A lake surrounded by autumn-colored trees and hills.

Cheshire Hotel Guide - Hotels with Pool in Cheshire, Massachusetts

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Check availability on Cheshire Hotels with Pool

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 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.
An outdoor patio area with tables and chairs, green umbrellas, and a building with 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.
€90
includes taxes & fees
1 Nov - 2 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 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".

2. The Springs Motel

The Springs Motel
New Ashford
  • Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
€109
includes taxes & fees
4 Nov - 5 Nov
The Springs 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 hay bale display with pumpkins and scarecrows.
A white two-story building with a porch, labeled as a motel.

3. 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.
€84
includes taxes & fees
1 Nov - 2 Nov
Willows Motel Williamstown
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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

4. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
€108
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn
A swimming pool with a diving board and a hot tub area.
A bathroom with a large mirror, a sink, and a towel rack.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
Room

5. 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.
€108
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A hotel room with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall.

6. Cozy Corner Motel

Cozy Corner Motel
Williamstown
  • Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
€79
includes taxes & fees
2 Nov - 3 Nov
Cozy Corner Motel
An indoor swimming pool with blue tiles, a wooden wall, and a blue and white color scheme.
A modern interior with a large window, a wooden table, and bar stools.
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.

7. 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.
€119
includes taxes & fees
1 Nov - 2 Nov
Hotel Downstreet, an Ascend Collection Hotel
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 house with a porch, snow-covered ground, and a Christmas tree with lights.

8. Maple Terrace Motel

Maple Terrace Motel
Williamstown
  • Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
€99
includes taxes & fees
1 Nov - 2 Nov
Maple Terrace Motel
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A motel with a parking lot, a swimming pool, and outdoor seating.
A bathroom with a bathtub, toilet, and shower.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.

9. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
€86
includes taxes & fees
12 Oct - 13 Oct
Berkshire Inn
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
€79
includes taxes & fees
18 Oct - 19 Oct
Howard Johnson by Wyndham Lenox
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.