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Cheshire Hotels
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Top 10 trending Cheshire hotels

Harbour House Inn
Harbour House Inn
9.4 out of 10, Exceptional, (50)
The price is P14,801
P15,644 total
includes taxes & fees
Jul 8 - Jul 9

Berkshire Valley Inn
Berkshire Valley Inn
9.2 out of 10, Wonderful, (549)
The price is P8,873
P9,911 total
includes taxes & fees
Jul 31 - Aug 1

Maple Terrace Motel
Maple Terrace Motel
9.6 out of 10, Exceptional, (565)
The price is P7,843
P8,761 total
includes taxes & fees
Jul 9 - Jul 10

Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott Williamstown
8.8 out of 10, Excellent, (354)
The price is P12,639
P14,118 total
includes taxes & fees
Jul 8 - Jul 9

Blooming Inn
Blooming Inn
9.2 out of 10, Wonderful, (101)
The price is P4,977
P7,760 total
includes taxes & fees
Jul 9 - Jul 10

The Constance by the Lenox Collection
The Constance by the Lenox Collection
8.6 out of 10, Excellent, (485)
The price is P9,855
P11,008 total
includes taxes & fees
Jul 15 - Jul 16
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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Family-friendly hotels in Cheshire you'll enjoy

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
6.2 out of 10, (605)
The price is P3,597
P4,018 total
includes taxes & fees
Aug 3 - Aug 4
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.
Learn more about Cheshire
Get away to romantic Cheshire! Enjoy the skiing, hiking, and wildlife.

Photo by Ed Gaffny
Open Photo by Ed Gaffny
More cheap stays in Cheshire
More cheap stays in Cheshire

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
The price is P6,667 per night from Jul 13 to Jul 14
P6,667
P7,447 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
Near an Attraction
Near an Attraction
Recent Reviews in Cheshire
Recent Reviews in Cheshire

Jiminy Peak Mountain Resort
5/5 Excellent
"Did not use any amenities to speak of. But it was the perfect place to spend the night. No issues. Lovely bedrooms and living area. If we had more time I would have read my book on the peaceful deck. Well stocked with toiletries and extra blankets/pillows. "
A verified traveler stayed at Jiminy Peak Mountain Resort
Posted 1 day ago
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