Hotels with a Pool in North Canaan

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Hotels with a Pool in North Canaan

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in North Canaan on Hotels.com. These North Canaan Hotels with a Pool consistently deliver on quality, location and traveler experience. Last updated on September 3, 2026.

An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.

A grand hallway with a chandelier, a staircase, and a table with flowers.

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.

1. Blackberry River Inn

Norfolk

Pool
Free breakfast
Free parking
Free WiFi
24/7 front desk

CNY1,008

CNY1,159 total

includes taxes & fees

Sep 10 - Sep 11

A modern hotel lobby with seating areas, tables, and a reception desk.

A hotel room with two beds, a desk, a TV, and a window with curtains.

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.

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Indoor pool

CNY746

CNY833 total

includes taxes & fees

Sep 7 - Sep 8

A backyard with a swimming pool, lounge chairs, and a hot tub.

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.

A bar with wooden floors and shelves filled with bottles.

3. The Red Lion Inn

Stockbridge

Outdoor pool
Pool loungers

CNY1,065

CNY1,523 total

includes taxes & fees

Sep 30 - Oct 1

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 sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

4. The Little Lion

Great Barrington

Pet friendly
Free parking
Free WiFi
Connecting rooms available
Air conditioning
Gym

CNY756

CNY845 total

includes taxes & fees

Sep 7 - Sep 8

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 hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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

Great Barrington

Indoor pool

CNY1,080

CNY1,206 total

includes taxes & fees

Sep 7 - Sep 8

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

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.

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

6. Little Cat Lodge

Copake Falls

Pool
Free breakfast
Free parking
Free WiFi
Restaurant
Air conditioning

CNY1,204

CNY1,349 total

includes taxes & fees

Sep 7 - Sep 8

A living room with a sofa, armchair, coffee table, and a patterned rug.

An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

A multi-story building with a balcony, a pond with rocks, and a tree.

7. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

2 outdoor pools
2 indoor pools
Poolside bar
Pool loungers

CNY690

CNY902 total

includes taxes & fees

Sep 7 - Sep 8

A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.

A modern hotel room with a bed, sofa, leather chair, and a small table.

A wooden deck with a swing chair and a bench overlooking a lake.

A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

8. Interlaken Inn & Resort

Lakeville

Full-service spa

CNY1,285

CNY1,478 total

includes taxes & fees

Sep 22 - Sep 23

A dining area with round tables set for two, a fireplace, and a mural on the wall.

A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

A white two-story house with a front door, windows, and a chimney.

9. The Old Inn On The Green

Great Barrington

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Restaurant

CNY2,218

CNY2,676 total

includes taxes & fees

Sep 7 - Sep 8

A swimming pool with a fenced area, lounge chairs, and a warning sign.

A hotel room with two beds, a chair, and a bedside table with a phone.

A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

10. Sunset Inn

Lee

Near the beach

CNY617

CNY689 total

includes taxes & fees

Sep 8 - Sep 9

A backyard with a swimming pool, surrounded by lush greenery and a wooden deck.

A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

A two-story building with a sign for Cornwall Inn, featuring a front porch and a mailbox.

A hotel room with a large bed, two bedside lamps, a chair, a small table, and a rug.

11. Cornwall Inn and Lodge

Cornwall Bridge

Pool loungers

CNY1,422

CNY1,635 total

includes taxes & fees

Sep 10 - Sep 11

A swimming pool with clear water, surrounded by a fence and trees.

A long wooden table with potted plants and candle holders in a modern interior setting.

A white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

A rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.

12. The Litchfield Inn

Litchfield

Full-service spa

CNY1,899

CNY2,184 total

includes taxes & fees

Sep 30 - Oct 1

A backyard with a swimming pool, surrounded by grass and trees.

A stone fountain surrounded by trees in a park setting.

