Mountain Lodge

Hampton Inn & Suites Berkshires-Lenox

Hotel On North
Finding Windsor Hotels
Windsor is a good place to check out, but if it's hard to find accommodation and you find yourself searching for some other options, this town nearby might have what you want.
- 3 hotels in Peru
Exploring Windsor
The city of Windsor has some interesting things to see and do. Popular attractions in and around Windsor include:
- Wahconah Falls State Park
- Mount Greylock State Reservation Visitor Center
- Swift River
- Mount Greylock
- Barrington Stage Company
- Berkshire Museum
- Colonial Theater
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 | 974 hotels |
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Lowest Price | |
Highest Price | |
Popular hotels | Red Roof Inn PLUS+ South Deerfield – Amherst, The Yankee, Trademark Collection by Wyndham, Vacation Village in the Berkshires, Best Western Plus Berkshire Hills Inn & Suites, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Williams Inn, Hotel Downstreet, Ascend Hotel Collection, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Constance by the Lenox Collection, The Black Swan Lee - Lenox, Ascend Hotel Collection, The Red Lion Inn, Berkshire Mountain Lodge, Hampton Inn & Suites Berkshires-Lenox, Hotel On North |
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