Find Hotels with a Pool in Cheshire, MA

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Check availability on Cheshire Hotels with a Pool

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

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, (1,000 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is ₩208,497
₩232,887 total
includes taxes & fees
Jun 16 - Jun 17
The Yankee Inn
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (856 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is ₩118,498
₩132,361 total
includes taxes & fees
May 29 - May 30
Howard Johnson by Wyndham Lenox
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (958 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is ₩174,147
₩228,033 total
includes taxes & fees
May 31 - Jun 1
Berkshire Mountain Lodge
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (910 reviews)
  • cleanliness
    Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is ₩126,898
₩149,308 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Corner Motel
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, (607 reviews)
  • cleanliness
    Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
The price is ₩172,498
₩192,688 total
includes taxes & fees
Jun 8 - Jun 9
Maple Terrace Motel
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (99 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is ₩202,497
₩226,189 total
includes taxes & fees
May 31 - Jun 1
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is ₩255,146
₩352,019 total
includes taxes & fees
Jun 22 - Jun 23
The Red Lion Inn
Seasonal outdoor pool

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (97 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is ₩213,747
₩234,481 total
includes taxes & fees
Jun 1 - Jun 2
The Springs Motel
Outdoor pool

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
The price is ₩125,398
₩140,083 total
includes taxes & fees
Jun 8 - Jun 9
Willows Motel Williamstown
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (413 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
The price is ₩164,998
₩184,303 total
includes taxes & fees
May 31 - Jun 1
Sunset Inn
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"This fitter needs just fine"
Dylan 1-night trip
Posted 3 hours ago
Hampton Inn & Suites Berkshires-Lenox

Frequently asked questions

What are some accommodations with pools in Cheshire?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Provides a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires: Features daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Features a seasonal outdoor pool, an indoor pool, and buffet.
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 Adams Theater 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.