Hotels with a Pool in Stockbridge

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Hotels with a Pool in Stockbridge

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Stockbridge on Hotels.com. These Stockbridge Hotels with a Pool consistently deliver on quality, location and traveler experience. Last updated on September 8, 2026.

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

A bar with wooden floors and shelves filled with bottles.

A covered porch with wicker furniture and hanging flower baskets.

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

1. The Red Lion Inn

Stockbridge

Outdoor pool
Pool loungers

CNY1,063

CNY1,521 total

includes taxes & fees

Sep 30 - Oct 1

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

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

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

A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

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

Stockbridge

Pool loungers

CNY2,216

CNY2,680 total

includes taxes & fees

Sep 28 - Sep 29

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

A stone fountain surrounded by trees in a park setting.

A modern bathroom with a black marble shower, gold fixtures, and a tiled floor.

3. The Inn at Stockbridge

Stockbridge

Pool
Free breakfast
Spa
Pet friendly
Free parking
Free WiFi

CNY2,530

CNY2,967 total

includes taxes & fees

Sep 15 - Sep 16

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 hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

2 outdoor pools
2 indoor pools
Poolside bar
Pool loungers

CNY688

CNY900 total

includes taxes & fees

Sep 14 - Sep 15

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

Lenox

Outdoor pool
Indoor pool
Pool loungers
Hot tub

CNY778

CNY869 total

includes taxes & fees

Sep 22 - Sep 23

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

A breakfast area with a counter, coffee machine, and a display of pastries.

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

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

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

Great Barrington

Indoor pool

CNY886

CNY989 total

includes taxes & fees

Sep 15 - Sep 16

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A spacious lobby with a fireplace, seating area, and a bar.

A garden with wooden Adirondack chairs and a stone pathway.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

7. Berkshire Mountain Lodge

Pittsfield

Indoor pool
Hot tub

CNY534

CNY747 total

includes taxes & fees

Oct 1 - Oct 2

A large house with a balcony and a grassy yard.

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

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

A two-story building with a gabled roof and a chimney.

8. The Little Lion

Great Barrington

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

CNY755

CNY843 total

includes taxes & fees

Sep 9 - Sep 10

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.

9. Hampton Inn & Suites Berkshires-Lenox

Lenox

Indoor pool
Pool loungers

CNY862

CNY963 total

includes taxes & fees

Sep 30 - Oct 1

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A hotel room with two beds, a desk, a television, and a dresser.

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

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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

Great Barrington

Indoor pool

CNY1,268

CNY1,417 total

includes taxes & fees

Sep 9 - Sep 10

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

A spacious living room with a large sofa, a coffee table, and a fireplace.

A hotel patio with outdoor seating and a fire pit.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

11. Hilton Garden Inn Lenox Pittsfield

Pittsfield

Indoor pool

CNY982

CNY1,096 total

includes taxes & fees

Sep 13 - Sep 14

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 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.

12. Howard Johnson by Wyndham Lenox

Lenox

Outdoor pool

CNY530

CNY592 total

includes taxes & fees

Sep 9 - Sep 10

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 standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

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

13. Sunset Inn

Lee

Near the beach

CNY616

CNY688 total

includes taxes & fees

Sep 9 - Sep 10

A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

14. Element by Marriott Lenox Berkshires

Lenox

Indoor pool

CNY1,309

CNY1,462 total

includes taxes & fees

Sep 15 - Sep 16

A hot tub area with a pool, lounge chairs, and a caution sign.

A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

15. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Indoor pool

CNY792

CNY884 total

includes taxes & fees

Sep 13 - Sep 14

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.

16. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Indoor pool
Hot tub

CNY850

CNY949 total

includes taxes & fees

Sep 10 - Sep 11

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A covered outdoor area with stone pillars and a view of a road and green hills.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

17. Courtyard by Marriott Lenox Berkshires

Lenox

Indoor pool

CNY1,306

CNY1,459 total

includes taxes & fees

Sep 13 - Sep 14

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

A spacious living room with a fireplace, comfortable seating, and large windows.

A spacious living room with large windows, a fireplace, and a variety of seating options.

18. Vacation Village in the Berkshires

Williamstown

Outdoor pool
Indoor pool
Pool umbrellas

CNY638

CNY787 total

includes taxes & fees

Sep 15 - Sep 16

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

A house with a stone patio and wooden stools.

19. Little Cat Lodge

Copake Falls

Pool
Free breakfast
Free parking
Free WiFi
Restaurant
Air conditioning

CNY1,202

CNY1,346 total

includes taxes & fees

Sep 9 - Sep 10

A swimming pool surrounded by a metal fence, with several lounge chairs and a small table nearby.

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

20. Brook Farm Inn

Lenox

Outdoor pool
Poolside bar

CNY1,484

CNY1,712 total

includes taxes & fees

Sep 9 - Sep 10

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Discover your perfect hotel with a pool in Stockbridge

Breakfast included

Hot tub

4 stars

Spa

5 stars

Top landmarks in Stockbridge

Norman Rockwell Museum

9.4/10 (347 reviews)

Norman Rockwell Museum is 0.8 mi (1.2 km) from central Stockbridge, why not stop by during your stay. If you want to experience more of the culture Stockbridge has to offer, head to Berkshire Botanical Garden, Naumkeag Museum, and National Shrine of the Divine Mercy.

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National Shrine of the Divine Mercy

9.0/10 (83 reviews)

If seeing the sights is on your list of things to do, head to National Shrine of the Divine Mercy— just one of the landmarks located 0.5 mi (0.8 km) from central Stockbridge.

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Naumkeag Museum

9.4/10 (10 reviews)

If museums are on your list of things to see, then you might want to head to Naumkeag Museum, located in the heart of Stockbridge.If you want to see more of the museums in Stockbridge, you can easily walk to Mission House.

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Berkshire Botanical Garden

9.4/10 (14 reviews)

Ready for an education in local botany? Berkshire Botanical Garden should make your list of places to visit, located 1.2 mi (2 km) from central Stockbridge. Want to stretch your legs some more? Head to Naumkeag Museum and The Mount, both nearby.

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Stockbridge Bowl

Check out the water views and take some great vacation pics at Stockbridge Bowl in Stockbridge.

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Berkshire Theatre Festival

8.8/10 (3 reviews)

Berkshire Theatre Festival is 0.9 mi (1.5 km) from central Stockbridge, why not stop by during your stay. If you enjoy the show and want to see another, Shakespeare and Company and Tanglewood Music Center are both not far.

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Frelinghuysen Morris House and Studio

8.2/10 (10 reviews)

Frelinghuysen Morris House and Studio is 4.4 mi (7 km) from central Stockbridge, why not stop by during your stay. If you want to experience more of the culture Stockbridge has to offer, head to Tanglewood Music Center, Shakespeare and Company, and The Mount.

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Mission House

9.6/10 (5 reviews)

If museums are on your list of things to see in Stockbridge, then you might want to head to Mission House. If you want to see more of the museums in Stockbridge, Norman Rockwell Museum and Animagic Museum of Animation aren't far.

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Keep exploring

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