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

Our top choices for Cheshire hotels with a pool

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, (1,015 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is ₩281,516
₩314,453 total
includes taxes & fees
Jul 16 - Jul 17
The Yankee Inn
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, (2,446 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is ₩188,291
₩226,662 total
includes taxes & fees
Jul 22 - Jul 23
Vacation Village in the Berkshires
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (929 reviews)
  • cleanliness
    Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is ₩135,396
₩159,020 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Corner Motel
Indoor pool, open 6:00 AM to 10 PM, sun loungers

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,009 reviews)
  • cleanliness
    Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
The price is ₩253,364
₩283,008 total
includes taxes & fees
Jul 26 - Jul 27
Hotel Downstreet, an Ascend Collection Hotel
Outdoor pool

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
The price is ₩140,087
₩156,472 total
includes taxes & fees
Jul 22 - Jul 23
Willows Motel Williamstown
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (883 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is ₩147,461
₩164,713 total
includes taxes & fees
Jul 16 - Jul 17
Howard Johnson by Wyndham Lenox
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (491 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is ₩100,526
₩112,591 total
includes taxes & fees
Jul 19 - Jul 20
Berkshire Travel Lodge
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (880 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is ₩134,040
₩149,723 total
includes taxes & fees
Jul 20 - Jul 21
Berkshire Inn
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (620 reviews)
  • cleanliness
    Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
The price is ₩207,041
₩231,260 total
includes taxes & fees
Jul 21 - Jul 22
Maple Terrace Motel
Indoor pool

Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
3.0 star property
Williamstown
8.8 out of 10, Excellent, (418 reviews)
  • cleanliness
    Swim indoors year-round at this welcoming retreat with an indoor pool, hot tub, and extended pool hours for ultimate relaxation.
The price is ₩373,750
₩417,478 total
includes taxes & fees
Aug 12 - Aug 13
Fairfield Inn & Suites by Marriott Williamstown
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
"It's an attractive, well run hotel. I like the idea that breakfast is included. It is reasonably close to Tanglewood."
Donald 3-night trip
Posted 6 hours ago
The Yankee Inn

Frequently asked questions

What are some accommodations with pools in Cheshire?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Provides free self parking, an indoor pool, and complimentary wireless internet access. The Red Lion Inn: Features 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Offers buffet, an indoor pool, and complimentary wired internet access.
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.