A lake surrounded by autumn-colored trees and hills.

Search Hotels with Swimming Pool in Cheshire

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Check availability on Cheshire Hotels with Swimming Pool

Tonight
14 Sept - 15 Sept
Tomorrow
15 Sept - 16 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

Our top choices for Cheshire hotels with a pool

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with large windows, a fireplace, and a variety of seating options.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
₹9,092
₹11,204 total
includes taxes & fees
17 Sept - 18 Sept
Vacation Village in the Berkshires
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
A patio area with outdoor furniture, a fire pit, and potted plants.
A cozy living room with a stone fireplace, comfortable seating, and a television.

2. The Springs Motel

The Springs Motel
New Ashford
  • Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
₹10,940
₹12,001 total
includes taxes & fees
20 Sept - 21 Sept
The Springs Motel
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

3. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₹11,085
₹12,382 total
includes taxes & fees
22 Sept - 23 Sept
The Yankee Inn
A hot tub area with a pool, lounge chairs, and a caution sign.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

4. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
  • Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
₹10,989
₹12,275 total
includes taxes & fees
12 Oct - 13 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₹7,606
₹10,631 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A swimming pool with a wooden deck, lounge chairs, and umbrellas.
A wooden cabin with a covered deck, a fire pit, and string lights.
A wooden cabin with a porch and a small deck, surrounded by trees in a forest.
A cozy room with a wood-burning stove, two wooden chairs, a small table, and a window overlooking a snowy landscape.

6. Huttopia Berkshires

Huttopia Berkshires
Williamstown
  • Forest serenity and mountain trails define this Berkshires campground, complete with refreshing pool.
₹9,103
₹10,168 total
includes taxes & fees
22 Sept - 23 Sept
Huttopia Berkshires
An outdoor seating area with Adirondack chairs and potted plants.
A sign with the word "CLARM" on a grassy field with a road and trees in the background.
A covered porch with beige siding, white railings, and a row of wooden benches.
A hotel room with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall.

7. Cozy Corner Motel

Cozy Corner Motel
Williamstown
  • Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
₹8,428
₹9,907 total
includes taxes & fees
17 Sept - 18 Sept
Cozy Corner Motel
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.
A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.
A wooden cabin with a porch and steps leading to a door, surrounded by snow.
A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

8. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
  • Ski-in/ski-out mountain resort with refreshing pool, hot tubs, and tennis courts awaits.
₹13,264
₹14,816 total
includes taxes & fees
16 Sept - 17 Sept
Jiminy Peak Mountain Resort
A rectangular swimming pool with a blue interior, surrounded by a white picket fence.
A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.
A hay bale display with pumpkins and scarecrows.
A white two-story building with a porch, labeled as a motel.

9. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
  • Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
₹9,895
₹11,052 total
includes taxes & fees
17 Sept - 18 Sept
Willows Motel Williamstown
An indoor swimming pool with blue tiles, a wooden wall, and a blue and white color scheme.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A modern bathroom with a large mirror, two sinks, a toilet, and towel racks.
A modern interior with a large window, a wooden table, and bar stools.

10. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
  • Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
₹13,727
₹15,333 total
includes taxes & fees
21 Sept - 22 Sept
Hotel Downstreet, an Ascend Collection Hotel
View all properties

Choose what matters most at hotels with a pool in Cheshire

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Cheshire Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"We stopped at the red lion Inn on our travels back home from Maine. Our room was a block away from the main building and in an old house. It was very clean and comfortable. The location in town is nice."
Guy 1-night trip
Posted 12 hours ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Loved the pond trail! What a nice shift after a long day on the road."
Deborah 1-night trip
Posted 1 day ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Clean room, great location. Perfect base for a weekend in the Berkshires."
Alexandra 2-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel

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. Hotel Downstreet, an Ascend Collection Hotel: Offers daily, an indoor pool and free self parking. Berkshire Mountain Lodge: Provides free self parking, an indoor pool and complimentary wireless Internet access. The Yankee Inn: Features a seasonal outdoor pool, an indoor pool and buffet. Berkshires Untold: Features buffet, an indoor pool and complimentary high-speed (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 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.

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