A city street with buildings, parked cars, and solar panels.

Hotels with Pool & Resorts in Chatham from AU$105

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Check availability on Chatham Hotels with Pool

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

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.
AU$105
includes taxes & fees
2 Sept - 3 Sept
Berkshire Travel 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 spacious living room with a stone fireplace, large windows, and modern furniture.

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.
AU$176
includes taxes & fees
27 Sept - 28 Sept
Comfort Inn & Suites East Greenbush - Albany
A modern hotel lobby with seating areas, tables, and a reception desk.
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.
AU$179
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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
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.
AU$237
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 bar area with wooden beams, a bar counter, and stools.
A restaurant with long tables, chairs, and a brick wall.
A spacious room with leather seating, large windows, and exposed brick walls.

5. Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
Hudson
AU$414
includes taxes & fees
23 Sept - 24 Sept
Pocketbook Hotel and Bath
A backyard with a swimming pool, lounge chairs, and a hot tub.
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 bar with wooden floors and shelves filled with bottles.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
AU$303
includes taxes & fees
29 Sept - 30 Sept
The Red Lion Inn
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, seating area, and a bar.
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 spa pool experiences.
AU$179
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 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.
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.
AU$121
includes taxes & fees
8 Sept - 9 Sept
Howard Johnson by Wyndham Lenox
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.

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.
AU$171
includes taxes & fees
8 Sept - 9 Sept
The Little Lion
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
A spacious hotel lobby with multiple seating areas, large windows, and a television.

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.
AU$203
includes taxes & fees
8 Sept - 9 Sept
Hampton Inn & Suites Berkshires-Lenox
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
Spa pool
4 stars
5 stars
Spa

Top Chatham Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 13 hours ago
The Red Lion Inn
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 days ago
The Yankee Inn

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 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.

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