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Cheap Cheshire 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 26 - Dec 27
Free Cancellation
Reserve now, pay when you stay
9.81 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
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
Jan 1 - Jan 2, 2025
Free Cancellation
Reserve now, pay when you stay
12.18 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
13.38 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 13 - Jan 14, 2025
Free Cancellation
Reserve now, pay when you stay
20.76 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.
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 31 - Jan 1, 2025
Free Cancellation
Reserve now, pay when you stay
17.32 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
9.15 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.
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
20.67 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 $192 per night
$192
includes taxes & fees
$171 per night
Jan 2 - Jan 3, 2025
10.41 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
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
6.49 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 $173 per night
$173
includes taxes & fees
$155 per night
Jan 1 - Jan 2, 2025
15.54 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.
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 12 - Jan 13, 2025
Free Cancellation
Reserve now, pay when you stay
18.52 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
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd, Lenox, MA
The price is $155 per night
$155
includes taxes & fees
$139 per night
Jan 23 - Jan 24, 2025
Free Cancellation
Reserve now, pay when you stay
13.94 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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Cheshire hotels essential information

Accommodation
919 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 Cheshire Hotel Reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"Love the view of the lake while having breakfast!"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection