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Chatham Hotel Guide - Hotels with Pool in Chatham, New York

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Check availability on Chatham Hotels with Pool

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Chatham hotels with a pool

Outdoor pool
Lobby sitting area
Exterior
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.
€67
includes taxes & fees
14 Oct - 15 Oct
Berkshire Travel Lodge
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

2. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
€106
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
An indoor swimming pool with a tiled floor, lounge chairs, a table, and potted plants.
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.
A spacious living room with a stone fireplace, large windows, and modern furniture.

3. 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.
€109
includes taxes & fees
10 Nov - 11 Nov
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 breakfast area with a counter, coffee machine, and a display of pastries.
A modern bathroom with a large mirror, a sink, and a shower.
A modern hotel lobby with seating areas, tables, and a reception desk.

4. 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.
€83
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern dining area with wooden tables and benches, green chairs, and pendant lighting.
A hotel lobby with orange rocking chairs, a reception desk, and a green carpet.
A compact living space with a kitchenette, a flat-screen TV, and a seating area.
A hotel room with a wooden desk, a television, a grey office chair, a sofa, and a window with curtains.

5. Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
West Coxsackie
€114
includes taxes & fees
1 Nov - 2 Nov
Spark by Hilton West Coxsackie
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A house with a stone patio and wooden stools.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

6. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
€153
includes taxes & fees
2 Nov - 3 Nov
Little Cat 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.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
€202
includes taxes & fees
3 Nov - 4 Nov
The Red Lion 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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
€79
includes taxes & fees
18 Oct - 19 Oct
Howard Johnson by Wyndham Lenox
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A building with a porch and multiple windows, surrounded by purple flowers.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.

9. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
€135
includes taxes & fees
28 Oct - 29 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
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.

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.
€103
includes taxes & fees
19 Oct - 20 Oct
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Amazing pool and great full kitchens in rooms."
robin 1-night trip
Posted 10 hours ago
Vacation Village in the Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"O"
Ilya 2-night trip
Posted 11 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

8/10 Good
"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"
Mark 1-night trip
Posted 11 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Beds were comfortable, room was clean, train was not often"
Patricia 3-night trip
Posted 13 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

8/10 Good
"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."
Patricia 1-night trip
Posted 19 hours ago
The Red Lion Inn
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

8/10 Good
"Good location and great for one night stopover"
Pamela 1-night trip
Posted 2 days ago
Comfort Inn Glenmont - Albany South

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 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 swimming pools and spa services.
What is there to see and do in Chatham?
The picturesque settings 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 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.