Cheshire Hotels with Swimming Pool

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Check prices for these dates

Tonight
9 Nov - 10 Nov
Tomorrow
10 Nov - 11 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

Our top choices for Cheshire hotels with a pool

Indoor pool

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,837 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is RM326
RM409 total
includes taxes & fees
10 Nov - 11 Nov
Vacation Village in the Berkshires
An indoor swimming pool with a colorful mural on the wall, a lifeguard station, and clear pool rules posted.

2. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
The price is RM484
RM540 total
includes taxes & fees
22 Nov - 23 Nov
Hotel Downstreet, an Ascend Collection Hotel
A poolside area with lounge chairs, umbrellas, and a swimming pool.

3. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (123 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is RM429
RM471 total
includes taxes & fees
10 Dec - 11 Dec
The Springs Motel
An indoor swimming pool with clear water, a diving area, and a view of the outdoors through large windows.

4. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
3.0 star property
Williamstown
8.8 out of 10, Excellent, (441 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 RM600
RM671 total
includes taxes & fees
15 Nov - 16 Nov
Fairfield Inn & Suites by Marriott Williamstown
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

5. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.4 out of 10, Very good, (1,004 reviews)
  • cleanliness
    Ski-in/ski-out mountain resort with refreshing pool, hot tubs, and tennis courts awaits.
The price is RM544
RM608 total
includes taxes & fees
10 Nov - 11 Nov
Jiminy Peak Mountain Resort
A rectangular swimming pool with a blue interior, surrounded by a white picket fence.

6. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.2 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 RM343
RM383 total
includes taxes & fees
10 Nov - 11 Nov
Willows Motel Williamstown
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

7. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (529 reviews)
  • cleanliness
    Float peacefully day or night at this 24-hour outdoor pool and hot tub sanctuary.
The price is RM654
RM821 total
includes taxes & fees
23 Nov - 24 Nov
The Porches Inn at Mass MoCA
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

8. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is RM515
RM576 total
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A swimming pool with lounge chairs and a fence.

9. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (648 reviews)
  • cleanliness
    Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
The price is RM402
RM449 total
includes taxes & fees
10 Nov - 11 Nov
Maple Terrace Motel
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,263 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is RM312
RM439 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
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

Frequently Asked Questions

What are some accommodation options 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 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.