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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
30 Sep - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 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 glass-enclosed shower, a toilet, and a towel rack.
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.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
SAR 406
SAR 453 total
includes taxes & fees
27 Oct - 28 Oct
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, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
SAR 299
SAR 418 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
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.

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.
SAR 439
SAR 564 total
includes taxes & fees
18 Oct - 19 Oct
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 reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

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.
SAR 398
SAR 445 total
includes taxes & fees
29 Oct - 30 Oct
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Indoor pool
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A spacious living room with a fireplace, comfortable seating, and large windows.

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.
SAR 366
SAR 451 total
includes taxes & fees
4 Oct - 5 Oct
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 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.

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.
SAR 531
SAR 593 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Lenox Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
SAR 641
SAR 902 total
includes taxes & fees
19 Oct - 20 Oct
The Red Lion Inn
Pool
Bathroom shower
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Exterior

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.
SAR 458
SAR 511 total
includes taxes & fees
20 Oct - 21 Oct
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.
SAR 507
SAR 567 total
includes taxes & fees
14 Oct - 15 Oct
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 hotel patio with outdoor seating and a fire pit.
A spacious living room with a large sofa, a coffee table, and a fireplace.

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.
SAR 549
SAR 614 total
includes taxes & fees
4 Oct - 5 Oct
Hilton Garden Inn Lenox Pittsfield
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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 swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.

The Yankee Inn

The Yankee Inn
Lenox
SAR 406
SAR 453 total
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn
A building with a porch and multiple windows, surrounded by purple flowers.
A café 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

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
SAR 439
SAR 564 total
includes taxes & fees
18 Oct - 19 Oct
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 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 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
SAR 731
SAR 816 total
includes taxes & fees
4 Oct - 5 Oct
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 hotel room with two beds, a desk, a TV, and a window with curtains.
A coffee station with two coffee machines and a variety of coffee pods and cups.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
SAR 447
SAR 499 total
includes taxes & fees
19 Oct - 20 Oct
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 modern restaurant with wooden flooring, bar area, and seating arrangements.
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
SAR 531
SAR 593 total
includes taxes & fees
25 Oct - 26 Oct
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.
Exterior
Pool

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
SAR 458
SAR 511 total
includes taxes & fees
20 Oct - 21 Oct
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
SAR 507
SAR 567 total
includes taxes & fees
14 Oct - 15 Oct
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 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.

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
SAR 549
SAR 614 total
includes taxes & fees
4 Oct - 5 Oct
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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
SAR 297
SAR 331 total
includes taxes & fees
1 Oct - 2 Oct
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
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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4-star hotels with pools in The Berkshires

A large, two-story house with a well-maintained lawn and a fence.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
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 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
SAR 1,536
SAR 1,715 total
includes taxes & fees
25 Oct - 26 Oct
Devonfield Inn B&B
Front of property
A living room with a fireplace, leather sofas, and a dog.
Exterior
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
SAR 1,645
SAR 1,929 total
includes taxes & fees
1 Oct - 2 Oct
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 cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A neatly arranged bedroom with a bed, bedside table, and a dresser.

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
SAR 1,939
SAR 2,346 total
includes taxes & fees
18 Oct - 19 Oct
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
SAR 954
SAR 1,066 total
includes taxes & fees
29 Oct - 30 Oct
Hampton Terrace Inn
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 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
SAR 1,239
SAR 1,495 total
includes taxes & fees
1 Oct - 2 Oct
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.
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Top The Berkshires Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 2 days ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice room. Exceptionally clean. Great staff"
Daniel 3-night trip
Posted 2 days 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 7 days ago
Hotel Downstreet, an Ascend Collection Hotel
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 11 days ago
Howard Johnson by Wyndham Lenox