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Find Hotels with a Pool in Chatham, NY

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Check availability on Chatham Hotels with a Pool

Tonight
Oct 2 - Oct 3
Tomorrow
Oct 3 - Oct 4
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Chatham hotels with a pool

Outdoor pool
Exterior
Lobby sitting area
Lobby sitting area

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.
$75 nightly
$84 total
Oct 5 - Oct 6
Total with taxes and fees
Berkshire Travel Lodge
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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

2. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$106 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$111 nightly
$124 total
Nov 2 - Nov 3
Total with taxes and fees
Berkshire Mountain Lodge
An indoor swimming pool with a tiled floor, lounge chairs, a table, and potted plants.
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.
A hotel with a covered entrance, stone facade, and arched windows.

4. 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 cozy sun loungers for ultimate relaxation.
$114 nightly
$126 total
Nov 1 - Nov 2
Total with taxes and fees
Comfort Inn & Suites East Greenbush - Albany
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 hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

5. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$79 nightly
$88 total
Oct 4 - Oct 5
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Indoor pool
A spacious living room with large windows, a fireplace, and a variety of seating options.
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.

6. 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.
$110 nightly
$123 total
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$196 nightly
$219 total
Nov 2 - Nov 3
Total with taxes and fees
The Red Lion Inn
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.

8. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
$115 nightly
$128 total
Oct 18 - Oct 19
Total with taxes and fees
The Little Lion
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

9. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Pool
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
Exterior
Bathroom shower

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.
$116 nightly
$129 total
Nov 3 - Nov 4
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chatham Hotel Reviews

Frequently asked questions

What are some accommodations 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 free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Hotel located near Albany Medical Center. Offers full, an indoor pool, and free self parking. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Offers a seasonal outdoor pool, an indoor pool, and buffet. Comfort Inn Glenmont - Albany South: Provides a steam room, 3 indoor pools, and spa services.
What is there to see and do in Chatham?
The picturesque setting of Art Omi International Arts Center - Fields Sculpture Park and Kinderhook 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 into account the local weather in Chatham can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Chatham are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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