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Cheap Windsor Hotels

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 24 - Nov 25
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
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $134 per night
$134
includes taxes & fees
$120 per night
Nov 24 - Nov 25
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
Located in Lenox, Life House Berkshires is within a 15-minute walk of Kennedy Park and Pleasant Valley Wilderness Sanctuary.
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 $104 per night
$104
includes taxes & fees
$94 per night
Dec 1 - Dec 2
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 Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $181 per night
$181
includes taxes & fees
$162 per night
Dec 10 - Dec 11
Free Cancellation
Reserve now, pay when you stay
20.72 mi from city center
When you a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 5-minute walk of Housatonic River and Mission House.
Pool
Spa
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 $106 per night
$106
includes taxes & fees
$95 per night
Dec 5 - Dec 6
Free Cancellation
Reserve now, pay when you stay
16.94 mi from city center
When you stay at The Black Swan Lee - Lenox, Ascend Hotel Collection in Lee, you'll be on the waterfront, within a 5-minute drive of Berkshire Mountain Country Store and Animagic Museum of Animation.
Breakfast included
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 23 - Nov 24
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
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 $106 per night
$106
includes taxes & fees
$95 per night
Nov 30 - Dec 1
Free Cancellation
11.46 mi from city center
A stay at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel places you in the heart of Pittsfield, within a 5-minute walk of Berkshire Museum and Colonial Theater.
Pool
Pet friendly
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 $127 per night
$127
includes taxes & fees
$114 per night
Nov 26 - Nov 27
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
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 $118 per night
$118
includes taxes & fees
$106 per night
Nov 24 - Nov 25
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 walk of Lenox Library and The Bookstore.
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 1 - Dec 2
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.
Pet friendly
Parking included
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 12 - Dec 13
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
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
The price is $82 per night
$82
includes taxes & fees
$73 per night
Dec 9 - Dec 10
Free Cancellation
Reserve now, pay when you stay
17.56 mi from city center
With a stay at Quality Inn in Lee, you'll be a 1-minute walk from Housatonic River and 12 minutes by foot from Lee Library.
Breakfast included
Free WiFi
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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
884 hotels
Lowest Price
$82
Highest Price
$221
Popular hotels
Hotel Downstreet, Life House Berkshires, The Yankee, Trademark Collection by Wyndham, The Red Lion Inn, The Black Swan Lee - Lenox, Ascend Hotel Collection, Vacation Village in the Berkshires, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, The Constance, The Whitlock, & The Dewey By The Lenox Collection, The Williams Inn, Hampton Inn & Suites Berkshires-Lenox, Quality Inn

Most Recent Windsor Hotel Reviews

The Red Lion Inn

The Red Lion Inn

5 out of 5
Posted 2 days ago
CheapTickets Verified Review
"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. The dinner was delicious. Plenty of seats but gave us a table facing wall (but near window) —why not more in middle of room area with more interesting view! And same table for breakfast and dinner until we requested a different table the 2nd time. Friendly service. Twin beds very comfortable better if Full size. Happy to have 2 chairs in room. Wouldn’t stay again due to bathroom issues. "
A verified traveler stayed at The Red Lion Inn
The Red Lion Inn