A mountainous landscape with a lake and dense forests.

West Stockbridge Hotels with Swimming Pool

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Check availability on West Stockbridge Hotels with Swimming Pools

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for West Stockbridge hotels with a pool

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 large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

1. 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.
RM513
RM573 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
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 large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.

2. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
RM643
RM921 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A backyard with a swimming pool, surrounded by grass and trees.
A stone fountain surrounded by trees in a park setting.
Exterior
A modern bathroom with a black marble shower, gold fixtures, and a tiled floor.

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
  • Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
RM1,489
RM1,747 total
includes taxes & fees
12 Nov - 13 Nov
The Inn at Stockbridge
A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

4. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
  • Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
RM551
RM616 total
includes taxes & fees
8 Nov - 9 Nov
Element by Marriott Lenox Berkshires
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
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.
A building with a porch and multiple windows, surrounded by purple flowers.

5. 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.
RM478
RM613 total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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 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.

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
RM433
RM483 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
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 neatly arranged bedroom with a bed, bedside table, and a dresser.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

7. 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.
RM1,559
RM1,886 total
includes taxes & fees
4 Nov - 5 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A swimming pool surrounded by a metal fence, with several lounge chairs and a small table nearby.
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 cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

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.
RM794
RM920 total
includes taxes & fees
27 Oct - 28 Oct
Brook Farm Inn
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A modern bathroom with a white bathtub, a showerhead, and a towel rack.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

9. 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.
RM448
RM500 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Berkshires-Lenox
A swimming pool with two Adirondack chairs and a small waterfall feature.
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 bathroom with a bathtub, a sink, and a mirror. There is a bottle of champagne and two glasses on the counter.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

10. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
  • Seasonal outdoor pool, tennis courts, and garden grounds create a refreshing retreat at this Tanglewood hotel.
RM894
RM998 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Terrace Inn
View all properties

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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I needed to stay here for work. Hotel met and exceeded all my needs."
Matthew 1-night trip
Posted 1 hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

8/10 Good
"Efficient & comfortable. Very good value."
brian 1-night trip
Posted 2 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This is hands down my favorite hotel, and I have stayed here before and will keep coming back again and again! Everything about this place makes it feel special. The rooms are always spotless, incredibly spacious, and equipped with everything you need to feel right at home. Having a coffee maker, a full-size refrigerator, an oven, and a stove makes such a difference, especially for longer stays. The excellent jacuzzi is another big plus and makes it easy to relax and unwind. The property also has so many great amenities, and the surrounding nature is absolutely beautiful. There are plenty of amazing places to explore nearby, making it a perfect destination for a relaxing getaway while still having lots of things to do. What I love most is that the rooms feel more like a fully equipped apartment than a typical hotel room. It’s the kind of place where you can truly settle in, feel comfortable, and wish you could stay longer. I absolutely love this hotel, and it will always be one of my favorite places to stay. I will definitely be back again and again!"
Diana 1-night trip
Posted 5 hours ago
Vacation Village in the Berkshires
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

10/10 Excellent
"O"
Joe 1-night trip
Posted 2 days ago
Pleasant Valley Motel West Stockbridge

Frequently asked questions

What are some accommodation options 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 swimming 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 such as 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 the local weather in West Stockbridge into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19Β°C, while the coldest months are January and February, with an average of -3Β°C. The snowiest months in West Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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