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Cheap Windsor Hotels
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$128 nightly
The price is $143 total per night
$143 total
Jan 29 - Jan 30
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.04 mi from city center
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$126 nightly
The price is $141 total per night
$141 total
Feb 23 - Feb 24
Total with taxes and fees
Free Cancellation
13.55 mi from city center
A stay at Hotel Downstreet, an Ascend Collection Hotel places you in the heart of North Adams, within a 5-minute walk of MCLA Gallery 51 and North Adams City Hall.
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$121 nightly
The price is $136 total per night
$136 total
Feb 26 - Feb 27
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.95 mi from city center
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
Pool
Hot Tub
The Williams Inn
101 Spring Street Williamstown MA
$195 nightly
The price is $217 total per night
$217 total
Feb 8 - Feb 9
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
16.04 mi from city center
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$102 nightly
The price is $114 total per night
$114 total
Feb 6 - Feb 7
Total with taxes and fees
Free Cancellation
11.47 mi from city center
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum.
Pool
Pet friendly
Berkshires Untold
194 Pittsfield Rd Lenox MA
$98 nightly
The price is $110 total per night
$110 total
Jan 29 - Jan 30
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Pet friendly
Parking included
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$130 nightly
The price is $145 total per night
$145 total
Feb 9 - Feb 10
Total with taxes and fees
Free Cancellation
19.96 mi from city center
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Air conditioning
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$93 nightly
The price is $103 total per night
$103 total
Feb 5 - Feb 6
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.45 mi from city center
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
$98 nightly
The price is $110 total per night
$110 total
Feb 1 - Feb 2
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
22.04 mi from city center
With a stay at Red Roof Inn PLUS+ South Deerfield – Amherst in South Deerfield, you'll be within a 15-minute drive of University of Massachusetts Amherst and Yankee Candle Village.
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
$93 nightly
The price is $104 total per night
$104 total
Feb 6 - Feb 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.51 mi from city center
Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.
The Red Lion Inn
30 Main Street Stockbridge MA
$199 nightly
The price is $222 total per night
$222 total
Feb 23 - Feb 24
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.72 mi from city center
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Huttopia Berkshires
312 Kittle Rd Williamstown MA
$225 nightly
The price is $251 total per night
$251 total
Feb 1 - Feb 2
Total with taxes and fees
14.94 mi from city center
With a stay at Huttopia Berkshires in Williamstown, you'll be within a 10-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
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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Windsor hotels essential information
Accommodation | 981 hotels |
|---|---|
Lowest Price | $103 |
Highest Price | $251 |
Popular hotels | Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, Berkshire Mountain Lodge, The Williams Inn, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Red Roof Inn PLUS+ South Deerfield – Amherst, Best Western Plus Berkshire Hills Inn & Suites, The Red Lion Inn, Huttopia Berkshires |
Most Recent Windsor Hotel Reviews
Berkshire Mountain Lodge
5 out of 5
Posted 18 hours ago
CheapTickets Verified Review
"Friendly informed staff, super clean room, the hot chocolate machine !!!!!"
A verified traveler stayed at Berkshire Mountain Lodge
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