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Top Cheshire Hotels with Free Parking
Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
8.6 out of 10, Excellent, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
Jeanine
The price is SAR 351
SAR 392 total
includes taxes & fees
10 Dec - 11 Dec
The Yankee, Trademark Collection by Wyndham
Lenox
9.2 out of 10, Wonderful, (1005)
"Great stay!"
Ann
The price is SAR 335
SAR 374 total
includes taxes & fees
15 Dec - 16 Dec
Shaker Mill Inn
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
Robert
The price is SAR 388
SAR 426 total
includes taxes & fees
16 Dec - 17 Dec
Harbour House Inn
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
Lorie
The price is SAR 791
SAR 836 total
includes taxes & fees
7 Jan - 8 January 2026
Blooming Inn
Shelburne Falls
9.2 out of 10, Wonderful, (124)
"Excellent! Really fun space with beautiful objects all around you. One of a kind, well run, seamless experience. "
Ben
The price is SAR 253
SAR 467 total
includes taxes & fees
9 Dec - 10 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
8.0 out of 10, Very Good, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank
The price is SAR 345
SAR 385 total
includes taxes & fees
12 Dec - 13 Dec
The Villager Motel
Williamstown
8.8 out of 10, Excellent, (764)
"It's very good for stay over"
Frances
The price is SAR 259
SAR 289 total
includes taxes & fees
9 Dec - 10 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
9.0 out of 10, Wonderful, (1003)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
Elisabeth
The price is SAR 380
SAR 424 total
includes taxes & fees
17 Dec - 18 Dec
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.
Top Cheshire Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
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Hotels near popular Cheshire Attractions
- Hotels near St Mary's of the Assumption Church
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Tanglewood Music Center
- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Green Mountain National Forest
- Hotels near National Shrine of the Divine Mercy
- Hotels near Williams College
- Hotels near Berkshire East Ski Resort
- Hotels near Bousquet Ski Area
- Hotels near The Clark Art Institute
Cheshire Hotels by Star Rating
Explore more hotels
- The Black Swan Lee - Lenox, an Ascend Collection Hotel
- Hampton Inn & Suites Berkshires-Lenox
- Best Western Plus Berkshire Hills Inn & Suites
- Hotel On North
- Courtyard by Marriott Lenox Berkshires
- Huttopia Berkshires
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- The Porches Inn at Mass MoCA
- Fairfield Inn & Suites by Marriott Williamstown
- Hilton Garden Inn Lenox Pittsfield
- Jiminy Peak Mountain Resort
- The Ponds at Foxhollow
- Quality Inn
- Howard Johnson by Wyndham Lenox
- The Constance by the Lenox Collection
- The Springs Motel
- The Villager Motel
- Element Lenox Berkshires
- Chambery Inn
- Maple Terrace Motel