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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 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chatham hotels with a pool

A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₩142,076
₩158,699 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
Outdoor pool
Front of property
Exterior
Lobby sitting area

2. 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.
₩90,460
₩101,317 total
includes taxes & fees
Oct 6 - Oct 7
Berkshire Travel Lodge
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A hotel room with two beds, a desk, a television, and a dresser.

3. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
₩192,540
₩215,067 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with a tiled floor, lounge chairs, a table, and potted plants.
A spacious living area with a high ceiling, a staircase with a wooden railing, a large blue patterned rug, and a white sofa.
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 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.
₩152,665
₩169,459 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites East Greenbush - Albany
An indoor swimming pool with clear lane markings, a poolside area with lounge chairs, and large windows allowing natural light.
A modern bathroom with a large mirror, a sink, and a shower.
A breakfast area with a counter, coffee machine, and a display of pastries.
A modern hotel lobby with seating areas, tables, and a reception desk.

5. 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.
₩127,332
₩142,230 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

6. 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.
₩168,360
₩188,057 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.
A bar area with wooden beams, a bar counter, and stools.
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.

7. Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
Hudson
₩249,798
₩342,855 total
includes taxes & fees
Oct 26 - Oct 27
Pocketbook Hotel and Bath
Pool
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
Exterior

8. 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.
₩153,871
₩171,873 total
includes taxes & fees
Nov 4 - Nov 5
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

9. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₩114,901
₩158,287 total
includes taxes & fees
Oct 18 - Oct 19
Berkshire Mountain Lodge
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and flowers.
A circular outdoor fire pit with a metal rim, surrounded by gravel.
A residential garden with a pathway leading to a house.
A modern kitchen with white cabinetry, a built-in oven, and a coffee machine. There are shelves with glassware and a window providing natural light.

10. The Amelia

The Amelia
Hudson
  • Seasonal outdoor oasis awaits at The Amelia with loungers and umbrellas for perfect poolside relaxation.
₩408,133
₩461,191 total
includes taxes & fees
Oct 7 - Oct 8
The Amelia
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great staff, heated bathroom floors."
Ellen 3-night trip
Posted 3 hours ago
The Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Th property was beautiful and amongst the nature. The entire family had a good time in the pool, hot tub and the other kids amenities. The EV charging onsite was a plus"
Arabinda 1-night trip
Posted 16 hours ago
Vacation Village in the Berkshires

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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