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Check availability on Cheshire Hotels with Pool

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

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, (1,017 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is Rp2.283.494
Rp2.550.664 total
includes taxes & fees
6 Jul - 7 Jul
The Yankee Inn
Meeting facility

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is Rp3.331.891
Rp4.523.817 total
includes taxes & fees
20 Jul - 21 Jul
The Red Lion Inn
Exterior

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (920 reviews)
  • cleanliness
    Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is Rp1.579.397
Rp1.856.419 total
includes taxes & fees
19 Jul - 20 Jul
Cozy Corner Motel
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (478 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is Rp1.208.543
Rp1.353.590 total
includes taxes & fees
6 Jul - 7 Jul
Berkshire Travel Lodge
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (870 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is Rp1.611.451
Rp1.800.012 total
includes taxes & fees
13 Jul - 14 Jul
Berkshire Inn
Outdoor pool

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (876 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is Rp1.772.793
Rp1.980.209 total
includes taxes & fees
5 Jul - 6 Jul
Howard Johnson by Wyndham Lenox
Outdoor pool

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
The price is Rp1.684.153
Rp1.881.130 total
includes taxes & fees
13 Jul - 14 Jul
Willows Motel Williamstown
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is Rp2.398.899
Rp3.080.619 total
includes taxes & fees
2 Aug - 3 Aug
Berkshire Mountain Lodge
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (418 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.
The price is Rp1.772.793
Rp1.980.210 total
includes taxes & fees
22 Jul - 23 Jul
Sunset Inn
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, (118 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is Rp3.069.792
Rp3.429.012 total
includes taxes & fees
6 Jul - 7 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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
"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical fare: eggs, cereal, yogurt, fresh fruit, bread/pastries, etc. As we were there for only one night, we did not take advantage of the outdoor pool or fire pit, but both appeared to be clean and well maintained."
Gail 1-night trip
Posted less than an hour ago
The Yankee Inn

Frequently asked questions

What are some accommodation options with pools in Cheshire?
Hotel Downstreet, an Ascend Collection Hotel: Features daily, an indoor pool and free self parking. The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Features 3 restaurants, an outdoor pool and spa services.
What is there to see and do in Cheshire?
Take in the natural beauty with a stop at Mount Greylock State Reservation. Discover sights such as St Mary's of the Assumption Church, Mount Greylock State Reservation Visitor Center and Mount Greylock 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.