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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

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

Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (397)
"Emma & staff were very friendly Emma was especially helpful as we booked 2 rooms in error for this same stay. Maid service was awesome and we appreciated the water coffee & tea as well as bagels etc. Enjoyed the Fireplace only want was a hot tub that would have made it the much more enjoyable apres ski "
The price is AED 590
AED 715 total
includes taxes & fees
12 Feb - 13 Feb
Mountaineer Inn
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (486)
"Rooms were very clean. Entire place smelled amazing. Very comfortable! "
The price is AED 355
AED 397 total
includes taxes & fees
12 Feb - 13 Feb
Life House Berkshires
D. Hotel Suites & Spa
Front of property

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2347)
"Staff"
The price is AED 475
AED 552 total
includes taxes & fees
2 Feb - 3 Feb
D. Hotel Suites & Spa
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (178)
"Nice stay for ski in ski out. Well thought out additional amenities. "
The price is AED 1,134
AED 1,357 total
includes taxes & fees
26 Feb - 27 Feb
Mount Snow Grand Summit Resort
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (407)
"Very modern good restaurant convienent"
The price is AED 727
AED 812 total
includes taxes & fees
3 Feb - 4 Feb
The Williams Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 star property
9.0 out of 10, Wonderful, (591)
"Plenty of room. Good location to local skiing. Clean."
The price is AED 474
AED 581 total
includes taxes & fees
2 Feb - 3 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Hotel Downstreet, Ascend Hotel Collection
Exterior

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1003)
"Easy to get to, nice location "
The price is AED 426
AED 476 total
includes taxes & fees
16 Feb - 17 Feb
Hotel Downstreet, Ascend Hotel Collection
Tru by Hilton Chicopee Springfield
Exterior

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1002)
"Our room was very clean. The breakfast was good with good assortment of choices. The lobby was a good place to hang out and have a cup of tea and work. My only complaint is the pool water was cloudy and had a strong smell of chloramines. They need to work out the chemical balance and do daily checks. Other wise it was a pleasant stay."
The price is AED 372
AED 422 total
includes taxes & fees
5 Feb - 6 Feb
Tru by Hilton Chicopee Springfield
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Excellent affordable option with a very pretty view of the lake. The 24 hour coffee and tea stand was also great. Staff were very polite and helpful. Room was very clean. Would definitely stay here again. "
The price is AED 360
AED 402 total
includes taxes & fees
2 Feb - 3 Feb
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Front of property

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"The property is historic, so the lodgings are dated along with some of the amenities. I only stayed one night and most likely would have stayed somewhere more modern if it was longer."
The price is AED 420
AED 633 total
includes taxes & fees
26 Feb - 27 Feb
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very Good, (729)
"We stay here often because it is close to our daughter’s school in New York. We love staying here and choose this hotel every time. "
The price is AED 389
AED 435 total
includes taxes & fees
7 Feb - 8 Feb
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Big Bears Lodge
Front of property

Big Bears Lodge

3.0 star property
8.8 out of 10, Excellent, (167)
"Great place had to leave my stuff in the ski room to dry off. For a bit after checkout. They we're very accommodating "
The price is AED 612
AED 674 total
includes taxes & fees
2 Feb - 3 Feb
Big Bears Lodge
Chalet 239
Room

Chalet 239

2.0 star property
9.4 out of 10, Exceptional, (56)
"Place is very new. House keeper should give little details to the inside refrigerator. Little filthy "
The price is AED 680
AED 749 total
includes taxes & fees
23 Feb - 24 Feb
Chalet 239
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Comfortable room. Very clean "
The price is AED 377
AED 421 total
includes taxes & fees
2 Mar - 3 Mar
The Yankee, Trademark Collection by Wyndham
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (680)
"Had a great stay - such a gem of a hotel. "
The price is AED 419
AED 468 total
includes taxes & fees
9 Feb - 10 Feb
Hotel On North
Red Roof Inn PLUS+ West Springfield
Exterior

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1003)
"Thank you so much !!"
The price is AED 311
AED 356 total
includes taxes & fees
12 Feb - 13 Feb
Red Roof Inn PLUS+ West Springfield
The Ellery
Exterior

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (587)
"The room was cosy and clean. The receptionist was welcoming and treated us with an unsolicited upgrade!"
The price is AED 511
AED 570 total
includes taxes & fees
2 Feb - 3 Feb
The Ellery
Motel 6 Chicopee, MA - Springfield
Exterior

Motel 6 Chicopee, MA - Springfield

2.0 star property
6.4 out of 10, (1000)
"It is a very nice property I will stay again"
The price is AED 278
AED 322 total
includes taxes & fees
2 Feb - 3 Feb
Motel 6 Chicopee, MA - Springfield
Homewood Suites by Hilton Holyoke-Springfield/North
Terrace/patio

Homewood Suites by Hilton Holyoke-Springfield/North

3.0 star property
9.0 out of 10, Wonderful, (948)
"Our stay was good. Hotel was clean and comfortable. It does need some updating but in general was good. The pictures of the suites do not match what you get. The shower is not handicap accessible for wheelchair bond guests."
The price is AED 465
AED 520 total
includes taxes & fees
6 Feb - 7 Feb
Homewood Suites by Hilton Holyoke-Springfield/North
Berkshire Mountain Lodge
Exterior

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (425)
"It is a 3 day family trip. Our stay was excellent. Room is big and tidy. The staff was very nice and accomodating.. the place is close to all.. restaurant, grocery, gas station etc.. "
The price is AED 400
AED 521 total
includes taxes & fees
2 Feb - 3 Feb
Berkshire Mountain Lodge
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.
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Other property types in Windsor

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is AED 551
AED 641 total
includes taxes & fees
3 Feb - 4 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 AED 849
AED 949 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, (924)
"Staff was exceptionally helpful and friendly."
The price is AED 694
AED 762 total
includes taxes & fees
2 Feb - 3 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?
Our top-rated resorts near Windsor: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort. 12.9 mi (20.7 km) from Windsor. Has ski-in/ski-out access, a fitness center, and a garden. SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires! - Ski resort. 12.9 mi (20.8 km) from Windsor. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers.
What can I do in Windsor?
Crane Museum of Papermaking, 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.