Cheshire Hotel Guide - Hotels with Pool in Cheshire, Massachusetts

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Check availability on Cheshire Hotels with Pool

Our top choices for Cheshire hotels with a pool

Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (897 reviews)
  • cleanliness
    Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is €80
includes taxes & fees
13 Apr - 14 Apr
Cozy Corner Motel
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (903 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is €102
includes taxes & fees
12 May - 13 May
Berkshire Mountain Lodge
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (846 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is €75
includes taxes & fees
13 Apr - 14 Apr
Howard Johnson by Wyndham Lenox
Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is €140
includes taxes & fees
19 Apr - 20 Apr
Element Lenox Berkshires
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is €106
includes taxes & fees
26 Apr - 27 Apr
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (600 reviews)
  • cleanliness
    Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
The price is €99
includes taxes & fees
13 Apr - 14 Apr
Maple Terrace Motel
Outdoor pool

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
The price is €77
includes taxes & fees
13 Apr - 14 Apr
Willows Motel Williamstown
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (88 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is €112
includes taxes & fees
16 Apr - 17 Apr
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Seasonal outdoor pool

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (95 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is €111
includes taxes & fees
16 Apr - 17 Apr
The Springs Motel
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is €166
includes taxes & fees
21 Apr - 22 Apr
The Red Lion 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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Wonderful views and staff are nice and attentive to rea"
Claire 1-night trip
Posted 8 hours ago
Vacation Village in the Berkshires

Frequently asked questions

What are some accommodation options with pools in Cheshire?
Vacation Village in the Berkshires: Features a children's pool, an indoor pool and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Offers free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Provides free self parking, an indoor pool and complimentary wireless Internet access. Berkshires Untold: Hotel located near National Shrine of the Divine Mercy. Offers 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Provides 3 restaurants, an outdoor pool and spa services.
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 Susan B. Anthony Birthplace Museum during your stay.
When is the best time to book a hotel with a pool in Cheshire?
Taking the local weather in Cheshire into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.