A lake surrounded by autumn-colored trees and hills.

Cheshire Hotel with Pool

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Cheshire Hotel with Pool

Tonight
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

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.
HK$746
HK$920 total
includes taxes & fees
27 Sept - 28 Sept
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 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.

2. The Springs Motel

The Springs Motel
New Ashford
  • Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
HK$874
HK$958 total
includes taxes & fees
27 Sept - 28 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.
HK$847
HK$946 total
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
HK$624
HK$873 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A swimming pool with a diving board and a hot tub area.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

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.
HK$839
HK$938 total
includes taxes & fees
25 Oct - 26 Oct
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 interior with a large window, a wooden table, and bar stools.
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern bathroom with a large mirror, two sinks, a toilet, and towel racks.

6. 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.
HK$1,060
HK$1,184 total
includes taxes & fees
14 Oct - 15 Oct
Hotel Downstreet, an Ascend Collection Hotel
An outdoor seating area with Adirondack chairs and potted plants.
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.
A sign with the word "CLARM" on a grassy field with a road and trees in the background.

7. Cozy Corner Motel

Cozy Corner Motel
Williamstown
  • Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
HK$692
HK$813 total
includes taxes & fees
27 Sept - 28 Sept
Cozy Corner Motel
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A bathroom with a white sink, mirror, and toilet.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
HK$620
HK$692 total
includes taxes & fees
27 Sept - 28 Sept
Howard Johnson by Wyndham Lenox
A rectangular swimming pool with a blue interior, surrounded by a white picket fence.
A hay bale display with pumpkins and scarecrows.
A patio area with wooden chairs and tables, surrounded by dense greenery and trees.
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.
HK$812
HK$907 total
includes taxes & fees
27 Sept - 28 Sept
Willows Motel Williamstown
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A hotel room with a TV, desk, chair, lamp, and a bathroom with a sink and mirror.
A bathroom with a bathtub, toilet, and shower.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.

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.
HK$675
HK$753 total
includes taxes & fees
27 Sept - 28 Sept
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"If you want a perfect New England experience, this is the place. The hotel is amazing, it’s older so don’t think you’re going to walk into a modern place, but don’t let that deter you, the vibe is great! Will definitely stay here again."
Michelle 2-night trip
Posted less than an hour ago
The Red Lion Inn
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"Toilet was faulty but they gave us another room. Not much variety on the breakfast"
Ron 3-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Karl 1-night trip
Posted 3 days ago
Hotel Downstreet, an Ascend Collection Hotel
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 5 days ago
Jiminy Peak Mountain Resort
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 7 days ago
Howard Johnson by Wyndham Lenox

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.

Explore a world of travel with Expedia