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Most frequently booked Windsor hotels
![Hotel Downstreet](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/644e76fa_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hotel Downstreet
40 Main St, North Adams, MA
Free cancellation
Reserve now, pay when you stay
21.87 km from city centre
The price is CA $169 per night
CA $169
CA $189 total
includes taxes & fees
23 Feb - 24 Feb
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Massachusetts Museum of Contemporary Art and Studio 21 South are located nearby.
Pool
Hot tub
![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free cancellation
Reserve now, pay when you stay
20.99 km from city centre
The price is CA $150 per night
CA $150
CA $179 total
includes taxes & fees
11 Feb - 12 Feb
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Kitchen
![Life House Berkshires](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
23.14 km from city centre
The price is CA $138 per night
CA $138
CA $155 total
includes taxes & fees
23 Feb - 24 Feb
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Williams Inn
101 Spring Street, Williamstown, MA
Free cancellation
Reserve now, pay when you stay
25.83 km from city centre
The price is CA $318 per night
CA $318
CA $356 total
includes taxes & fees
17 Feb - 18 Feb
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Museum of Art and Chapin Library of Rare Books and Manuscripts are located nearby.
Pet-friendly
Parking included
![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
190 Meadow Street, South Lee, MA
Free cancellation
32.14 km from city centre
The price is CA $170 per night
CA $170
CA $210 total
includes taxes & fees
11 Feb - 12 Feb
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Restaurant
![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/96ff6d07_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
21.65 km from city centre
The price is CA $147 per night
CA $147
CA $164 total
includes taxes & fees
24 Feb - 25 Feb
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Guido's Marketplace and Bousquet Ski Area are located nearby.
Pool
Hot tub
![Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/83421694_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
One West Street, Pittsfield, MA
Free cancellation
18.46 km from city centre
The price is CA $146 per night
CA $146
CA $163 total
includes taxes & fees
22 Feb - 23 Feb
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly
![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/09e63194_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Red Lion Inn
30 Main Street, Stockbridge, MA
Free cancellation
Reserve now, pay when you stay
33.37 km from city centre
The price is CA $213 per night
CA $213
CA $302 total
includes taxes & fees
11 Feb - 12 Feb
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Schantz Galleries and Mission House are located nearby.
Pool
Spa
![The Black Swan Lee - Lenox, Ascend Hotel Collection](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/efd63cc2_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
Free cancellation
Reserve now, pay when you stay
27.28 km from city centre
The price is CA $148 per night
CA $148
CA $165 total
includes taxes & fees
12 Feb - 13 Feb
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.
Breakfast included
Pet-friendly
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.
Top hotels in Windsor for Extended Stay
![The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook](https://images.trvl-media.com/lodging/77000000/76790000/76788400/76788356/05845b38_y.jpg?impolicy=resizecrop&rw=402&ra=fit)
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
10/10 Exceptional! (2 reviews)
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.
Windsor hotels essential information
Accommodation | 918 hotels |
---|---|
Lowest Price | CA $138 |
Highest Price | CA $318 |
Popular hotels | Hotel Downstreet, Vacation Village in the Berkshires, Life House Berkshires, The Williams Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, The Red Lion Inn, The Black Swan Lee - Lenox, Ascend Hotel Collection |
Frequently asked questions
Recent Windsor hotel reviews by fellow wanderers
![The Yankee, Trademark Collection by Wyndham](http://images.trvl-media.com/lodging/1000000/60000/55000/54944/96ff6d07_y.jpg)
The Yankee, Trademark Collection by Wyndham
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Modern clean room that was very comfortable. Close to exit and parking. Great hut tub and pool, very clean with plenty of towels. Great value free breakfast included juice, cereal, eggs, sausage, waffle maker, fruit and pastries. Definitely will stay here again!"
A verified traveller stayed at The Yankee, Trademark Collection by Wyndham
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