A lake surrounded by autumn-colored trees and hills.

Find Hotels with a Pool in Cheshire, MA

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Check availability on Cheshire Hotels with a Pool

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Cheshire hotels with a pool

Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,480 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is ₩159,189
₩193,818 total
includes taxes & fees
Aug 23 - Aug 24
Vacation Village in the Berkshires
Seasonal outdoor pool

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (110 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is ₩239,641
₩262,886 total
includes taxes & fees
Aug 2 - Aug 3
The Springs Motel
Indoor pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,005 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is ₩162,814
₩181,863 total
includes taxes & fees
Aug 4 - Aug 5
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (934 reviews)
  • cleanliness
    Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is ₩137,876
₩161,804 total
includes taxes & fees
Jul 30 - Jul 31
Cozy Corner Motel
Outdoor pool

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,010 reviews)
  • cleanliness
    Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
The price is ₩151,079
₩168,747 total
includes taxes & fees
Aug 3 - Aug 4
Willows Motel Williamstown
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,027 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is ₩256,550
₩286,574 total
includes taxes & fees
Jul 30 - Jul 31
The Yankee Inn
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (898 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is ₩131,295
₩146,657 total
includes taxes & fees
Jul 30 - Jul 31
Berkshire Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,028 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is ₩176,211
₩229,578 total
includes taxes & fees
Aug 27 - Aug 28
Berkshire Mountain Lodge
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (1,003 reviews)
  • cleanliness
    Ski-in/ski-out mountain resort with refreshing pool, hot tubs, and tennis courts awaits.
The price is ₩261,161
₩291,717 total
includes taxes & fees
Aug 5 - Aug 6
Jiminy Peak Mountain Resort
Reception

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
The price is ₩235,513
₩263,068 total
includes taxes & fees
Aug 27 - Aug 28
Hotel Downstreet, an Ascend Collection Hotel
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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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
"First class staff and wonderful breakfast."
Larry 1-night trip
Posted 4 hours ago
The Yankee Inn

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. Hotel Downstreet, an Ascend Collection Hotel: Hotel, 6-minute walk from Massachusetts Museum of Contemporary Art. Offers daily, an indoor pool, and free self parking. The Yankee Inn: Provides a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Features 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?
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 Susan B. Anthony Birthplace Museum 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.