13. The Inn at Stockbridge

Stockbridge

Pool
Free breakfast
Spa
Pet friendly
Free parking
Free WiFi

CNY2,534

CNY2,972 total

includes taxes & fees

Sep 13 - Sep 14

A poolside area with lounge chairs and a pool.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

14. Prospect Berkshires

Egremont

Outdoor pool
Pool loungers

CNY2,208

CNY2,691 total

includes taxes & fees

Sep 7 - Sep 8

A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

A neatly arranged bedroom with a bed, bedside table, and a dresser.

A two-story house with a brick entrance and a white facade.

15. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Pool loungers

A swimming pool with lounge chairs, surrounded by trees and a small building.

A large, two-story house with a well-maintained lawn and a fence.

A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

16. Devonfield Inn B&B

Lee

Outdoor pool
Pool loungers

CNY2,682

CNY2,995 total

includes taxes & fees

Sep 8 - Sep 9

A poolside area with lounge chairs and umbrellas, a pool, and a person relaxing.

A room with a hanging rattan chair, a wooden sofa, a small round table, and a ceiling fan. Large windows provide views of greenery outside.

A wooden deck with a railing, a cushioned chair, and a small table with a bottle and glass.

A stone building with a wooden staircase and a garden with white flowers.

17. Troutbeck

Amenia

Outdoor pool

CNY3,457

CNY4,180 total

includes taxes & fees

Sep 27 - Sep 28

A swimming pool with lounge chairs and umbrellas, surrounded by trees.

A modern house with a white exterior, two wooden doors, and a grey awning.

A large, two-story house with a wrap-around porch, a central entrance, and a flag.

A spacious living room with a large sectional sofa, a round coffee table, and a chandelier. There are large windows with curtains, a fireplace, and a view of greenery outside.

18. Belden House & Mews

Litchfield Historic District

Full-service spa

CNY3,394

CNY4,172 total

includes taxes & fees

Oct 4 - Oct 5

A backyard with a swimming pool, a fenced area, and a view of the surrounding forest and hills.

A backyard with a hot tub, outdoor seating, and a patio area.

A modern kitchen with white cabinetry, a wooden table, and a large window providing a view of the outdoors.

A spacious living area with a brick fireplace, a dining table with chairs, and a view of the outdoors.

19. Charming 6 Bdrm Countryside Stay

Great Barrington

Pool
Pet friendly
Free parking
Free WiFi
Air conditioning
Laundry facilities

CNY2,432

CNY6,076 total

includes taxes & fees

Sep 8 - Sep 9

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Discover your perfect hotel with a pool in North Canaan

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Hot tub

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Top landmarks in North Canaan

Land of Nod Vineyard and Winery

8.0/10 (1 review)

Travelers might want a tour of Land of Nod Vineyard and Winery, just one of the places to visit, and located 1.4 mi (2.3 km) from central North Canaan.

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North Canaan Town Hall

North Canaan Town Hall is worth a visit, located 0.8 mi (1.2 km) from central North Canaan.

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C H Pease Museum

If museums are on your list of things to see, then you might want to head to C H Pease Museum, located in the heart of Canann Village Historic District.If you want to see more of the museums in Canann Village Historic District, Ashley House isn't far either.

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Beckley Furnace Industrial Park

Beckley Furnace Industrial Park is 1.9 mi (3 km) from central North Canaan, why not stop by during your stay. Want to stretch your legs some more? Head to Edith Scoville Memorial Sanctuary and Lawrence Field, both nearby.

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Douglas Library

Douglas Library is worth a visit when in central Canann Village Historic District.

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Eddy Field

Eddy Field is 0.6 mi (1 km) from central North Canaan, why not stop by during your stay. Want to stretch your legs some more? Head to Lawrence Field and Edith Scoville Memorial Sanctuary, both nearby.

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Edith Scoville Memorial Sanctuary

If you like quiet time surrounded by flowers and greenery, then make a stop at Edith Scoville Memorial Sanctuary in the heart of North Canaan. Want to stretch your legs some more? Head to Lawrence Field, just a short walk away.

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Connecticut Railroad Historical Museum

If museums are on your list of things to see, then you might want to head to Connecticut Railroad Historical Museum, located in the heart of North Canaan.If you want to see more of the museums in North Canaan, Ashley House isn't far either.

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