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Check prices for these dates

Next weekend
14 Saf. - 16 Saf.
In two weeks
21 Saf. - 23 Saf.
In one month
7 Rab. I - 9 Rab. I
In two months
4 Rab. II - 6 Rab. II

Compare Resorts in Windsor with updated reviews, rates, and availability.

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Other property types in Windsor

Vacation Village in the Berkshires
Exterior

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is SAR 563
SAR 655 total
includes taxes & fees
10 Feb - 11 Feb
Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is SAR 897
SAR 1,002 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is SAR 709
SAR 778 total
includes taxes & fees
10 Feb - 11 Feb
Jiminy Peak Mountain Resort
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.

Frequently asked questions

What is Windsor like for a resort vacation?
You deserve a getaway, and a resort is the perfect place to pamper yourself with the amenities and services you need for a relaxing stay in Windsor. One of the comfortable resorts in the area might be just what you’re looking for, whether you’re hoping for great restaurants on site, blissful spa treatments, or nightly entertainment options.
What's a favorite resort for my stay in Windsor?
Here are our top-rated resorts near Windsor: SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires! - Ski resort right by Jiminy Peak Mountain Resort. 12.9 mi (20.8 km) from Windsor. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort steps from Jiminy Peak Mountain Resort. 12.9 mi (20.7 km) from Windsor. Amenities include ski-in/ski-out access, a fitness center, and a garden. All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - Only a 5-minute walk from Jiminy Peak Mountain Resort. 12.8 mi (20.7 km) from Windsor. Access to a sauna.
What can I do in Windsor?
Wahconah Falls State Park, Savoy Mountain State Forest, and Mount Greylock State Reservation Visitor Center are a few interesting places to visit nearby. In the area, other attractions include Mohawk Trail State Forest and Mount Greylock.
What's the weather like in Windsor?
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 the best way to get to and around Windsor?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) from the city center. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.