A person snowboarding down a snowy slope.

Find Hotels with a Pool in The Berkshires, MA

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Hotels with a Pool

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
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.

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 building with a porch and multiple windows, surrounded by purple flowers.
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.

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 hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$116 nightly
$129 total
Oct 22 - Oct 23
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 modern bathroom with a large mirror, a sink, and a shower.
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.

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.
$102 nightly
$114 total
Oct 25 - Oct 26
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 covered outdoor area with stone pillars and a view of a road and green hills.

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
Indoor pool
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with large windows, a fireplace, and a variety of seating options.
A spacious living room with a fireplace, comfortable seating, and large windows.

6. 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
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A hotel with a brick facade, a covered entrance, and an American flag.
Exterior

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.
$114 nightly
$127 total
Nov 7 - Nov 8
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel room with two beds, a desk, a television, and a dresser.

8. 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 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.

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$198 nightly
$222 total
Nov 4 - Nov 5
Total with taxes and fees
The Red Lion Inn
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A bathroom with a white sink, mirror, and toilet.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$79 nightly
$88 total
Oct 8 - Oct 9
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
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.

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 hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
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 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 coffee station with two coffee machines and a variety of coffee pods and cups.
A kitchenette with a microwave, coffee maker, and coffee cups.
A breakfast area with a counter, coffee machine, and a display of pastries.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
$102 nightly
$114 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A lobby with seating areas, a reception desk, and a bar.
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.
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 Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
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
$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.
A hotel with a brick facade, a covered entrance, and an American flag.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
Exterior

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
$114 nightly
$127 total
Nov 7 - Nov 8
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 spacious living room with a large sofa, a coffee table, and a fireplace.
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.

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 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
$79 nightly
$88 total
Oct 8 - Oct 9
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 reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
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 5 - Nov 6
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 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
$319 nightly
$350 total
Nov 1 - Nov 2
Total with taxes and fees
The Old Inn On The Green
View all properties

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 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
$319 nightly
$350 total
Nov 1 - Nov 2
Total with taxes and fees
The Old Inn On The Green
Front of property
A stone fountain surrounded by trees in a park setting.
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
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 two-story house with a brick entrance and a white facade.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
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
$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 dining room with a large table set for a meal, surrounded by ornate chairs.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
$242 nightly
$270 total
Nov 2 - Nov 3
Total with taxes and fees
Hampton Terrace Inn
A large, two-story house with a well-maintained lawn and a fence.
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.
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.
View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"
Rohit 1-night trip
Posted 14 hours ago
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great stay, very clean, super comfortable beds. Will def stay again when in the area."
Julia 2-night trip
Posted 14 hours ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 15 hours ago
The Red Lion Inn
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 2 days 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 2 days ago
Quality Inn Great Barrington

Explore a world of travel with Expedia