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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

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Oct 17 - Oct 18
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Oct 18 - Oct 19
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Oct 23 - Oct 25
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Oct 30 - Nov 1

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.
$101 nightly
$112 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 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 hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

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 20 - Oct 21
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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.

3. 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.
$95 nightly
$106 total
Nov 17 - Nov 18
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$113 nightly
$126 total
Nov 16 - Nov 17
Total with taxes and fees
Berkshire Mountain Lodge
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 modern restaurant with wooden flooring, bar area, and seating arrangements.

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
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.

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.
$144 nightly
$160 total
Nov 2 - Nov 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A hotel room with a bed, a desk, a chair, and a carpeted floor.
A modern bathroom with a bathtub, shower, and handrails.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

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.
$110 nightly
$122 total
Nov 1 - Nov 2
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 modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A hotel patio with outdoor seating and a fire pit.
A modern reception area with a green textured wall, a reception desk, and a coffee machine.

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.
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
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.
$191 nightly
$214 total
Nov 4 - Nov 5
Total with taxes and fees
The Red Lion Inn
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.

10. 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.
$115 nightly
$128 total
Nov 11 - Nov 12
Total with taxes and fees
Vacation Village in the 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 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
$101 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
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
$95 nightly
$106 total
Nov 17 - Nov 18
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 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
$135 nightly
$150 total
Oct 20 - Oct 21
Total with taxes and fees
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.
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
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A hotel room with a bed, a desk, a chair, and a carpeted floor.
A room with a blue armchair, a wooden cabinet with a coffee maker, a television on the wall, and a small table with a cup.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
$110 nightly
$122 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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 hotel patio with outdoor seating and a fire pit.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A modern reception area with a green textured wall, a reception desk, and a coffee machine.

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 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.

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
$79 nightly
$88 total
Oct 18 - Oct 19
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.
An outdoor seating area with Adirondack chairs and a fire feature.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
$135 nightly
$151 total
Nov 8 - Nov 9
Total with taxes and fees
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 dining table set with a vase of flowers, a book, and cutlery.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.
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.

Brook Farm Inn

Brook Farm Inn
Lenox
$209 nightly
$237 total
Nov 2 - Nov 3
Total with taxes and fees
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
$383 nightly
$428 total
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
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 room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
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
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 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.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
$219 nightly
$245 total
Nov 15 - Nov 16
Total with taxes and fees
Hampton Terrace Inn
A two-story house with a brick entrance and a white facade.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
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
$393 nightly
$439 total
Nov 1 - Nov 2
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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
$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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 11 hours ago
The Red Lion Inn
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

8/10 Good
"Property was clean and in excellent shape overall. Pros: Food at the Bistro was excellent quality, and large portions. Room was clean and comfortable, slept well while staying there. Onsite laundry was a very helpful option and the washer and dryer, while expensive at $4.00 a load, were in excellent condition and did the job very well. Pool and hot tub were excellent. Cons: The light switches governing the various lights in the room were a little confusing at first. The free HBO had severe buffering issues, making watching anything on it tough. The controls for the automatic curtain open/shut were broken, making one start the open and shut manually. Overall, the Pros well outweighed the Cons."
William 2-night trip
Posted 18 hours ago
Courtyard by Marriott Lenox Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The hotel is in a good location. There are some good restaurants within walking distance. Only one complaint is that the bathroom fan is very loud."
Cynthia 3-night trip
Posted 20 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room and the hotel looked very clean, and the staff were very friendly. Also, the breakfast offered a good variety."
Luisa 1-night trip
Posted 1 day ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort

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