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
25 Aug - 26 Aug
Tomorrow
26 Aug - 27 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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 spacious living room with large windows, a fireplace, and a variety of seating options.
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$137
includes taxes & fees
31 Aug - 1 Sept
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 bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
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.
S$166
includes taxes & fees
9 Sept - 10 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 freestanding bathtub, a fireplace, and two framed posters on the wall.
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.

3. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
S$224
includes taxes & fees
21 Sept - 22 Sept
The Yankee Inn
An indoor swimming pool with clear water, surrounded by white lounge chairs and a tiled deck.
A banquet hall with round tables set for a formal event, featuring white tablecloths, silverware, and floral centerpieces.
A modern bar area with a central island, multiple bar stools, and a seating area with tables and chairs.

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$169
includes taxes & fees
22 Sept - 23 Sept
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 reception area with a large landscape painting, a dark reception desk, and a potted plant.

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.
S$211
includes taxes & fees
2 Sept - 3 Sept
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 building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A covered porch with beige siding, white railings, and a row of wooden benches.

6. Cozy Corner Motel

Cozy Corner Motel
Williamstown
  • Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
S$132
includes taxes & fees
9 Sept - 10 Sept
Cozy Corner Motel
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 hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.

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.
S$147
includes taxes & fees
26 Aug - 27 Aug
Willows Motel Williamstown
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A garden with wooden Adirondack chairs and a stone pathway.
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.
S$162
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
A swimming pool with a wooden deck, lounge chairs, and umbrellas.
A wooden cabin with a covered deck, a fire pit, and string lights.
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.

9. Huttopia Berkshires

Huttopia Berkshires
Williamstown
  • Forest serenity and mountain trails define this Berkshires campground, complete with refreshing pool.
S$138
includes taxes & fees
23 Sept - 24 Sept
Huttopia Berkshires
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 hotel room with a TV, desk, chair, lamp, and a bathroom with a sink and mirror.
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.
S$128
includes taxes & fees
27 Aug - 28 Aug
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 Yankee Inn

The Yankee Inn

8/10 Good
"Almost two hotels in one. Several structures. One nicely updated, all check-ins, breakfast. Our stay was in an older building… while it was clean there was a musty smell. The room was very dated and the ac was loud… Time to upgrade that building."
Barb 1-night trip
Posted less than an hour ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"BIen situé avec pleins de restaurants accessibe à pied autour. Grand parking sécuritaire en face il y a la caserne de pompiers. Idéalement ce serait bien d'installer des bornes électriques de recharge pour les véhicules électriques. Déjeuner modeste. Pas de protéines. Pâtisseries et fruits bons. Très propre. Personnel courtois"
Cynthia 2-night trip
Posted 19 hours ago
Hotel Downstreet, an Ascend Collection Hotel
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 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 4 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. 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 high-speed (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 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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