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The Berkshires Hotels with Swimming Pool

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Check availability on The Berkshires Hotels with Swimming Pools

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

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 modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
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.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
RM433
RM483 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
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 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.

2. 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 centre.
RM513
RM573 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
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 modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

3. 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.
RM586
RM655 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
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.

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.
RM478
RM613 total
includes taxes & fees
29 Oct - 30 Oct
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 spacious hotel lobby with multiple seating areas, large windows, and a television.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A modern bathroom with a wooden vanity, a toilet, and two framed pictures on the wall.

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.
RM448
RM500 total
includes taxes & fees
1 Nov - 2 Nov
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 modern hotel lobby with seating areas, tables, and a reception desk.
A breakfast area with a counter, coffee machine, and a display of pastries.
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.
RM339
RM379 total
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
RM350
RM482 total
includes taxes & fees
9 Nov - 10 Nov
Berkshire Mountain Lodge
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 reception area with a green textured wall, a reception desk, and a coffee machine.
A hotel patio with outdoor seating and a fire pit.

8. 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.
RM522
RM583 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
Indoor pool
A spacious living room with large windows, a fireplace, and a variety of seating options.
A spacious living room with a fireplace, comfortable seating, and 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.
RM328
RM411 total
includes taxes & fees
1 Nov - 2 Nov
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 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.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

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.
RM551
RM616 total
includes taxes & fees
8 Nov - 9 Nov
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 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.
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.

The Yankee Inn

The Yankee Inn
Lenox
RM433
RM483 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A snack bar with shelves of snacks and a refrigerated display.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern cafe with a counter, seating area, and large windows.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
RM404
RM451 total
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A building with a porch and multiple windows, surrounded by purple flowers.
A cafΓ© with a display case, a frozen food section, and a marketplace sign.
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
RM478
RM613 total
includes taxes & fees
29 Oct - 30 Oct
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 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 large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
RM513
RM573 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
Living area

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
RM448
RM500 total
includes taxes & fees
1 Nov - 2 Nov
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 modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
RM586
RM655 total
includes taxes & fees
2 Nov - 3 Nov
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 reception area with a green textured wall, a reception desk, and a coffee machine.
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
RM522
RM583 total
includes taxes & fees
1 Nov - 2 Nov
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 hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
RM323
RM360 total
includes taxes & fees
18 Oct - 19 Oct
Howard Johnson by Wyndham Lenox
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.
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.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
RM551
RM616 total
includes taxes & fees
8 Nov - 9 Nov
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 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 bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.
A dining table set with a vase of flowers, a book, and cutlery.

Brook Farm Inn

Brook Farm Inn
Lenox
RM794
RM920 total
includes taxes & fees
13 Nov - 14 Nov
Brook Farm Inn
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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
RM1,489
RM1,747 total
includes taxes & fees
12 Nov - 13 Nov
The Inn at Stockbridge
A dining area with round tables set for two, a fireplace, and a mural on the wall.
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.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
RM1,184
RM1,429 total
includes taxes & fees
15 Nov - 16 Nov
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 traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
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
RM894
RM998 total
includes taxes & fees
15 Nov - 16 Nov
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
RM1,559
RM1,886 total
includes taxes & fees
1 Nov - 2 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A park with a large tree, a bench, and a field of yellow flowers.
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 large, two-story house with a well-maintained lawn and a fence.

Devonfield Inn B&B

Devonfield Inn B&B
Lee
RM1,507
RM1,683 total
includes taxes & fees
5 Nov - 6 Nov
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 12 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
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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