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, (1,002 reviews)
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is NT$3,253
NT$3,633 total
includes taxes & fees
May 6 - May 7
9.2 out of 10, Wonderful, (902 reviews)
- Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is NT$2,497
NT$2,943 total
includes taxes & fees
May 3 - May 4
9.0 out of 10, Wonderful, (919 reviews)
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is NT$2,725
NT$3,747 total
includes taxes & fees
May 28 - May 29
7.6 out of 10, Good, (852 reviews)
- Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is NT$2,485
NT$2,776 total
includes taxes & fees
May 5 - May 6
9.4 out of 10, Exceptional, (95 reviews)
- Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is NT$3,316
NT$3,638 total
includes taxes & fees
Apr 30 - May 1
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHGPittsfield
9.2 out of 10, Wonderful, (91 reviews)
- Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is NT$4,121
NT$4,603 total
includes taxes & fees
May 7 - May 8
8.8 out of 10, Excellent, (1,001 reviews)
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is NT$4,926
NT$6,908 total
includes taxes & fees
May 4 - May 5
9.0 out of 10, Wonderful, (1,000 reviews)
- Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
The price is NT$2,546
NT$2,844 total
includes taxes & fees
Apr 30 - May 1
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