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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 6 - Oct 7
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Oct 7 - Oct 8
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Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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.
$106 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A building with a porch and multiple windows, surrounded by purple flowers.

2. 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.
$135 nightly
$150 total
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$115 nightly
$128 total
Nov 5 - Nov 6
Total with taxes and fees
Berkshire Mountain Lodge
An indoor swimming pool with clear lane markings, a poolside area with lounge chairs, and large windows allowing natural light.
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.
A modern hotel lobby with seating areas, tables, and a reception desk.

4. 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.
$95 nightly
$106 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 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.

5. 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.
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$191 nightly
$214 total
Nov 4 - Nov 5
Total with taxes and fees
The Red Lion Inn
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
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.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

7. 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.
$144 nightly
$160 total
Nov 2 - Nov 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

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.
$110 nightly
$123 total
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
Pool
Exterior
Bathroom shower
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

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.
$115 nightly
$128 total
Nov 4 - Nov 5
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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 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.
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
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 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
$106 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A building with a porch and multiple windows, surrounded by purple flowers.
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 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
$135 nightly
$150 total
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern hotel lobby with seating areas, tables, and a reception desk.
A kitchenette with a microwave, coffee maker, and coffee cups.
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.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
$95 nightly
$106 total
Nov 1 - Nov 2
Total with taxes and fees
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 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
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
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.
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
$144 nightly
$160 total
Nov 2 - Nov 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Pool
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.

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
$115 nightly
$128 total
Nov 4 - Nov 5
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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 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
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
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 gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
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
$79 nightly
$88 total
Oct 7 - Oct 8
Total with taxes and fees
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.
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
$151 nightly
$169 total
Nov 1 - Nov 2
Total with taxes and fees
Element by Marriott Lenox Berkshires
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 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
$319 nightly
$350 total
Nov 1 - Nov 2
Total with taxes and fees
The Old Inn On The Green
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4-star hotels with pools in The Berkshires

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 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
$319 nightly
$350 total
Nov 1 - Nov 2
Total with taxes and fees
The Old Inn On The Green
Front of property
Exterior
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
$383 nightly
$428 total
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
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 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
$376 nightly
$420 total
Nov 1 - Nov 2
Total with taxes and fees
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 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
$255 nightly
$285 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Terrace Inn
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 house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
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
$369 nightly
$412 total
Nov 2 - Nov 3
Total with taxes and fees
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Recommend hotel to provide breakfast and extend checkout time to 11 am."
Navaneeth 1-night trip
Posted 9 hours ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Beautiful location plenty of activities and very convenient having the country store on site! Also the onsite restaurant was amazing!"
Jeffrey 1-night trip
Posted 10 hours ago
Jiminy Peak Mountain Resort
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 14 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great staff, heated bathroom floors."
Ellen 3-night trip
Posted 18 hours ago
The Red Lion Inn

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