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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 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Chatham hotels with a pool

Outdoor pool
Exterior
Lobby sitting area
Front of property

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 25 - Oct 26
Total with taxes and fees
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 hotel with a covered entrance, stone facade, and arched windows.
A spacious living area with a blue sofa, yellow armchair, and a coffee table. A staircase leads to an upper level with a balcony.

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 cozy sun loungers for ultimate relaxation.
$110 nightly
$122 total
Nov 12 - Nov 13
Total with taxes and fees
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 hotel room with two beds, a desk, a TV, and a window with curtains.
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.

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.
$90 nightly
$101 total
Nov 12 - Nov 13
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.
A spacious hotel lobby with multiple seating areas, large windows, and a television.

4. 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.
$110 nightly
$122 total
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.

5. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$101 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
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 hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

6. 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 25 - Oct 26
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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 spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$110 nightly
$123 total
Nov 22 - Nov 23
Total with taxes and fees
Berkshire Mountain Lodge
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
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.
A covered porch with wicker furniture and hanging flower baskets.

8. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$191 nightly
$214 total
Nov 17 - Nov 18
Total with taxes and fees
The Red Lion Inn
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 room with leather seating, large windows, and exposed brick walls.
A restaurant with long tables, chairs, and a brick wall.

9. Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
Hudson
$300 nightly
$339 total
Nov 15 - Nov 16
Total with taxes and fees
Pocketbook Hotel and Bath
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

10. 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 25 - Oct 26
Total with taxes and fees
The Little Lion
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"clean. local walking distances to everything,"
robert 2-night trip
Posted less than an hour ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"I loved this property. Nice room with fireplace and balcony, great shower, good breakfast, easy parking, and beautiful walking trail behind the hotel."
Barry 2-night trip
Posted 2 hours ago
The Yankee Inn
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Check in & out were easy. Mint restaurant was GREAT. View from the balcony overlooking the lake was super. Same weekend for the last four years & we will be back."
Garry 2-night trip
Posted 6 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Great stay"
barbara 1-night trip
Posted 1 day ago
Comfort Inn & Suites East Greenbush - Albany
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

10/10 Excellent
";"
Jake 1-night trip
Posted 7 days ago
Comfort Inn Glenmont - Albany South

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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