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The Berkshires Hotel Guide - Hotels with Pool in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Pool

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 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.
€83
includes taxes & fees
28 Sept - 29 Sept
The Yankee Inn
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 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.
€97
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
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.
€130
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.
€195
includes taxes & fees
29 Sept - 30 Sept
The Red Lion Inn
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 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.
€103
includes taxes & fees
1 Sept - 2 Sept
Vacation Village in the Berkshires
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.
A hotel reception area with a check-in counter, a Holiday Inn Express sign, and a beverage refrigerator.

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.
€111
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.

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.
€119
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 lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
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.

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.
€155
includes taxes & fees
8 Sept - 9 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 modern interior with a large window, a wooden table, and bar stools.
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.
€143
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 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.

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.
€171
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 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
€83
includes taxes & fees
28 Sept - 29 Sept
The Yankee Inn
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.
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
€130
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
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.
A hotel reception area with a check-in counter, a Holiday Inn Express sign, and a beverage refrigerator.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
€111
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
€119
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 cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.
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
€192
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 hotel room with a dining area, a sofa, a coffee station, and a TV mounted 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
€76
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 hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
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.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
€155
includes taxes & fees
8 Sept - 9 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.
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
€171
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 reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
An outdoor seating area with Adirondack chairs and a fire feature.
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
€172
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 hotel building with the name "Hotel Downtown" on the facade.
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
€143
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 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.

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
€345
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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
€382
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 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 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
€375
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 white two-story house with a front door, windows, and a chimney.

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
€332
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 traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
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.

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
€214
includes taxes & fees
21 Sept - 22 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 12 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 15 hours ago
Jiminy Peak Mountain Resort
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Location"
patricia 2-night trip
Posted 2 days ago
Quality Inn Great Barrington
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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