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
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Cheshire hotels with a pool

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.

1. 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.
P7,481
P8,357 total
includes taxes & fees
Nov 1 - Nov 2
Hotel Downstreet, an Ascend Collection Hotel
Indoor pool
A spacious living room with a fireplace, comfortable seating, and large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

2. 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.
P5,043
P6,321 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
An indoor swimming pool with clear water, a diving area, and a view of the outdoors through large windows.
A modern living room with a fireplace, comfortable seating, a flat-screen TV, and a stone accent wall.
A fire feature with a metal frame and a brick wall in the background.
A Fairfield Inn & Suites by Marriott hotel with a brick facade, large windows, and a covered outdoor seating area.

3. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
Williamstown
  • Swim indoors year-round at this welcoming retreat with an indoor pool, hot tub, and extended pool hours for ultimate relaxation.
P9,549
P10,667 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Williamstown
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A patio area with outdoor furniture, a fire pit, and potted plants.
A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
A cozy living room with a stone fireplace, comfortable seating, and a television.

4. The Springs Motel

The Springs Motel
New Ashford
  • Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
P6,990
P7,668 total
includes taxes & fees
Nov 4 - Nov 5
The Springs Motel
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
A hallway with a collection of plates on the walls, leading to a staircase.
A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.
A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

5. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
North Adams
  • Float peacefully day or night at this 24-hour outdoor pool and hot tub sanctuary.
P10,367
P12,982 total
includes taxes & fees
Nov 8 - Nov 9
The Porches Inn at Mass MoCA
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P6,653
P7,431 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
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 restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

7. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
  • Ski-in/ski-out mountain resort with refreshing pool, hot tubs, and tennis courts awaits.
P8,417
P9,401 total
includes taxes & fees
Oct 18 - Oct 19
Jiminy Peak Mountain Resort
A rectangular swimming pool with a blue interior, surrounded by a white picket fence.
A patio area with wooden chairs and tables, surrounded by dense greenery and trees.
A hay bale display with pumpkins and scarecrows.
A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.

8. 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.
P5,307
P5,927 total
includes taxes & fees
Nov 1 - Nov 2
Willows Motel Williamstown
A swimming pool with a diving board and a hot tub area.
A bathroom with a large mirror, a sink, and a towel rack.
Room
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

9. 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.
P6,151
P6,870 total
includes taxes & fees
Nov 6 - Nov 7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A swimming pool with lounge chairs and a fence.
A breakfast buffet setup with cereal, milk, juice, and pastries.
A house with a porch, snow-covered ground, and a Christmas tree with lights.
A garden with a wooden pergola, potted plants, and a lawn with chairs.

10. Maple Terrace Motel

Maple Terrace Motel
Williamstown
  • Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
P6,214
P6,940 total
includes taxes & fees
Nov 3 - Nov 4
Maple Terrace 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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."
Mark 1-night trip
Posted 12 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"
Rohit 1-night trip
Posted 2 days ago
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great stay, very clean, super comfortable beds. Will def stay again when in the area."
Julia 2-night trip
Posted 2 days 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 2 days ago
The Red Lion Inn

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. 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 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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