A lake surrounded by autumn-colored trees and hills.

Hotels with Swimming Pools in Cheshire

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Check availability on Cheshire Hotels with Swimming Pools

Our top choices for Cheshire hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
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 S$218
includes taxes & fees
12 Jul - 13 Jul
The Yankee Inn
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (926 reviews)
  • cleanliness
    Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is S$134
includes taxes & fees
12 Jul - 13 Jul
Cozy Corner Motel
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (127 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is S$227
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (423 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.
The price is S$156
includes taxes & fees
13 Jul - 14 Jul
Sunset Inn
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,011 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is S$302
includes taxes & fees
22 Jul - 23 Jul
The Red Lion Inn
Outdoor pool

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,009 reviews)
  • cleanliness
    Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
The price is S$136
includes taxes & fees
12 Jul - 13 Jul
Willows Motel Williamstown
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (875 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is S$130
includes taxes & fees
19 Jul - 20 Jul
Berkshire Inn
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is S$143
includes taxes & fees
16 Jul - 17 Jul
Howard Johnson by Wyndham Lenox
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (486 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is S$98
includes taxes & fees
12 Jul - 13 Jul
Berkshire Travel Lodge
Seasonal outdoor pool

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (105 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is S$223
includes taxes & fees
12 Jul - 13 Jul
The Springs Motel
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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Choose what matters most at hotels with a pool in Cheshire

Breakfast included
4 stars

Top Cheshire Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Front desk staff was very accommodating. She was kind to let us check in as soon as rooms were cleaned. We traveled from California and were very sleepy and that made our stay more enjoyable."
MARIA THERESA 2-night trip
Posted 12 hours ago
The Yankee Inn

Frequently asked questions

What are some accommodation options with pools in Cheshire?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge: Provides free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn: Features 3 restaurants, an outdoor pool and spa services. Berkshires Untold: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Cheshire?
Surround yourself with nature at Mount Greylock State Reservation and Cheshire Reservoir. Discover sights such as St Mary's of the Assumption Church, Mount Greylock State Reservation Visitor Center and Susan B. Anthony Birthplace Museum during your stay.
When is the best time to book a hotel with a pool in Cheshire?
Taking the local weather in Cheshire into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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