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 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.

1. The Red Lion Inn

Stockbridge

Outdoor pool
Pool loungers

$161

$230 total

includes taxes & fees

Nov 4 - Nov 5

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

$365

$428 total

includes taxes & fees

Nov 12 - Nov 13

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.

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

Stockbridge

Pool loungers

$382

$462 total

includes taxes & fees

Nov 7 - Nov 8

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

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

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

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

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

South Lee

2 outdoor pools
2 indoor pools
Poolside bar
Pool loungers

$117

$150 total

includes taxes & fees

Oct 27 - Oct 28

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

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

A modern bathroom with a large mirror, a sink, and a shower.

A breakfast bar with a variety of food options including cereal, fruit, and yogurt.

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

Great Barrington

Indoor pool

$90

$101 total

includes taxes & fees

Nov 12 - Nov 13

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

Two Adirondack chairs facing a river with a forested hill in the background.

6. The Yankee Inn

Lenox

Outdoor pool
Indoor pool
Pool loungers
Hot tub

$106

$118 total

includes taxes & fees

Nov 1 - Nov 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 bathroom with a toilet, a shower with glass doors, and a towel rack with towels.

7. The Little Lion

Great Barrington

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

$115

$128 total

includes taxes & fees

Oct 26 - Oct 27

A hotel room with a wooden desk, a flat-screen TV, a coffee maker, a blue chair, and a lamp.

A spacious hotel lobby with multiple seating areas, large windows, and a television.

8. Hampton Inn & Suites Berkshires-Lenox

Lenox

Indoor pool
Pool loungers

$110

$122 total

includes taxes & fees

Oct 31 - Nov 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.

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

Great Barrington

Indoor pool

$144

$160 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

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

10. Courtyard by Marriott Lenox Berkshires

Lenox

Indoor pool

$126

$140 total

includes taxes & fees

Nov 1 - Nov 2

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.

11. Devonfield Inn B&B

Lee

Outdoor pool
Pool loungers

$369

$412 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

12. Element by Marriott Lenox Berkshires

Lenox

Indoor pool

$135

$151 total

includes taxes & fees

Nov 8 - Nov 9

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

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A garden with wooden Adirondack chairs and a stone pathway.

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

13. Berkshire Mountain Lodge

Pittsfield

Indoor pool
Hot tub

$95

$128 total

includes taxes & fees

Nov 24 - Nov 25

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

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

A dining table set with a vase of flowers, a book, and cutlery.

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.

14. Brook Farm Inn

Lenox

Outdoor pool
Poolside bar

$195

$225 total

includes taxes & fees

Oct 26 - Oct 27

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

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

15. Sunset Inn

Lee

Near the beach

$81

$90 total

includes taxes & fees

Nov 1 - Nov 2

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 restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

16. Hilton Garden Inn Lenox Pittsfield

Pittsfield

Indoor pool

$119

$133 total

includes taxes & fees

Nov 15 - Nov 16

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

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

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.

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

Pittsfield

Indoor pool
Hot tub

$95

$106 total

includes taxes & fees

Nov 24 - Nov 25

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

A bathroom with a bathtub, a sink, and a mirror. There is a bottle of champagne and two glasses on the counter.

18. Hampton Terrace Inn

Lenox

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

$219

$245 total

includes taxes & fees

Nov 17 - Nov 18

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.

19. Howard Johnson by Wyndham Lenox

Lenox

Outdoor pool

$79

$88 total

includes taxes & fees

Oct 26 - Oct 27

A poolside area with lounge chairs and a pool.

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

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

A wooden table with a green chair and a yellow vase with flowers.

20. Prospect Berkshires

Egremont

Outdoor pool
Pool loungers

$284

$350 total

includes taxes & fees

Nov 9 - Nov 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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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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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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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.