A lake surrounded by autumn-colored trees and hills.

Find Hotels with a Pool in Cheshire, MA from CA $123

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Check availability on Cheshire Hotels with a Pool

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15

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 clean and on a beautiful property. The beds were extremely comfortable. We enjoyed the morning breakfast, and the staff was extremely kind and helpful. If you book through Expedia - I would call ahead to verify the specifics of the room you have reserved, as Expedia’s description of the room I reserved didn’t match the description on the actual Yankee Inn website. Through Expedia, I reserved a King Deluxe with fireplace, balcony and mountain view. But the actual Yankee Inn website offers EITHER a King Deluxe with a fireplace and balcony OR King Deluxe with mountain view. The management made amends to accommodate as much as possible, but the Expedia advertising was a bit misleading in my opinion."
Kimberly 2-night trip
Posted 19 hours ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Rooms were clean, nice beds and new kitchen accessories."
Linda 1-night trip
Posted 6 days ago
Jiminy Peak Mountain Resort

Frequently asked questions

What are some accommodations with pools in Cheshire?
Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. The Yankee Inn: Provides a seasonal outdoor pool, an indoor pool, and buffet. Berkshires Untold: Offers daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Features 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in Cheshire?
Surround yourself with nature at Mount Greylock State Reservation and Cheshire Reservoir. 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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