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Hotels with Pool & Resorts in Cheshire from AU$136

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Check availability on Cheshire Hotels with Pool

Best Cheshire Hotels with Pool

Indoor pool
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
United States
joel
The price is AU$232
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, (81)
"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 AU$171
includes taxes & fees
20 Oct - 21 Oct
The Springs Motel
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 AU$136
includes taxes & fees
20 Oct - 21 Oct
Howard Johnson by Wyndham Lenox
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, (908)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is AU$177
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (2082)
"Would def recommend anyone to stay here! Friendly, clean, all around great!! "
United States
Maria
The price is AU$175
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Indoor pool
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (716)
"Great stay, perfect "
United States
Lawrence
The price is AU$195
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge
Outdoor pool
Willows Motel Williamstown
Willows Motel Williamstown
2.0 star property
9.0 out of 10, Wonderful, (967)
"Very friendly staff and fresh fruit at breakfast!"
United States
Justin
The price is AU$153
includes taxes & fees
20 Oct - 21 Oct
Willows Motel Williamstown
Seasonal outdoor pool
Apple Tree Inn
Apple Tree Inn
3.0 star property
8.6 out of 10, Excellent, (312)
"Very clean room and comfortable bed. Friendly staff and restaurant/bar on site. "
United States
Amy
The price is AU$240
includes taxes & fees
2 Nov - 3 Nov
Apple Tree Inn
Seasonal outdoor pool
Sunset Inn
Sunset Inn
2.0 star property
7.6 out of 10, Good, (407)
"That can be reserved at any time"
United States
Felicita
The price is AU$167
includes taxes & fees
3 Nov - 4 Nov
Sunset Inn
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 AU$136
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back. "
Theresa 1-night trip
Posted 18 hours ago
Vacation Village in the Berkshires

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: Features a health club, an indoor pool and complimentary high-speed (wired) Internet access. Berkshires Untold: Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli.
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.