
Find Hotels with a Pool in Cheshire, MA
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Our top choices for Cheshire hotels with a pool

9.2 out of 10, Wonderful, (1,013 reviews)
cleanliness Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is NT$3,315
NT$3,703 total
includes taxes & fees
Jun 15 - Jun 16

7.6 out of 10, Good, (867 reviews)
cleanliness Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is NT$2,499
NT$2,791 total
includes taxes & fees
Jun 15 - Jun 16

9.2 out of 10, Wonderful, (915 reviews)
cleanliness Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is NT$2,676
NT$3,149 total
includes taxes & fees
Jun 17 - Jun 18

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
9.4 out of 10, Exceptional, (107 reviews)
cleanliness Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is NT$4,428
NT$4,947 total
includes taxes & fees
Jun 22 - Jun 23

9.6 out of 10, Exceptional, (611 reviews)
cleanliness Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
The price is NT$3,638
NT$4,063 total
includes taxes & fees
Jun 16 - Jun 17

9.0 out of 10, Wonderful, (979 reviews)
cleanliness Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is NT$3,848
NT$5,004 total
includes taxes & fees
Jun 25 - Jun 26

9.4 out of 10, Exceptional, (102 reviews)
cleanliness Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is NT$3,879
NT$4,255 total
includes taxes & fees
Jun 15 - Jun 16

8.8 out of 10, Excellent, (1,008 reviews)
cleanliness Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is NT$4,859
NT$6,840 total
includes taxes & fees
Jun 22 - Jun 23
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

The Red Lion Inn
10/10 Excellent
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- Bissell Covered Bridge
- Mount Greylock State Reservation Visitor Center
- Bousquet Ski Area
- Lenox Mountain
- Visit Lenox
- Pleasant Valley Wilderness Sanctuary
- Massachusetts Museum of Contemporary Art
- Williamstown Theatre Festival
- Visit Dalton
- Charlemont Federated Church
- Visit North Adams
- Visit Lanesborough
- Visit Charlemont
- Kushi Institute
- Visit Williamstown
- Visit Hancock
- Canoe Meadows Wildlife Sanctuary
- Crane Museum of Papermaking
- 62 Center for Theater and Dance
- Frelinghuysen Morris House and Studio
- Hawley Bog Preserve
- Williamstown Historical Museum
- The Clark Art Institute
- Williams College Museum of Art
- North Adams Public Library







































