Book Cheap Hotels in Windsor
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Most frequently booked Windsor hotels

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 $131 per night
CA $131
CA $161 total
Mar 9 - Mar 10
includes taxes & fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Parking included

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Free cancellation
21.82 km from city centre
The price is CA $160 per night
CA $160
CA $179 total
Mar 31 - Apr 1
includes taxes & fees
Book a stay at this business-friendly 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 MCLA Gallery 51 and North Adams Center are located nearby.
Pool
Hot tub

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
20.85 km from city centre
The price is CA $144 per night
CA $144
CA $191 total
Apr 1 - Apr 2
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub

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 $238 per night
CA $238
CA $266 total
Mar 11 - Mar 12
includes taxes & fees
Book a stay at this 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

Berkshires Untold
194 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
23.14 km from city centre
The price is CA $125 per night
CA $125
CA $140 total
Apr 5 - Apr 6
includes taxes & fees
Stay at this 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 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 $126 per night
CA $126
CA $140 total
Mar 15 - Mar 16
includes taxes & fees
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 Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free cancellation
18.47 km from city centre
The price is CA $172 per night
CA $172
CA $192 total
Mar 31 - Apr 1
includes taxes & fees
Book a stay at this 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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
Free cancellation
32.14 km from city centre
The price is CA $164 per night
CA $164
CA $209 total
Mar 10 - Mar 11
includes taxes & fees
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Air conditioning

Huttopia Berkshires
312 Kittle Rd Williamstown MA
24.05 km from city centre
The price is CA $228 per night
CA $228
CA $255 total
Mar 9 - Mar 10
includes taxes & fees
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
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
Hancock MA
10/10 Exceptional! (4 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 | 996 hotels |
|---|---|
Lowest Price | CA $140 |
Highest Price | CA $266 |
Popular hotels | Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, Berkshire Mountain Lodge, The Williams Inn, Berkshires Untold, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Huttopia Berkshires |
Frequently asked questions
Recent Windsor hotel reviews by fellow wanderers

The Yankee, Trademark Collection by Wyndham
5 out of 5
Posted 10 hours ago
Travelocity Verified Review
"
The overall property was clean and well kept the pool and Hot Tub are very nice. The breakfast was excellent.
The room we stayed in was clean. Beds were comfortable however the room was a little dated."
A verified traveller stayed at The Yankee, Trademark Collection by Wyndham
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