A building with a marquee sign reading "MAHAIWE Performing Arts Center" and a smaller sign for "Black Violin" performances.

Hotels with a Pool in Great Barrington

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Hotels with a Pool in Great Barrington

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 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.

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

Great Barrington

Indoor pool

$95

$106 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

Great Barrington

Indoor pool

$144

$160 total

includes taxes & fees

Nov 2 - Nov 3

A large house with a balcony and a grassy yard.

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

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

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

3. 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

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 cabin with a bed, a chair, and a table by a large window overlooking a lake.

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

4. Prospect Berkshires

Egremont

Outdoor pool
Pool loungers

$345

$419 total

includes taxes & fees

Nov 2 - Nov 3

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

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

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

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

5. The Old Inn On The Green

Great Barrington

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Restaurant

$290

$350 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

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

South Lee

2 outdoor pools
2 indoor pools
Poolside bar
Pool loungers

$112

$144 total

includes taxes & fees

Oct 8 - Oct 9

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

A house with a stone patio and wooden stools.

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.

7. Little Cat Lodge

Copake Falls

Pool
Free breakfast
Free parking
Free WiFi
Restaurant
Air conditioning

$169

$189 total

includes taxes & fees

Nov 2 - Nov 3

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

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

A bar with wooden floors and shelves filled with bottles.

A covered porch with wicker furniture and hanging flower baskets.

8. The Red Lion Inn

Stockbridge

Outdoor pool
Pool loungers

$161

$230 total

includes taxes & fees

Nov 3 - Nov 4

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 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.

9. The Yankee Inn

Lenox

Outdoor pool
Indoor pool
Pool loungers
Hot tub

$106

$118 total

includes taxes & fees

Nov 1 - Nov 2

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

10. Courtyard by Marriott Lenox Berkshires

Lenox

Indoor pool

$126

$140 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

11. Element by Marriott Lenox Berkshires

Lenox

Indoor pool

$151

$169 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

12. Sunset Inn

Lee

Near the beach

$84

$94 total

includes taxes & fees

Oct 7 - Oct 8

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

13. Berkshire Mountain Lodge

Pittsfield

Indoor pool
Hot tub

$95

$128 total

includes taxes & fees

Nov 4 - Nov 5

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 dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

14. Blackberry River Inn

Norfolk

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

$150

$173 total

includes taxes & fees

Oct 18 - Oct 19

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.

15. Hampton Inn & Suites Berkshires-Lenox

Lenox

Indoor pool
Pool loungers

$115

$128 total

includes taxes & fees

Nov 4 - Nov 5

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 gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

16. Howard Johnson by Wyndham Lenox

Lenox

Outdoor pool

$79

$88 total

includes taxes & fees

Oct 7 - Oct 8

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 a counter, seating area, and large windows.

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

Pittsfield

Indoor pool
Hot tub

$103

$115 total

includes taxes & fees

Nov 4 - Nov 5

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

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

18. The Inn at Stockbridge

Stockbridge

Pool
Free breakfast
Spa
Pet friendly
Free parking
Free WiFi

$365

$428 total

includes taxes & fees

Nov 1 - Nov 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 neatly arranged bedroom with a bed, bedside table, and a dresser.

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

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

Stockbridge

Pool loungers

$382

$462 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 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.

A hotel patio with outdoor seating and a fire pit.

20. Hilton Garden Inn Lenox Pittsfield

Pittsfield

Indoor pool

$128

$143 total

includes taxes & fees

Nov 1 - Nov 2

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Discover your perfect hotel with a pool in Great Barrington

Breakfast included

Hot tub

4 stars

Spa

5 stars

Top landmarks in Great Barrington

Lake Mansfield Park

9.0/10 (22 reviews)

Lake Mansfield Park is 0.7 mi (1.1 km) from central Great Barrington, why not stop by during your stay. If you like Lake Mansfield Park, you'll love Naumkeag Museum and Berkshire Botanical Garden, both just a short drive away.

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Ski Butternut

9.0/10 (134 reviews)

Ski the fall line at Ski Butternut located 2.3 mi (3.7 km) from central Great Barrington. If you master the slopes, Catamount Ski Area is just a short drive away.

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Mahaiwe Performing Arts Center

9.0/10 (22 reviews)

Mahaiwe Performing Arts Center is in the heart of Great Barrington, so why not stop by during your stay. If you'd also like to explore some of the parks in Great Barrington, Lake Mansfield Park and Thom Reed UFO Monument Park are both nearby.

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Lake Buel

8.8/10 (23 reviews)

Lake Buel is 4.8 mi (7.7 km) from central Great Barrington, why not stop by during your stay.

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Housatonic River Walk

9.2/10 (76 reviews)

Housatonic River Walk is in the heart of Great Barrington, so why not stop by during your stay.

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Monument Mountain

Monument Mountain is just one of the landmarks located 3.1 mi (5 km) from central Great Barrington, so you might want to stop by for a few pics during your trip.

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W.E.B. Du Bois Boyhood Homesite

8.8/10 (29 reviews)

W.E.B. Du Bois Boyhood Homesite is just one of the landmarks located 2.1 mi (3.3 km) from central Great Barrington, so you might want to stop by for a few pics during your trip.

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Jug End State Reservation

8.8/10 (3 reviews)

Jug End State Reservation is 2.1 mi (3.3 km) from central Egremont, why not stop by during your stay.

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About the destination

Spend time appreciating the live music, and checking out the local cuisine in Great Barrington. If you're visiting during colder months, enjoy activities such as skiing during your stay. Learn about the local heritage of Great Barrington at landmarks like Mahaiwe Performing Arts Center and W.E.B. Du Bois Boyhood Homesite. Check out other sights like Housatonic River Walk and Housatonic River.