A historic building with a clock, a flag, and a street lamp.

Hotels with a Pool in Pittsfield

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Hotels with a Pool in Pittsfield

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

A garden with wooden Adirondack chairs and a stone pathway.

1. Berkshire Mountain Lodge

Pittsfield

Indoor pool
Hot tub

$95

$128 total

includes taxes & fees

Nov 22 - Nov 23

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

A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

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

2. Hilton Garden Inn Lenox Pittsfield

Pittsfield

Indoor pool

$128

$143 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

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

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

Pittsfield

Indoor pool
Hot tub

$99

$111 total

includes taxes & fees

Nov 22 - Nov 23

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

A fenced outdoor area with a pool, lounge chairs, and umbrellas.

A bathroom with a bathtub, toilet, and shower.

A motel with a parking lot, a swimming pool, and outdoor seating.

4. Berkshire Inn

Pittsfield

Pool
Free parking
Free WiFi
Air conditioning
24/7 front desk
Non-smoking

$86

$96 total

includes taxes & fees

Oct 25 - Oct 26

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A modern bathroom with a white bathtub, a showerhead, and a towel rack.

5. Hampton Inn & Suites Berkshires-Lenox

Lenox

Indoor pool
Pool loungers

$110

$122 total

includes taxes & fees

Oct 30 - Oct 31

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 glass-enclosed shower, a toilet, and a towel rack.

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

6. The Yankee Inn

Lenox

Outdoor pool
Indoor pool
Pool loungers
Hot tub

$106

$118 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.

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.

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

7. Howard Johnson by Wyndham Lenox

Lenox

Outdoor pool

$79

$88 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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

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

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

9. Element by Marriott Lenox Berkshires

Lenox

Indoor pool

$135

$151 total

includes taxes & fees

Nov 8 - Nov 9

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

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

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

10. Vacation Village in the Berkshires

Williamstown

Outdoor pool
Indoor pool
Pool umbrellas

$95

$117 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

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

11. 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 26 - Oct 27

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

A wooden cabin with a porch and steps leading to a door, surrounded by snow.

A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

12. Jiminy Peak Mountain Resort

Hancock

Outdoor pool
Pool loungers
2 hot tubs

$134

$150 total

includes taxes & fees

Oct 25 - Oct 26

An indoor swimming pool with clear lane markings, a poolside area with lounge chairs, and large windows allowing natural light.

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

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

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

13. 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 two Adirondack chairs and a small waterfall feature.

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

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

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.

14. 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 poolside area with lounge chairs, umbrellas, and a swimming pool.

A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

A cozy living room with a stone fireplace, comfortable seating, and a television.

A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

15. The Springs Motel

New Ashford

Pool
Pet friendly
Free parking
Free WiFi
Air conditioning

$106

$116 total

includes taxes & fees

Nov 1 - Nov 2

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

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

16. Brook Farm Inn

Lenox

Outdoor pool
Poolside bar

$205

$237 total

includes taxes & fees

Oct 26 - Oct 27

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 covered porch with wicker furniture and hanging flower baskets.

A bar with wooden floors and shelves filled with bottles.

17. The Red Lion Inn

Stockbridge

Outdoor pool
Pool loungers

$161

$230 total

includes taxes & fees

Nov 4 - Nov 5

18. Berkshire Travel Lodge

Austerlitz

Outdoor pool

$75

$84 total

includes taxes & fees

Oct 25 - Oct 26

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

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

19. The Little Lion

Great Barrington

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

$115

$128 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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

20. Sunset Inn

Lee

Near the beach

$81

$90 total

includes taxes & fees

Nov 2 - Nov 3

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Discover your perfect hotel with a pool in Pittsfield

Breakfast included

Hot tub

4 stars

Spa

5 stars

Top landmarks in Pittsfield

A snow-covered town with buildings, a ski lift, and a mountain in the background.

Bousquet Ski Area

8.2/10 (48 reviews)

Why not give yourself a treat with a trip to Bousquet Ski Area, one of the family attractions located 2.6 mi (4.3 km) from central Pittsfield. If you master the slopes, Jiminy Peak Mountain Resort is just a short drive away.

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A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Hancock Shaker Village

9.2/10 (101 reviews)

If seeing the sights is on your list of things to do, head to Hancock Shaker Village— just one of the landmarks located 4.7 mi (7.6 km) from central Pittsfield. You could also start your cultural experience by heading over to the museums in the area.

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A town with historic buildings, a prominent yellow church, and a mountainous backdrop.

Berkshire Museum

8.4/10 (26 reviews)

The center of Pittsfield is home to cultural attractions like Berkshire Museum, so you might want to stop by during your stay. If you want to experience more of the culture Pittsfield has to offer, head to Bousquet Ski Area, Lenox Mountain, and Hancock Shaker Village.

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Colonial Theater

8.0/10 (19 reviews)

If you’re after a show while in the center of Pittsfield, you might want to get tickets at Colonial Theater. If you enjoy the show and want to see another, Barrington Stage Company isn't far.

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Guido's Marketplace

9.6/10 (31 reviews)

If you like strolling among the stalls, you might want to head out to Guido's Marketplace when visiting Pittsfield.

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Barrington Stage Company

8.0/10 (16 reviews)

Barrington Stage Company is 0.4 mi (0.6 km) from central Pittsfield, why not stop by during your stay. If you enjoy the show and want to see another, Colonial Theater isn't far.

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Herman Melville's Arrowhead

8.2/10 (18 reviews)

If seeing the sights is on your list of things to do, head to Herman Melville's Arrowhead— just one of the landmarks located 2.3 mi (3.7 km) from central Pittsfield.

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Onota Lake

Onota Lake is 2.1 mi (3.4 km) from central Pittsfield, why not stop by during your stay.

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About the destination

If you're looking for a place to get away, look no further than Pittsfield. Whether you're planning to stay for a night or for the week, the area around Pittsfield has accommodations to fit every need. Search for hotels in Pittsfield with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Pittsfield hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Pittsfield hotel deals are here with our lowest price guarantee.