If you're looking for a place to get away, look no further than Cheshire. Whether you're planning to stay for a night or for the week, the area around Cheshire has accommodation options to fit every need. Search for hotels in Cheshire with Hotels.com by checking our online map. Our map displays the areas and neighbourhoods around all Cheshire hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Cheshire hotel deals are here with our lowest price guarantee.
Photo by Ed Gaffny
Hotels in Cheshire
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Harbour House Inn
Harbour House Inn
9.4 out of 10, Exceptional, (50)
The Revival House
The Revival House
9.6 out of 10, Exceptional, (4)
The Springs Motel
The Springs Motel
9.0 out of 10, Wonderful, (51)
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art Hotel
8.8 out of 10, Excellent, (131)
Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1889)
FairBridge Inn Express
FairBridge Inn Express
5.4 out of 10, (744)
Berkshire Valley Inn
Berkshire Valley Inn
9.2 out of 10, Wonderful, (552)
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very good, (948)
Hotel On North
Hotel On North
9.6 out of 10, Exceptional, (744)
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8.0 out of 10, Very good, (824)
Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham Williamstown
6.4 out of 10, (854)
Berkshire Inn
Berkshire Inn
7.8 out of 10, Good, (783)
1896 House Country Inn & Motels
1896 House Country Inn & Motels
6.6 out of 10, (427)
Williamstown Motel
Williamstown Motel
9.4 out of 10, Exceptional, (277)
Willows Motel Williamstown
Willows Motel Williamstown
9.0 out of 10, Wonderful, (928)
Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
8.8 out of 10, Excellent, (1002)
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
8.8 out of 10, Excellent, (298)
The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCA
9.4 out of 10, Exceptional, (395)
Maple Terrace Motel
Maple Terrace Motel
9.6 out of 10, Exceptional, (566)
The Williams Inn
The Williams Inn
9.6 out of 10, Exceptional, (470)
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.
Go beyond your typical stay in Cheshire
Pet friendly
Top landmarks in Cheshire
St Mary's of the Assumption Church
If you're interested in local religious buildings, central Cheshire is home to St Mary's of the Assumption Church.
Learn more about Cheshire
Cheshire is well known for its attractions such as Mount Greylock State Reservation and St Mary's of the Assumption Church.
Photo by Ed Gaffny
Open Photo by Ed Gaffny
Check out reviews of Cheshire hotels guests love
Berkshires Untold
10/10 Excellent
Frequently asked questions
Find out more about Cheshire
Find out more about Cheshire
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- Landmarks
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- Hotels near St Mary's of the Assumption Church
- Hotels near Tanglewood Music Center
- Hotels near Jiminy Peak Mountain Resort
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- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Mount Greylock
- Hotels near The Clark Art Institute
- Hotels near Berkshire East Ski Resort
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- Hotels near Bousquet Ski Area
- Hotels near Hancock Shaker Village
- Hotels near Mount Greylock State Reservation Visitor Center
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
- Hotels near Williamstown Theatre Festival
- Hotels near Berkshire Botanical Garden
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- Berkshire Inn
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