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Hotels with Swimming Pools in The Berkshires

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Check availability on The Berkshires Hotels with Swimming Pools

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 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 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.
S$154
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
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.
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.
S$202
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Lenox Berkshires
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.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
S$142
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 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.

4. 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.
S$192
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 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.
A modern cafe with a counter, seating area, and large windows.

5. 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.
S$151
includes taxes & fees
29 Oct - 30 Oct
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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.

6. 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.
S$278
includes taxes & fees
7 Oct - 8 Oct
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Pool
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
Bathroom shower

7. 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.
S$172
includes taxes & fees
20 Oct - 21 Oct
Hampton Inn & Suites Berkshires-Lenox
Indoor pool
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with a fireplace, comfortable seating, and large windows.
A spacious living room with large windows, a fireplace, and a variety of seating options.

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.
S$150
includes taxes & fees
30 Sept - 1 Oct
Vacation Village in the Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A bar with wooden floors and shelves filled with bottles.

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
S$309
includes taxes & fees
19 Oct - 20 Oct
The Red Lion Inn
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 bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
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.
S$209
includes taxes & fees
25 Oct - 26 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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

The Yankee Inn

The Yankee Inn
Lenox
S$154
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn
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 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.

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
S$192
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 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
S$278
includes taxes & fees
7 Oct - 8 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
S$170
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.
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 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
S$202
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.
Exterior
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
S$172
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 interior with a large window, a wooden table, and bar stools.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A modern hotel building with the name "Hotel Downtown" on the facade.

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
S$193
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 large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
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
S$209
includes taxes & fees
25 Oct - 26 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, a sofa, a coffee station, and a TV mounted 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.

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
S$113
includes taxes & fees
30 Sept - 1 Oct
Howard Johnson by Wyndham Lenox
Room
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.
A conference room with a whiteboard, tables, and chairs.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
S$147
includes taxes & fees
29 Oct - 30 Oct
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 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 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
S$584
includes taxes & fees
25 Oct - 26 Oct
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.
Exterior

The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
S$656
includes taxes & fees
30 Sept - 1 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 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
S$798
includes taxes & fees
12 Oct - 13 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 dining room with a large table set for a meal, surrounded by ornate chairs.
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.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
S$366
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 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
S$509
includes taxes & fees
8 Oct - 9 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 20 hours ago
Quality Inn Great Barrington
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 1 day 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 1 day 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

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