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The Berkshires Hotels with Swimming Pool

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Check availability on The Berkshires Hotels with Swimming Pools

Tonight
31 Aug - 1 Sept
Tomorrow
1 Sept - 2 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

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 modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
RM348
RM389 total
includes taxes & fees
28 Sept - 29 Sept
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, seating area, and a bar.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
RM324
RM451 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A living room with a sofa, armchair, coffee table, and a patterned rug.
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.
A multi-story building with a symmetrical facade, multiple balconies, and a central tower.
A multi-story building with a balcony, a pond with rocks, and a tree.

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.
RM471
RM605 total
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
A backyard with a swimming pool, lounge chairs, and a hot tub.
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 large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

4. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
RM634
RM908 total
includes taxes & fees
29 Sept - 30 Sept
The Red Lion Inn
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.
A spacious living room with large windows, a fireplace, and a variety of seating options.

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.
RM389
RM479 total
includes taxes & fees
2 Sept - 3 Sept
Vacation Village in the Berkshires
A modern hotel lobby with seating areas, tables, and a reception desk.
A hotel room with two beds, a desk, a TV, and a window with curtains.
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

6. 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.
RM463
RM517 total
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
A spacious hotel lobby with multiple seating areas, large windows, and a television.

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.
RM500
RM558 total
includes taxes & fees
13 Sept - 14 Sept
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A hotel room with two beds, a desk, a television, and a dresser.
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.

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.
RM647
RM722 total
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with blue tiles, a wooden wall, and a blue and white color scheme.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A modern bathroom with a large mirror, two sinks, a toilet, and towel racks.
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.
RM596
RM666 total
includes taxes & fees
1 Oct - 2 Oct
Hotel Downstreet, an Ascend Collection Hotel
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
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 covered outdoor area with stone pillars and a view of a road and green hills.

10. 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.
RM715
RM799 total
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Lenox 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 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 swimming pool with a surrounding deck, a stone wall, and a building in the background.

The Yankee Inn

The Yankee Inn
Lenox
RM348
RM389 total
includes taxes & fees
28 Sept - 29 Sept
The Yankee Inn
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 multi-story building with a symmetrical facade, multiple balconies, and a central tower.
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
RM471
RM605 total
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
A modern hotel lobby with seating areas, tables, and a reception desk.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
RM463
RM517 total
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.
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
RM500
RM558 total
includes taxes & fees
13 Sept - 14 Sept
Hampton Inn & Suites Berkshires-Lenox
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."
A hallway with a collection of plates on the walls, leading to a staircase.
Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
North Adams
RM721
RM895 total
includes taxes & fees
8 Sept - 9 Sept
The Porches Inn at Mass MoCA
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, a sofa, a coffee station, and a TV mounted on the wall.

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
RM318
RM355 total
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
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
RM647
RM722 total
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A covered outdoor area with stone pillars and a view of a road and green hills.

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
RM715
RM799 total
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Lenox Berkshires
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 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.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
RM716
RM800 total
includes taxes & fees
7 Sept - 8 Sept
Element by Marriott Lenox Berkshires
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 modern cafe with a wooden accent wall, a coffee machine, and black chairs.
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
RM596
RM666 total
includes taxes & fees
1 Oct - 2 Oct
Hotel Downstreet, an Ascend Collection Hotel
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4-star hotels with pools in The Berkshires

A two-story house with a brick entrance and a white facade.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
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.

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
RM1,329
RM1,608 total
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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
RM1,517
RM1,780 total
includes taxes & fees
13 Sept - 14 Sept
The Inn at Stockbridge
A large, two-story house with a well-maintained lawn and a fence.
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.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

Devonfield Inn B&B

Devonfield Inn B&B
Lee
RM1,566
RM1,749 total
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
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 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
RM1,283
RM1,548 total
includes taxes & fees
1 Sept - 2 Sept
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 dining room with a large table set for a meal, surrounded by ornate chairs.
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
RM1,027
RM1,147 total
includes taxes & fees
13 Sept - 14 Sept
Hampton Terrace Inn
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"This facility appeared to be brand new. Breakfast was excellent and the dining area was spacious and attractive. We would definitely recommend this hotel and will stay here again when we are back in the area!"
Cathy 1-night trip
Posted 14 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Nice to have a kitchenette to cook in"
Jacqueline 1-night trip
Posted 17 hours ago
Jiminy Peak Mountain Resort
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 2 days ago
The Red Lion Inn

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