Hotels in Cheshire
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Aug 24 - Aug 25Tomorrow
Aug 25 - Aug 26This weekend
Aug 28 - Aug 30Next weekend
Sep 4 - Sep 6Where to stay in Cheshire?
Harbour House Inn
Harbour House InnCheshire
$254
$268 total
includes taxes & fees
Aug 27 - Aug 28
The Springs Motel
The Springs MotelNew Ashford
$123
$135 total
includes taxes & fees
Sep 9 - Sep 10
FairBridge Inn Express
FairBridge Inn ExpressPittsfield
$62
$69 total
includes taxes & fees
Aug 26 - Aug 27
The Revival House
The Revival HouseAdams
$166
$185 total
includes taxes & fees
Aug 31 - Sep 1
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
$149
$166 total
includes taxes & fees
Sep 1 - Sep 2
Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
$118
$143 total
includes taxes & fees
Aug 31 - Sep 1
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art HotelAdams
$203
$226 total
includes taxes & fees
Sep 14 - Sep 15
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
$114
$127 total
includes taxes & fees
Sep 1 - Sep 2
Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
$109
$122 total
includes taxes & fees
Aug 26 - Aug 27
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
$119
$133 total
includes taxes & fees
Sep 22 - Sep 23
Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham WilliamstownWilliamstown
$110
$123 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Corner Motel
Cozy Corner MotelWilliamstown
$88
$104 total
includes taxes & fees
Sep 9 - Sep 10
Berkshire Inn
Berkshire InnPittsfield
$90
$101 total
includes taxes & fees
Aug 26 - Aug 27
Maple Terrace Motel
Maple Terrace MotelWilliamstown
$125
$140 total
includes taxes & fees
Sep 9 - Sep 10
Williamstown Motel
Williamstown MotelWilliamstown
$109
$122 total
includes taxes & fees
Sep 7 - Sep 8
The Central Downtown Inn & Suites
The Central Downtown Inn & SuitesPittsfield
$99
$111 total
includes taxes & fees
Aug 26 - Aug 27
Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
$105
$139 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
$119
$133 total
includes taxes & fees
Sep 24 - Sep 25
Go beyond your typical stay in Cheshire
Pet friendly
Cottage
Family friendly
Top landmarks in Cheshire
St Mary's of the Assumption Church
10.0/10 (1 review)
St Mary's of the Assumption Church is in the heart of Cheshire, so why not stop by during your stay.
Learn more about Cheshire
Cheshire is well-known for its attractions such as Mount Greylock State Reservation and Cheshire Reservoir.
See all hotels in Cheshire
Check out reviews of Cheshire hotels guests love
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"BIen situé avec pleins de restaurants accessibe à pied autour. Grand parking sécuritaire en face il y a la caserne de pompiers. Idéalement ce serait bien d'installer des bornes électriques de recharge pour les véhicules électriques. Déjeuner modeste. Pas de protéines. Pâtisseries et fruits bons. Très propre. Personnel courtois"
Quality Inn Lee - Lenox South
8/10 Good
"Clean room, surprisingly comfortable bed. Convenient, functional, for a short stay."
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"Oak’n’Spruce is a lovely resort in a wonderful area of the Berkshires. Very nice amenities, along with pools, tennis, mini golf, ping pong and other family activities. Best of all, it’s a short drive to the charming town of Stockbridge, a short drive to Tanglewood, and another short drive to Jacob’s pillow, a wonderful indoor and outdoor dance performance venue. We stay there often, and always makes four a cultural experience and wonderful family time."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"I liked the balcony overlooking the lake"
The Whitlock
8/10 Good
"This is a very quaint hotel in a fantastic location. It is easy to walk to everything in Lenox and even Tanglewood from the hotel. Just be aware it is an uphill walk back from Tanglewood. The room was very spacious and bed very comfortable. Would definitely stay here again. If looking for any opportunities to improve, only thing I can come up with is a small frig in the room. Great place!"
The Yankee Inn
8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
FairBridge Inn Express
10/10 Excellent
"It was very nice and everyone was extremely helpful"
Howard Johnson by Wyndham Lenox
8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."