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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
Dec 24 - Dec 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.
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 $108 per night
$108
includes taxes & fees
$97 per night
Dec 30 - Dec 31
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
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $99 per night
$99
includes taxes & fees
$89 per night
Jan 5 - Jan 6, 2025
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 Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $133 per night
$133
includes taxes & fees
$119 per night
Jan 6 - Jan 7, 2025
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 $113 per night
$113
includes taxes & fees
$101 per night
Dec 30 - Dec 31
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.
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 $111 per night
$111
includes taxes & fees
$99 per night
Jan 5 - Jan 6, 2025
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 $158 per night
$158
includes taxes & fees
$142 per night
Jan 6 - Jan 7, 2025
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 Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is $210 per night
$210
includes taxes & fees
$188 per night
Jan 1 - Jan 2, 2025
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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is $216 per night
$216
includes taxes & fees
$197 per night
Jan 1 - Jan 2, 2025
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.
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 $155 per night
$155
includes taxes & fees
$139 per night
Dec 30 - Dec 31
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
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
The price is $94 per night
$94
includes taxes & fees
$84 per night
Jan 5 - Jan 6, 2025
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.
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd, Lenox, MA
The price is $151 per night
$151
includes taxes & fees
$135 per night
Jan 9 - Jan 10, 2025
Free Cancellation
Reserve now, pay when you stay
14.8 mi from city center
Located in Lenox, Courtyard by Marriott Lenox Berkshires is a 1-minute drive from Kennedy Park and 6 minutes from The Mount.
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Windsor hotels essential information

Accommodation
898 hotels
Lowest Price
$94
Highest Price
$216
Popular hotels
Hotel Downstreet, The Yankee, Trademark Collection by Wyndham, Life House Berkshires, The Red Lion Inn, The Black Swan Lee - Lenox, Ascend Hotel Collection, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, The Williams Inn, Vacation Village in the Berkshires, The Constance, The Whitlock, & The Dewey By The Lenox Collection, Quality Inn, Courtyard by Marriott Lenox Berkshires

Most Recent Windsor Hotel Reviews

The Red Lion Inn

The Red Lion Inn

5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"Lively plae"
A verified traveler stayed at The Red Lion Inn
The Red Lion Inn