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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Chalets in Windsor

No exact matches found, but these alternatives could be just right

Recommended hotels in Windsor

Exterior
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is AED 275
AED 307 total
includes taxes & fees
19 Nov - 20 Nov
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
South Deerfield
7.2 out of 10, Good, (1004)
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
The price is AED 327
AED 366 total
includes taxes & fees
23 Nov - 24 Nov
Red Roof Inn PLUS+ South Deerfield – Amherst
Exterior
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (959)
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
United States
Stacey
The price is AED 324
AED 362 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (435)
"Nice place, easy check in"
United States
Robert
The price is AED 384
AED 422 total
includes taxes & fees
18 Nov - 19 Nov
Shaker Mill Inn
Front of property
Blooming Inn

Blooming Inn

3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (118)
"When visiting the friends that live in Shelburne Falls; I wouldn't stay anywhere else."
United States
christian
The price is AED 268
AED 479 total
includes taxes & fees
20 Nov - 21 Nov
Blooming Inn
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Great stay!"
United States
Ann
The price is AED 364
AED 406 total
includes taxes & fees
15 Dec - 16 Dec
The Yankee, Trademark Collection by Wyndham
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is AED 403
AED 450 total
includes taxes & fees
7 Dec - 8 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (10)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
The price is AED 496
AED 554 total
includes taxes & fees
23 Nov - 24 Nov
Element Lenox Berkshires
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (761)
"It's very good for stay over"
United States
Frances
The price is AED 253
AED 283 total
includes taxes & fees
1 Dec - 2 Dec
The Villager Motel
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (881)
"Clean, Great Staff, Quiet"
United States
john
The price is AED 274
AED 324 total
includes taxes & fees
18 Nov - 19 Nov
Cozy Corner Motel
Interior
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is AED 331
AED 369 total
includes taxes & fees
2 Dec - 3 Dec
Sunset Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (824)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
18 Nov - 19 Nov
Howard Johnson by Wyndham Lenox
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (584)
"Pool, fire pit, grounds and staff were great!"
United States
Kristy
The price is AED 364
AED 406 total
includes taxes & fees
18 Nov - 19 Nov
Maple Terrace Motel
Exterior
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1001)
"Clean room and good breakfast "
United States
Kelly
The price is AED 340
AED 380 total
includes taxes & fees
30 Nov - 1 Dec
Quality Inn
Exterior
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Room was far from spotless but overall good and nice breakfast. "
United States
Hannah
The price is AED 387
AED 432 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property grounds
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls
10.0 out of 10, Exceptional, (119)
"Lovely apartment, perfect for a short getaway for city slickers. Close to town. The apartment was great, came well-equipped and everything was as described. The deck was lovely to spend a slow morning having breakfast. "
United States
Megan N.
The price is AED 349
AED 574 total
includes taxes & fees
23 Nov - 24 Nov
In town, newly remodeled studio with private balcony
Exterior
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1004)
"Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again."
United States
Tammy
The price is AED 451
AED 504 total
includes taxes & fees
16 Dec - 17 Dec
Hotel Downstreet, an Ascend Collection Hotel
Exterior detail
Williamstown Motel

Williamstown Motel

2.0 star property
Williamstown
9.4 out of 10, Exceptional, (311)
"It was clean and in a convenient location "
United States
Karen
The price is AED 317
AED 354 total
includes taxes & fees
20 Nov - 21 Nov
Williamstown Motel
Exterior
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (758)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Exterior
Berkshire Inn

Berkshire Inn

2.0 star property
Pittsfield
7.8 out of 10, Good, (838)
"This property has a mid century motel look from the street but the rooms have been recently upgraded and are fully modern inside. A great value and comfortable place to stay"
United States
Phillip
The price is AED 288
AED 322 total
includes taxes & fees
24 Nov - 25 Nov
Berkshire Inn
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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Top Windsor Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "
Leslie 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge