A mountainous landscape with a lake and dense forests.

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Check availability on West Stockbridge Hotels with a Pool

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for West Stockbridge hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
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.
A covered porch with wicker furniture and hanging flower baskets.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
₩211,494
₩302,942 total
includes taxes & fees
Nov 15 - Nov 16
The Red Lion Inn
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.

2. 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.
₩168,650
₩188,382 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
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 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.

3. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₩142,438
₩159,103 total
includes taxes & fees
Nov 1 - Nov 2
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.

4. 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.
₩157,090
₩201,720 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Living area
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

5. 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.
₩147,222
₩164,447 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn & Suites Berkshires-Lenox
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 lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A hotel room with two beds, a desk, a television, and a dresser.

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.
₩192,872
₩215,437 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/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, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₩115,190
₩158,686 total
includes taxes & fees
Nov 9 - Nov 10
Berkshire Mountain Lodge
A swimming pool surrounded by a metal fence, with several lounge chairs and a small table nearby.
A dining table set with a vase of flowers, a book, and cutlery.
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.
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

8. Brook Farm Inn

Brook Farm Inn
Lenox
  • Dive into luxury poolside moments with a seasonal outdoor swimming area, vibrant bar service, and picturesque garden setting.
₩261,159
₩302,459 total
includes taxes & fees
Nov 15 - Nov 16
Brook Farm Inn
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.
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.

9. 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.
₩171,698
₩191,784 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Lenox Pittsfield
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.
A two-story house with a brick entrance and a white facade.

10. 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
  • Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
₩512,790
₩620,329 total
includes taxes & fees
Nov 11 - Nov 12
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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Choose what matters most at hotels with a pool in West Stockbridge

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top West Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Clean room. Special thank you to the cleaning and breakfast staff. Great balcony view. We will come back again."
Christopher 2-night trip
Posted 9 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"
Viviane 2-night trip
Posted 1 day ago
Vacation Village in the Berkshires
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

8/10 Good
"Older but well maintained, clean and had basic necessities. Very good for the price. Only problem was trying to adjust heat. Good hot shower. Would come again"
TIM 1-night trip
Posted 2 days ago
Pleasant Valley Motel West Stockbridge

Frequently asked questions

What are some accommodations with pools in West Stockbridge?
Shaker Mill Inn: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Pleasant Valley Motel West Stockbridge: Offers free self parking, an indoor pool, and complimentary wireless internet access. Vacation Village in the Berkshires: Offers a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Provides a steam room, 3 indoor pools, and spa services. Quality Inn Great Barrington: Offers 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in West Stockbridge?
Make a point to visit attractions like Stockbridge Bowl and Charles H. Baldwin & Sons. Discover sights such as Ebenezer II Gifts and Antiques and Hoffman's Pottery during your stay. The gardens and restaurants are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in West Stockbridge?
Taking into account the local weather in West Stockbridge is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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