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Search Hotels with Pool in Cheshire

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Check availability on Cheshire Hotels with Pool

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Top Cheshire Hotels with Pool

Indoor pool
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
9.4 out of 10, Exceptional, (6)
"New hotel very nice"
United States
joel
The price is ฿4,415
฿4,932 total
includes taxes & fees
2 Nov - 3 Nov
Element Lenox Berkshires
Seasonal outdoor pool
The Springs Motel
The Springs Motel
2.0 star property
9.2 out of 10, Wonderful, (83)
"The Springs Motel was a delight! Something away from the boring, staple type of hotel. The staff was so friendly and welcoming. The coffee and breakfast is a great touch! Can't wait to go back"
United States
Tricia
The price is ฿3,351
฿3,676 total
includes taxes & fees
26 Oct - 27 Oct
The Springs Motel
Indoor pool
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (726)
"Great stay, perfect "
United States
Lawrence
The price is ฿2,510
฿3,535 total
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (919)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is ฿3,369
฿3,763 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (814)
"We enjoyed our stay. It's basic but clean and comfortable."
United States
Kit Ping
The price is ฿2,584
฿2,886 total
includes taxes & fees
26 Oct - 27 Oct
Howard Johnson by Wyndham Lenox
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2100)
"Great place!"
United States
Nicole
The price is ฿3,000
฿3,710 total
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1004)
"Very clean, nice amenities , great location!!"
United States
Erin
The price is ฿3,637
฿4,062 total
includes taxes & fees
9 Nov - 10 Nov
Hampton Inn & Suites Berkshires-Lenox
Indoor pool, seasonal outdoor pool, pool loungers
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1019)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
United States
Susan M
The price is ฿3,877
฿4,330 total
includes taxes & fees
2 Nov - 3 Nov
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
9.4 out of 10, Exceptional, (55)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is ฿4,142
฿4,627 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
Cozy Corner Motel
Cozy Corner Motel
2.0 star property
9.2 out of 10, Wonderful, (877)
"Very nice staff, nice breakfast"
United States
Kerri
The price is ฿2,443
฿2,884 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Corner 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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is a historical hotel and indeed the history is fabulous, everything appears like it did in 1773. Trouble is the rooms are also like this and the beds felt like they were 200 years old - so very uncomfortable. All part of the experience. Our room faced the street and I was surprised how much traffic noise kept me up until late at night, next time I will request a room facing inward. Not enough staff at the bar and dining during peak weekends, took forever just to get a cup of hot chocolate for the kids. But, very quaint, beautiful, that Main Street is just classic. "
Jane 2-night trip
Posted 4 days ago
The Red Lion Inn
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 3 weeks ago
Jiminy Peak Mountain Resort

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. Berkshire Mountain Lodge: Features a health club, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides free self parking, an indoor pool and complimentary wireless Internet access. Berkshires Untold: 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.