A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.

Hotels with a Pool in Stockbridge

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Hotels with a Pool in Stockbridge

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 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

$182

$253 total

includes taxes & fees

Oct 19 - Oct 20

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

A stone fountain surrounded by trees in a park setting.

2. The Inn at Stockbridge

Stockbridge

Pool
Free breakfast
Spa
Pet friendly
Free parking
Free WiFi

$438

$514 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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

Stockbridge

Pool loungers

$516

$625 total

includes taxes & fees

Oct 18 - Oct 19

A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.

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

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

A building with a porch and multiple windows, surrounded by purple flowers.

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

2 outdoor pools
2 indoor pools
Poolside bar
Pool loungers

$117

$150 total

includes taxes & fees

Oct 18 - Oct 19

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 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.

5. The Yankee Inn

Lenox

Outdoor pool
Indoor pool
Pool loungers
Hot tub

$108

$121 total

includes taxes & fees

Oct 27 - Oct 28

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

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

Great Barrington

Indoor pool

$119

$133 total

includes taxes & fees

Oct 19 - Oct 20

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 garden with wooden Adirondack chairs and a stone pathway.

7. Berkshire Mountain Lodge

Pittsfield

Indoor pool
Hot tub

$89

$121 total

includes taxes & fees

Oct 1 - Oct 2

A large house with a balcony and a grassy yard.

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.

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

$115

$128 total

includes taxes & fees

Oct 18 - Oct 19

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

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

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

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

9. Courtyard by Marriott Lenox Berkshires

Lenox

Indoor pool

$141

$158 total

includes taxes & fees

Oct 25 - Oct 26

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

Lenox

Indoor pool
Pool loungers

$122

$136 total

includes taxes & fees

Oct 20 - Oct 21

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.

11. Howard Johnson by Wyndham Lenox

Lenox

Outdoor pool

$79

$88 total

includes taxes & fees

Oct 1 - Oct 2

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

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

Great Barrington

Indoor pool

$195

$217 total

includes taxes & fees

Oct 4 - Oct 5

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

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

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.

13. Element by Marriott Lenox Berkshires

Lenox

Indoor pool

$169

$189 total

includes taxes & fees

Oct 18 - Oct 19

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

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

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

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

14. Hilton Garden Inn Lenox Pittsfield

Pittsfield

Indoor pool

$146

$163 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

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

15. Sunset Inn

Lee

Near the beach

$84

$94 total

includes taxes & fees

Oct 5 - Oct 6

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

A modern cafe with a counter, seating area, and large windows.

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

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Indoor pool
Hot tub

$106

$118 total

includes taxes & fees

Oct 29 - Oct 30

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.

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

17. Vacation Village in the Berkshires

Williamstown

Outdoor pool
Indoor pool
Pool umbrellas

$115

$139 total

includes taxes & fees

Oct 1 - Oct 2

A swimming pool with two Adirondack chairs and a small waterfall feature.

A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.

A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

A room with a grand piano, a chessboard, a horse statue, and a blue armchair.

18. Hampton Terrace Inn

Lenox

Pool
Free parking
Free WiFi
Air conditioning
Bar
Electric vehicle charging point

$254

$284 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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 house with a stone patio and wooden stools.

19. Little Cat Lodge

Copake Falls

Pool
Free breakfast
Free parking
Free WiFi
Restaurant
Air conditioning

$199

$223 total

includes taxes & fees

Oct 4 - Oct 5

A swimming pool with a diving board and a hot tub area.

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

A bathroom with a large mirror, a sink, and a towel rack.

20. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Indoor pool

$116

$130 total

includes taxes & fees

Oct 19 - Oct 20

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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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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 Lenox Library.

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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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Schantz Galleries

7.2/10 (5 reviews)

Art fans might want to browse the collections at Schantz Galleries in Stockbridge. If you want to see more of the art galleries in Stockbridge, Norman Rockwell Museum and Art et Industrie aren't far.

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About the destination

Spend time appreciating the historic sites, and checking out the bars in Stockbridge. Nature lovers can visit Naumkeag Museum and Berkshire Botanical Garden. And while you're here, be sure to stop by National Shrine of the Divine Mercy and Norman Rockwell Museum.