A person snowboarding down a snowy slope.

Find Hotels with a Pool in The Berkshires, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Hotels with a Pool

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 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.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₩146,240
₩163,355 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, seating area, and a bar.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₩107,784
₩150,645 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
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 living room with a sofa, armchair, coffee table, and a patterned rug.
A building with a porch and multiple windows, surrounded by purple flowers.

3. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
₩158,426
₩203,435 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Club Vacations Oak 'n Spruce Resort
An indoor swimming pool with clear water, tiled floors, and a blue wall.
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.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

4. 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.
₩144,006
₩160,854 total
includes taxes & fees
Oct 29 - Oct 30
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.

5. 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.
₩128,831
₩158,758 total
includes taxes & fees
Sep 30 - Oct 1
Vacation Village in the 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 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.

6. 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.
₩192,113
₩214,589 total
includes taxes & fees
Oct 25 - Oct 26
Courtyard by Marriott Lenox Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
₩241,495
₩337,244 total
includes taxes & fees
Oct 19 - Oct 20
The Red Lion Inn
Pool
Bathroom shower
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
A spacious hotel lobby with multiple seating areas, large windows, and a television.

8. 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.
₩163,220
₩182,317 total
includes taxes & fees
Oct 20 - Oct 21
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with blue tiles, a wooden wall, and a blue and white color scheme.
A modern bathroom with a large mirror, two sinks, a toilet, and towel racks.
A modern interior with a large window, a wooden table, and bar stools.
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

9. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
  • Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
₩183,003
₩204,414 total
includes taxes & fees
Oct 14 - Oct 15
Hotel Downstreet, an Ascend Collection Hotel
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 bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

10. 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.
₩198,729
₩221,987 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Lenox Pittsfield
View all properties

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 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.

The Yankee Inn

The Yankee Inn
Lenox
₩146,240
₩163,355 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
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 café with a display case, a frozen food section, and a marketplace sign.
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

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
₩158,426
₩203,435 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Club Vacations Oak 'n Spruce Resort
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.
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.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
₩263,570
₩294,408 total
includes taxes & fees
Oct 4 - Oct 5
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern hotel lobby with seating areas, tables, and a reception desk.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A kitchenette with a microwave, coffee maker, and coffee cups.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
₩161,134
₩179,983 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 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.

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
₩192,113
₩214,589 total
includes taxes & fees
Oct 25 - Oct 26
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
Exterior

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
₩163,220
₩182,317 total
includes taxes & fees
Oct 20 - Oct 21
Hampton Inn & Suites Berkshires-Lenox
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern cafe with a wooden accent wall, a coffee machine, and black chairs.
A modern hotel building with the name "Hotel Downtown" on the facade.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
₩183,003
₩204,414 total
includes taxes & fees
Oct 14 - Oct 15
Hotel Downstreet, an Ascend Collection Hotel
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
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 bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
₩198,729
₩221,987 total
includes taxes & fees
Oct 25 - Oct 26
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
₩106,972
₩119,489 total
includes taxes & fees
Oct 4 - Oct 5
Howard Johnson by Wyndham Lenox
Room
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
₩139,931
₩156,302 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Inn & Suites Pittsfield-Berkshires by IHG
View all properties

4-star hotels with pools in The Berkshires

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 bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Devonfield Inn B&B
Lee
₩555,647
₩620,654 total
includes taxes & fees
Oct 25 - Oct 26
Devonfield Inn B&B
Front of property
A stone fountain surrounded by trees in a park setting.
A living room with a fireplace, leather sofas, and a dog.
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.

The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
₩593,056
₩695,560 total
includes taxes & fees
Oct 1 - Oct 2
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
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
₩701,650
₩848,804 total
includes taxes & fees
Oct 12 - Oct 13
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
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.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
₩348,196
₩388,939 total
includes taxes & fees
Oct 29 - Oct 30
Hampton Terrace Inn
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 cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
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
₩446,843
₩539,204 total
includes taxes & fees
Oct 5 - Oct 6
The Old Inn On The Green
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.
View all properties

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 19 hours ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice room. Exceptionally clean. Great staff"
Daniel 3-night trip
Posted 19 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Karl 1-night trip
Posted 6 days ago
Hotel Downstreet, an Ascend Collection Hotel
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 8 days ago
Jiminy Peak Mountain Resort
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 10 days ago
Howard Johnson by Wyndham Lenox

Explore a world of travel with Expedia