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Hotels with Swimming Pool in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Swimming Pool

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for The Berkshires hotels with a pool

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.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P6,666
P7,446 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
P9,033
P10,090 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 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.

3. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
P7,899
P8,823 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
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 Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
P7,347
P9,435 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A modern bathroom with a wooden vanity, a toilet, and two framed pictures on the wall.
Living area
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

5. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
P6,886
P7,692 total
includes taxes & fees
Nov 13 - Nov 14
Hampton Inn & Suites Berkshires-Lenox
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 hotel lobby with seating areas, tables, and a reception desk.
A modern bathroom with a large mirror, a sink, and a shower.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
P5,597
P6,252 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A hotel patio with outdoor seating and a fire pit.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
  • Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
P8,042
P8,982 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
P5,391
P7,426 total
includes taxes & fees
Nov 9 - Nov 10
Berkshire Mountain Lodge
Indoor pool
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.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
P5,045
P6,325 total
includes taxes & fees
Nov 12 - Nov 13
Vacation Village in the Berkshires
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 modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

10. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
  • Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
P8,489
P9,483 total
includes taxes & fees
Nov 8 - Nov 9
Element by Marriott Lenox Berkshires
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Choose what matters most at hotels with a pool in The Berkshires

Breakfast included
4 stars
5 stars
Hot tub
Spa

Hotels with pools and free breakfast in The Berkshires

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
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.

The Yankee Inn

The Yankee Inn
Lenox
P6,666
P7,446 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
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 reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
P6,217
P6,945 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
P7,347
P9,435 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
P7,899
P8,823 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Living area
A bed with a white pillow and a nightstand with a modern lamp.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
P6,886
P7,692 total
includes taxes & fees
Nov 13 - Nov 14
Hampton Inn & Suites Berkshires-Lenox
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.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
P9,033
P10,090 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A hotel patio with outdoor seating and a fire pit.
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 modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
P8,042
P8,982 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
P4,961
P5,542 total
includes taxes & fees
Oct 18 - Oct 19
Howard Johnson by Wyndham Lenox
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
An outdoor seating area with Adirondack chairs and a fire feature.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
P8,489
P9,483 total
includes taxes & fees
Nov 8 - Nov 9
Element by Marriott Lenox Berkshires
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.
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 cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

Brook Farm Inn

Brook Farm Inn
Lenox
P12,215
P14,147 total
includes taxes & fees
Nov 13 - Nov 14
Brook Farm Inn
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4-star hotels with pools in The Berkshires

Front of property
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
A stone fountain surrounded by trees in a park setting.
A living room with a fireplace, leather sofas, and a dog.

The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
P22,939
P26,904 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Stockbridge
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 cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
P18,212
P21,976 total
includes taxes & fees
Nov 2 - Nov 3
The Old Inn On The Green
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 dining room with a large table set for a meal, surrounded by ornate chairs.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
P14,250
P15,917 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Terrace Inn
A two-story house with a brick entrance and a white facade.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
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.

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
P23,984
P29,014 total
includes taxes & fees
Nov 4 - Nov 5
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large, two-story house with a well-maintained lawn and a fence.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

Devonfield Inn B&B

Devonfield Inn B&B
Lee
P23,173
P25,884 total
includes taxes & fees
Nov 2 - Nov 3
Devonfield Inn B&B
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top The Berkshires Hotel Reviews

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Sitting around the fire pit after a long day of leaf peeping was glorious..."
Steve 2-night trip
Posted 13 hours ago
Courtyard by Marriott Lenox Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Clean room. Special thank you to the cleaning and breakfast staff. Great balcony view. We will come back again."
Christopher 2-night trip
Posted 19 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"good location, friendly helpful staff"
Scott Patterson 6-night trip
Posted 19 hours ago
Quality Inn Great Barrington
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"
Viviane 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Our room was nice and clean. The suite is perfect. Can fix a cup of tea or a meal, everything you need just bring your food. A restaurant on site if you don't want to cook. Bed was comfortable with crisp white linens."
Anna 2-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

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