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Find Hotels with a Pool in The Berkshires, MA

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Check availability on The Berkshires Hotels with a Pool

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
￥16,759
￥18,720 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 hotel room with two beds, a desk, a television, and a dresser.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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.
￥22,708
￥25,365 total
includes taxes & fees
Nov 3 - Nov 4
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 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.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

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.
￥19,856
￥22,179 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard by Marriott Lenox Berkshires
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
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.
A building with a porch and multiple windows, surrounded by purple flowers.

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.
￥18,495
￥23,749 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 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.
A hotel patio with outdoor seating and a fire pit.

5. 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.
￥20,218
￥22,583 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 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.

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
￥13,678
￥18,810 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Mountain Lodge
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 modern hotel with a large entrance, multiple floors, and a well-lit facade.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
￥15,652
￥17,483 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Indoor pool
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.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

8. 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.
￥12,701
￥15,921 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A hotel room with a bed, a desk, a chair, and a carpeted floor.
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern bathroom with a bathtub, shower, and handrails.

9. 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.
￥17,333
￥19,361 total
includes taxes & fees
Nov 3 - Nov 4
Hampton Inn & Suites Berkshires-Lenox
A swimming pool surrounded by a metal fence, with several lounge chairs and a small table nearby.
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.
A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

10. Brook Farm Inn

Brook Farm Inn
Lenox
  • Dive into luxury poolside moments with a seasonal outdoor swimming area, vibrant bar service, and picturesque garden setting.
￥30,752
￥35,615 total
includes taxes & fees
Nov 2 - Nov 3
Brook Farm Inn
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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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
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.

The Yankee Inn

The Yankee Inn
Lenox
￥16,759
￥18,720 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 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.
A snack bar with shelves of snacks and a refrigerated display.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
￥15,652
￥17,483 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 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.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
￥18,495
￥23,749 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 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.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
￥19,856
￥22,179 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A hotel room with a bed, a desk, a chair, and a carpeted floor.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A room with a blue armchair, a wooden cabinet with a coffee maker, a television on the wall, and a small table with a cup.

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
￥17,333
￥19,361 total
includes taxes & fees
Nov 3 - Nov 4
Hampton Inn & Suites Berkshires-Lenox
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
￥22,708
￥25,365 total
includes taxes & fees
Nov 3 - Nov 4
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
￥20,218
￥22,583 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 featuring a table and chairs, a kitchenette with a coffee machine, and a television 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, a sofa, a coffee station, and a TV mounted on the wall.

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
￥12,488
￥13,949 total
includes taxes & fees
Oct 19 - Oct 20
Howard Johnson by Wyndham Lenox
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.
An outdoor seating area with Adirondack chairs and a fire feature.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
￥21,344
￥23,842 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 cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.
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.

Brook Farm Inn

Brook Farm Inn
Lenox
￥30,752
￥35,615 total
includes taxes & fees
Nov 2 - Nov 3
Brook Farm Inn
View all properties

4-star hotels with pools in The Berkshires

Front of property
A stone fountain surrounded by trees in a park setting.
Exterior
A living room with a fireplace, leather sofas, and a dog.

The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
￥57,672
￥67,640 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 room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
A white two-story house with a front door, windows, and a chimney.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
￥45,843
￥55,318 total
includes taxes & fees
Nov 1 - Nov 2
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 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.
A dining room with a large table set for a meal, surrounded by ornate chairs.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
￥34,608
￥38,657 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Terrace Inn
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.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

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
￥54,344
￥65,741 total
includes taxes & fees
Nov 6 - Nov 7
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 house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
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 bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

Devonfield Inn B&B

Devonfield Inn B&B
Lee
￥58,339
￥65,164 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
"Would be nice if they offered breakfast as part of accommodations. Pool and jacuzzi nice."
Matt 1-night trip
Posted less than an hour ago
Courtyard by Marriott Lenox Berkshires
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"The staff was very helpful. The were lots of activities offered including the pool, hot tub, movie theater , and renting movies for free. The unit was very spacious and comfortable. We could hear the people above us stomping around a bit but that’s to be expected."
Jessica 1-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Good stay"
Jared 1-night trip
Posted 2 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Location is great as it’s close to downtown and was clean and staff was lovely. Was just a little more expensive than I expected it to be."
regina 1-night trip
Posted 4 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room and the hotel looked very clean, and the staff were very friendly. Also, the breakfast offered a good variety."
Luisa 1-night trip
Posted 5 hours ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort

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