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Find Hotels with a Pool in Cheshire, MA

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Check availability on Cheshire Hotels with a Pool

Top Cheshire Hotels with a Pool

Element Lenox Berkshires
3.0 star property
9.4 out of 10, Exceptional, (6)
"New hotel very nice"
United States
joel
$135 nightly
The price is $151
Nov 2 - Nov 3
Total with taxes and fees
Element Lenox Berkshires
The Springs Motel
2.0 star property
9.2 out of 10, Wonderful, (82)
"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
$95 nightly
The price is $105
Oct 21 - Oct 22
Total with taxes and fees
The Springs Motel
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
$79 nightly
The price is $88
Oct 21 - Oct 22
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (913)
"Enjoyable stay. Staff were very nice. "
United States
Claire
$103 nightly
The price is $115
Nov 2 - Nov 3
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2088)
"Great place!"
United States
Nicole
$112 nightly
The price is $125
Oct 30 - Oct 31
Total with taxes and fees
Vacation Village in the Berkshires
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (718)
"Great stay, perfect "
United States
Lawrence
$113 nightly
The price is $126
Nov 2 - Nov 3
Total with taxes and fees
Berkshire Mountain Lodge
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
$99 nightly
The price is $111
Oct 21 - Oct 22
Total with taxes and fees
Willows Motel Williamstown
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
$139 nightly
The price is $156
Nov 2 - Nov 3
Total with taxes and fees
Apple Tree Inn
Sunset Inn
2.0 star property
7.6 out of 10, Good, (407)
"That can be reserved at any time"
United States
Felicita
$88 nightly
The price is $99
Nov 7 - Nov 8
Total with taxes and fees
Sunset Inn
Cozy Corner Motel
2.0 star property
9.2 out of 10, Wonderful, (877)
"Very nice staff, nice breakfast"
United States
Kerri
$79 nightly
The price is $88
Nov 2 - Nov 3
Total with taxes and fees
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.

Top Cheshire Hotel Reviews

Frequently asked questions

What are some accommodations 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 wired internet access. Berkshires Untold: Provides 2 indoor pools, 2 outdoor 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 into account the local weather in Cheshire is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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