Book Cheap Hotels in Windsor
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Most frequently booked Windsor hotels

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 $139 per night
CA $139
CA $155 total
includes taxes & fees
24 Mar - 25 Mar
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

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 $167 per night
CA $167
CA $199 total
includes taxes & fees
30 Mar - 31 Mar
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

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 $127 per night
CA $127
CA $142 total
includes taxes & fees
3 Apr - 4 Apr
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

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 $274 per night
CA $274
CA $306 total
includes taxes & fees
25 Mar - 26 Mar
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 Schow Science Library and Denison Park are located nearby.
Pet-friendly
Parking included

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 $171 per night
CA $171
CA $211 total
includes taxes & fees
24 Mar - 25 Mar
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
Air conditioning

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 $171 per night
CA $171
CA $255 total
includes taxes & fees
14 Apr - 15 Apr
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 Tanglewood Music Center and Schantz Galleries are located nearby.
Pool
Spa

Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Free cancellation
Reserve now, pay when you stay
21.87 km from city centre
The price is CA $182 per night
CA $182
CA $203 total
includes taxes & fees
24 Mar - 25 Mar
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 MCLA Gallery 51 and North Adams Center are located nearby.
Pool
Hot tub

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 $133 per night
CA $133
CA $149 total
includes taxes & fees
30 Mar - 31 Mar
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

Hotel On North
297 North Street, Pittsfield, MA
Free cancellation
Reserve now, pay when you stay
18.1 km from city centre
The price is CA $156 per night
CA $156
CA $175 total
includes taxes & fees
30 Mar - 31 Mar
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Berkshire Athenaeum are located nearby.
Pet-friendly
Parking included
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
10/10 Exceptional! (3 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 | 938 hotels |
---|---|
Lowest Price | CA $127 |
Highest Price | CA $274 |
Popular hotels | Life House Berkshires, Vacation Village in the Berkshires, The Yankee, Trademark Collection by Wyndham, The Williams Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Red Lion Inn, Hotel Downstreet, Ascend Hotel Collection, The Black Swan Lee - Lenox, Ascend Hotel Collection, Hotel On North |
Frequently asked questions
Recent Windsor hotel reviews by fellow wanderers

The Red Lion Inn
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Loved the Inn. Great place and awesome accommodations. Staff, hotel pets, and the building are amazing."
A verified traveller from Thomaston stayed at The Red Lion Inn
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