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Cheap Cheshire Hotels

Harbour House Inn

Harbour House Inn

3.5 out of 5
725 North State Road, Cheshire, MA, 01225
The price is $255 per night
1.22 mi from city center
With a stay at Harbour House Inn in Cheshire, you'll be in the mountains, within a 15-minute drive of Mass MoCA and Mount Greylock State Reservation.
19th c. Renovated Barn in the Berkshires

19th c. Renovated Barn in the Berkshires

Cheshire, MA
0.53 mi from city center
Located in Cheshire, this vacation home is in a rural location, within a 15-minute drive of Mount Greylock State Reservation and East Hoosac Quaker Meetinghouse.
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA, 01201
The price is $88 per night
Free Cancellation
Reserve now, pay when you stay
9.63 mi from city center
A stay at Berkshire Inn places you in the heart of Pittsfield, within a 15-minute walk of Colonial Theater and Berkshire Museum.
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, 01238
The price is $144 per night
17.32 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 15-minute drive of Norman Rockwell Museum 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, 01201
The price is $149 per night
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.
Yankee Inn

Yankee Inn

2.5 out of 5
461 Pittsfield Rd, Lenox, MA, 01240
The price is $123 per night
13.2 mi from city center
When you stay at Yankee Inn in Lenox, you'll be on the Strip, within a 15-minute walk of Pleasant Valley Wilderness Sanctuary and Kennedy Park.
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

2.5 out of 5
430 Main St, Williamstown, MA, 01267
The price is $237 per night
10.01 mi from city center
With a stay at Fairfield Inn & Suites by Marriott Williamstown in Williamstown, you'll be a 1-minute drive from Williams College and 8 minutes from Mass MoCA.
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA, 01237
The price is $159 per night
6.62 mi from city center
Located in Hancock, Jiminy Peak Mountain Resort is in the mountains, within a 15-minute drive of Mount Greylock State Reservation Visitor Center and Waubeeka Golf Links.
Apple Tree Inn

Apple Tree Inn

3 out of 5
10 Richmond Mountain Rd, Lenox, MA, 01240
The price is $173 per night
16.36 mi from city center
Located in Lenox, Apple Tree Inn is a 1-minute drive from Tanglewood Music Center and 9 minutes from Norman Rockwell Museum.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Hancock, MA, 01237
6.36 mi from city center
With a stay at Vacation Village in the Berkshires in Hancock, you'll be a 1-minute drive from Jiminy Peak Mountain Resort and 7 minutes from Mount Greylock State Reservation.
Econo Lodge

Econo Lodge

2.5 out of 5
16 Cheshire Road, Pittsfield, MA, 01201
The price is $84 per night
6.76 mi from city center
Located in Pittsfield, Econo Lodge is in the suburbs, a 4-minute drive from Crane Museum of Papermaking and 6 minutes from Berkshire Athenaeum.
Pilgrim Inn

Pilgrim Inn

2.5 out of 5
165 Housatonic St, Lee, MA, 01238
18.46 mi from city center
With a stay at Pilgrim Inn, you'll be centrally located in Lee, within a 15-minute drive of Norman Rockwell Museum and Housatonic River.
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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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Most Recent Cheshire Hotel Reviews

Yankee Inn

Yankee Inn

5 out of 5
Posted 1 month ago
cheaptickets Verified Review
"Everything, have stayed here before"
A verified traveler stayed at Yankee Inn
Yankee Inn