A lake surrounded by autumn-colored trees and hills.

Hotels with Swimming Pool in Cheshire, Massachusetts

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Check availability on Cheshire Hotels with Swimming Pool

Tonight
Aug 23 - Aug 24
Tomorrow
Aug 24 - Aug 25
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

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 a fireplace, comfortable seating, and large windows.

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.
P5,361
P6,665 total
includes taxes & fees
Aug 31 - Sep 1
Vacation Village in the Berkshires
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A cozy living room with a stone fireplace, comfortable seating, and a television.
A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

2. The Springs Motel

The Springs Motel
New Ashford
  • Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
P7,359
P8,073 total
includes taxes & fees
Aug 24 - Aug 25
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.
P9,751
P10,891 total
includes taxes & fees
Sep 14 - Sep 15
The Yankee Inn
An indoor swimming pool with clear water, surrounded by white lounge chairs and a tiled deck.
A modern bar area with a central island, multiple bar stools, and a seating area with tables and chairs.
A Holiday Inn & Suites hotel with a modern design, featuring a prominent sign and a well-lit entrance.
A banquet hall with round tables set for a formal event, featuring white tablecloths, silverware, and floral centerpieces.

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.
P7,344
P8,203 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 reception area with a large landscape painting, a dark reception desk, and a potted plant.
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

5. 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.
P9,180
P10,254 total
includes taxes & fees
Sep 1 - Sep 2
Hotel Downstreet, an Ascend Collection Hotel
An outdoor seating area with Adirondack chairs and potted plants.
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.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

6. Cozy Corner Motel

Cozy Corner Motel
Williamstown
  • Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
P5,443
P6,398 total
includes taxes & fees
Sep 9 - Sep 10
Cozy Corner Motel
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 patio area with wooden chairs and tables, surrounded by dense greenery and trees.
A hay bale display with pumpkins and scarecrows.

7. 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.
P6,390
P7,138 total
includes taxes & fees
Aug 24 - Aug 25
Willows Motel Williamstown
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
P5,838
P7,900 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
A swimming pool with a wooden deck, lounge chairs, and umbrellas.
A tent with a bed, a small bathroom with a sink and toilet, and a mirror.
A cozy room with a wood-burning stove, two wooden chairs, a small table, and a window overlooking a snowy landscape.
A wooden cabin with a porch and a small deck, surrounded by trees in a forest.

9. Huttopia Berkshires

Huttopia Berkshires
Williamstown
  • Forest serenity and mountain trails define this Berkshires campground, complete with refreshing pool.
P5,999
P6,700 total
includes taxes & fees
Sep 8 - Sep 9
Huttopia Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.
A motel with a parking lot, a swimming pool, and outdoor seating.
A bathroom with a bathtub, toilet, and shower.

10. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
P5,554
P6,203 total
includes taxes & fees
Aug 24 - Aug 25
Berkshire Inn
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I liked the balcony overlooking the lake"
Rinat 3-night trip
Posted 4 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 1 day ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Price - quality =awesome"
Anastasia 3-night trip
Posted 1 day ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
Evan M 1-night trip
Posted 1 day ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"I had 2 rooms. 1 room (414) did not have a phone, the microwave didn't have power. The other room was fine. We didn't like that there was only 1 elevator working as we had to wait quite a while sometimes to go up or down. We understand that the hotel is undergoing renovations. Overall, we enjoyed our stay."
Frank 2-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

What are some accommodations 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. The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Provides free self parking, an indoor pool, and complimentary wireless internet access. FairBridge Inn Express: Features buffet, an indoor pool, and complimentary wired internet access. Berkshires Untold: Offers 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 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.

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