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Search Hotels with Pool in Cheshire

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Check availability on Cheshire Hotels with Pool

Top Cheshire Hotels with Pool

Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very good, (952)
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
United States
Stacey
The price is Rp1.472.411
Rp1.644.693 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (10)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
The price is Rp2.253.690
Rp2.517.372 total
includes taxes & fees
20 Nov - 21 Nov
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, pool loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is Rp1.670.028
Rp1.865.421 total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (58)
"Room was far from spotless but overall good and nice breakfast. "
United States
Hannah
The price is Rp1.833.019
Rp2.047.482 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (753)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
Berkshire Mountain Lodge
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (819)
"Staff was very friendly and helpful."
United States
Pamela
The price is Rp1.318.826
Rp1.473.079 total
includes taxes & fees
14 Nov - 15 Nov
Howard Johnson by Wyndham Lenox
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (881)
"Clean, Great Staff, Quiet"
United States
john
The price is Rp1.247.042
Rp1.472.077 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Corner Motel
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (409)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is Rp1.502.460
Rp1.678.248 total
includes taxes & fees
2 Dec - 3 Dec
Sunset Inn
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
Seasonal outdoor pool
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (85)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is Rp1.814.671
Rp1.990.695 total
includes taxes & fees
14 Nov - 15 Nov
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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Top Cheshire Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
Amy 2-night trip
Posted 1 month ago
Jiminy Peak Mountain Resort

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Frequently asked questions

What are some accommodation options with pools in Cheshire?
Harbour House Inn: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool and free self parking. Vacation Village in the Berkshires: Provides free self parking, an indoor pool and complimentary wireless Internet access. Hotel Downstreet, an Ascend Collection Hotel: Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Offers a health club, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: 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.