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Cheap Windsor Hotels

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $184 per night
$184
includes taxes & fees
$164 per night
Dec 2 - Dec 3
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.
Pool
Spa
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $121 per night
$121
includes taxes & fees
$108 per night
Nov 11 - Nov 12
14.37 mi from city center
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Pet friendly
Parking included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $94 per night
$94
includes taxes & fees
$84 per night
Nov 12 - Nov 13
Free Cancellation
Reserve now, pay when you stay
13.45 mi from city center
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and Company.
Pool
Hot Tub
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
The price is $115 per night
$115
includes taxes & fees
$103 per night
Nov 19 - Nov 20
Free Cancellation
Reserve now, pay when you stay
16.94 mi from city center
With a stay at The Black Swan Lee - Lenox, Ascend Hotel Collection in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.
Breakfast included
Pet friendly
Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
The price is $144 per night
$144
includes taxes & fees
$129 per night
Nov 10 - Nov 11
Free Cancellation
Reserve now, pay when you stay
13.58 mi from city center
A stay at Hotel Downstreet places you in the heart of North Adams, steps from Western Gateway Heritage State Park and 3 minutes by foot from Massachusetts Museum of Contemporary Art.
Pool
Hot Tub
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 out of 5
190 Meadow Street, South Lee, MA
The price is $166 per night
$166
includes taxes & fees
$149 per night
Nov 7 - Nov 8
Free Cancellation
19.96 mi from city center
Located in South Lee, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel is near ski lifts, within a 5-minute walk of Beartown State Forest and Housatonic River.
Pool
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
The price is $105 per night
$105
includes taxes & fees
$94 per night
Dec 6 - Dec 7
Free Cancellation
11.46 mi from city center
With a stay at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Colonial Theater.
Pool
Pet friendly
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is $195 per night
$195
includes taxes & fees
$178 per night
Nov 7 - Nov 8
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.
Pool
Kitchen
The Constance, The Whitlock, & The Dewey By The Lenox Collection

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is $98 per night
$98
includes taxes & fees
$88 per night
Nov 7 - Nov 8
16.16 mi from city center
With a stay at The Constance, The Whitlock, & The Dewey By The Lenox Collection in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and Lenox Library.
Breakfast included
Parking included
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is $221 per night
$221
includes taxes & fees
$197 per night
Dec 3 - Dec 4
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.
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
The price is $88 per night
$88
includes taxes & fees
$79 per night
Nov 7 - Nov 8
Free Cancellation
Reserve now, pay when you stay
8.46 mi from city center
Located in Pittsfield, FairBridge Inn Express is in the suburbs, a 4-minute drive from Crane Museum of Papermaking and 6 minutes from Berkshire Athenaeum.
Parking included
Free WiFi
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
The price is $132 per night
$132
includes taxes & fees
$118 per night
Dec 1 - Dec 2
Free Cancellation
Reserve now, pay when you stay
13.51 mi from city center
Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Arrowhead Museum.
Pool
Breakfast included
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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
874 hotels
Lowest Price
$88
Highest Price
$221
Popular hotels
The Red Lion Inn, Life House Berkshires, The Yankee, Trademark Collection by Wyndham, The Black Swan Lee - Lenox, Ascend Hotel Collection, Hotel Downstreet, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Vacation Village in the Berkshires, The Constance, The Whitlock, & The Dewey By The Lenox Collection, The Williams Inn, FairBridge Inn Express, Hampton Inn & Suites Berkshires-Lenox

Most Recent Windsor Hotel Reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5 out of 5
Posted 2 days ago
CheapTickets Verified Review
"The room and property was clean and the staff was accommodating and friendly. In the morning we had a very nice breakfast with a great view of the lake. There is a restaurant on the premises that served Indian cuisine. We did not have enough time to have dinner there but it did smell good. "
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection