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Check availability on Chatham Hotels with Pool

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for Chatham hotels with a pool

1. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
  • Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
฿2,206
฿2,471 total
includes taxes & fees
22 Sept - 23 Sept
Berkshire Travel Lodge
An indoor swimming pool with a tiled floor, lounge chairs, a table, and potted plants.
A spacious living room with a stone fireplace, large windows, and modern furniture.
A spacious living area with a blue sofa, yellow armchair, and a coffee table. A staircase leads to an upper level with a balcony.
A spacious living area with a high ceiling, a staircase with a wooden railing, a large blue patterned rug, and a white sofa.

2. Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
Castleton-on-Hudson
  • Dive into refreshing bliss at this East Greenbush hotel's indoor pool, complete with cosy sun loungers for ultimate relaxation.
฿3,736
฿4,147 total
includes taxes & fees
27 Sept - 28 Sept
Comfort Inn & Suites East Greenbush - Albany
A hotel room with two beds, a desk, a TV, and a window with curtains.
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.
A hotel reception area with a check-in counter, a Holiday Inn Express sign, and a beverage refrigerator.

3. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
฿3,772
฿4,213 total
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 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.

4. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
฿4,985
฿5,568 total
includes taxes & fees
27 Sept - 28 Sept
The Yankee Inn
An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.
A spacious bedroom with a large bed, a wooden headboard, a bedside table with a book and a glass, and a window with curtains.
A spacious room with leather seating, large windows, and exposed brick walls.
A bar area with wooden beams, a bar counter, and stools.

5. Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
Hudson
฿7,350
฿9,788 total
includes taxes & fees
31 Aug - 1 Sept
Pocketbook Hotel and Bath
A backyard with a swimming pool, lounge chairs, and a hot tub.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
฿5,166
฿7,400 total
includes taxes & fees
8 Sept - 9 Sept
The Red Lion 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.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
฿3,103
฿4,198 total
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
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 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.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
฿2,582
฿2,884 total
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox
A large house with a balcony and a grassy yard.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A two-story building with a gabled roof and a chimney.

9. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
฿3,677
฿4,108 total
includes taxes & fees
1 Sept - 2 Sept
The Little Lion
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

10. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
฿4,050
฿4,523 total
includes taxes & fees
9 Sept - 10 Sept
Hampton Inn & Suites Berkshires-Lenox
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chatham Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Stacia 1-night trip
Posted 2 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great visit to Stockbridge. Can't think of a better place to stay than the iconic Red Lion Inn."
Daniel 2-night trip
Posted 17 hours ago
The Red Lion Inn
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"The experience and the comfort of the stay were appreciated."
George 2-night trip
Posted 1 day ago
Comfort Inn & Suites East Greenbush - Albany
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 6 days ago
Howard Johnson by Wyndham Lenox

Frequently asked questions

What are some accommodation options with pools in Chatham?
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. Country Inn & Suites by Radisson, Downtown Albany New York: Provides a seasonal outdoor pool, an indoor pool and buffet. The Yankee Inn: Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access. FairBridge Inn Express: Features 3 restaurants, an outdoor pool and spa services.
What is there to see and do in Chatham?
The picturesque settings of Kinderhook Lake and Queechy Lake showcase the area's natural beauty. Discover sights such as The Mac-Haydn Theatre during your stay.
When is the best time to book a hotel with a pool in Chatham?
Taking the local weather in Chatham into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chatham are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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