A lake surrounded by autumn-colored trees and hills.

Hotels with Swimming Pools in Cheshire

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Check availability on Cheshire Hotels with Swimming Pools

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Cheshire hotels with a pool

Indoor pool
A spacious living room with a fireplace, comfortable seating, and large windows.
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.

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.
S$129
includes taxes & fees
8 Nov - 9 Nov
Vacation Village in the Berkshires
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A hotel room with a large bed, a desk, a chair, and a view of the outdoors.
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.
S$156
includes taxes & fees
4 Nov - 5 Nov
The Springs Motel
An indoor swimming pool with blue tiles, a wooden wall, and a blue and white color scheme.
A modern bathroom with a large mirror, two sinks, a toilet, and towel racks.
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.

3. 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.
S$171
includes taxes & fees
5 Nov - 6 Nov
Hotel Downstreet, an Ascend Collection Hotel
A swimming pool with a diving board and a hot tub area.
Room
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A bathroom with a large mirror, a sink, and a towel rack.

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.
S$140
includes taxes & fees
7 Nov - 8 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

5. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
S$152
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
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.

6. 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.
S$121
includes taxes & fees
8 Nov - 9 Nov
Willows Motel Williamstown
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A room with a blue armchair, an orange armchair, a round table, a floor lamp, and a wardrobe.

7. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
S$163
includes taxes & fees
7 Nov - 8 Nov
Hampton Inn & Suites Berkshires-Lenox
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.
A hotel lobby with a reception desk, seating area with sofas and armchairs, a stone fireplace, and a television mounted on the wall.
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.
S$192
includes taxes & fees
20 Oct - 21 Oct
Jiminy Peak Mountain Resort
A swimming pool with lounge chairs and a fence.
A breakfast buffet setup with cereal, milk, juice, and pastries.
A garden with a swing set, a blue chair, and a flower bed.
A garden with a wooden pergola, potted plants, and a lawn with chairs.

9. Maple Terrace Motel

Maple Terrace Motel
Williamstown
  • Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
S$142
includes taxes & fees
1 Nov - 2 Nov
Maple Terrace Motel
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 hotel room with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall.
A covered porch with beige siding, white railings, and a row of wooden benches.

10. Cozy Corner Motel

Cozy Corner Motel
Williamstown
  • Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
S$113
includes taxes & fees
8 Nov - 9 Nov
Cozy Corner Motel
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We were surprised by the space that we got!! The lay out of the suite was so pleasant. We enjoyed the stay tremendously."
Susanna 1-night trip
Posted 8 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."
Marti 1-night trip
Posted 8 hours ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"The pool and hot tub were not heated enough. We didn't plan to use any other amenities so that was a disappointment. We enjoyed our stay. The room was good as we are our breakfast and dinner in the room. The kitchen was great and equipped with everything we needed."
Abby 2-night trip
Posted 9 hours ago
Jiminy Peak Mountain Resort
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Property was clean, staff was knowledgeable and cordial. Parking was very easy."
Julia 1-night trip
Posted 10 hours ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 3 days ago
The Red Lion Inn

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.

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