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Cheshire Hotels
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Our top choices for Cheshire hotels

Harbour House Inn
Harbour House Inn
9.4 out of 10, Exceptional, (51)
The price is P14,981
P15,835 total
includes taxes & fees
Aug 25 - Aug 26

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
9.0 out of 10, Wonderful, (1000)
The price is P7,217
P8,061 total
includes taxes & fees
Sep 1 - Sep 2

The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
9.0 out of 10, Wonderful, (1010)
The price is P7,128
P7,963 total
includes taxes & fees
Sep 21 - Sep 22

Berkshires Untold
Berkshires Untold
9.0 out of 10, Wonderful, (688)
The price is P9,110
P10,176 total
includes taxes & fees
Aug 26 - Aug 27

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1961)
The price is P6,172
P7,519 total
includes taxes & fees
Sep 1 - Sep 2

Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
8.8 out of 10, Excellent, (1000)
The price is P8,667
P9,681 total
includes taxes & fees
Aug 26 - Aug 27
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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Get away to romantic Cheshire! Enjoy the skiing, hiking, and lake views.

Photo by Ed Gaffny
Open Photo by Ed Gaffny
Top Cheshire Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection
10/10 Excellent
More cheap stays in Cheshire
More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is P4,502 per night from Sep 1 to Sep 2
P4,502
P5,028 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (785 reviews)
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