A mountainous landscape with a lake and dense forests.

Hotels with Swimming Pools in West Stockbridge

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Check availability on West Stockbridge Hotels with Swimming Pools

Tonight
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

Our top choices for West Stockbridge 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 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.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
S$224
includes taxes & fees
14 Sept - 15 Sept
The Yankee Inn
A backyard with a swimming pool, lounge chairs, and a hot tub.
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 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.
S$289
includes taxes & fees
14 Sept - 15 Sept
The Red Lion Inn
A large indoor swimming pool with clear water, surrounded by walls with informational posters and a reception area with a 'Welcome' sign.
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 hotel with balconies, a pond with rocks, and a clear sky.

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.
S$191
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
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, multiple seating areas, and a chandelier.

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
S$163
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
A spacious hotel lobby with multiple seating areas, large windows, and a television.

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.
S$185
includes taxes & fees
21 Sept - 22 Sept
Hampton Inn & Suites Berkshires-Lenox

6. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
  • Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
S$96
includes taxes & fees
25 Aug - 26 Aug
Berkshire Travel Lodge
An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern hotel lobby with seating areas, tables, and a reception desk.
A Holiday Inn Express & Suites building with a stone facade, a covered entrance, and a parking lot.

7. 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.
S$163
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A large house with a balcony and a grassy yard.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A two-story building with a gabled roof and a chimney.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

8. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
S$160
includes taxes & fees
2 Sept - 3 Sept
The Little Lion
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 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.

9. 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.
S$252
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Lenox Berkshires
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
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 bathroom with a white sink, mirror, and toilet.

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
S$112
includes taxes & fees
31 Aug - 1 Sept
Howard Johnson by Wyndham Lenox
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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

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 17 hours ago
Howard Johnson by Wyndham Lenox
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Everything was clean and well maintained. Very good included breakfast, close to Tanglewood, the Manor, the Norman Rockwell Museum, Lenox and Stockbridge."
Andrew 2-night trip
Posted 1 day ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Only real challenge—getting on the hotel wifi was a frustrating challenge! And every time you left your room you had to get on again."
Judith 4-night trip
Posted 1 day ago
Quality Inn Great Barrington
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"I had 2 rooms. 1 room (414) did not have a phone, the microwave didn't have power. The other room was fine. We didn't like that there was only 1 elevator working as we had to wait quite a while sometimes to go up or down. We understand that the hotel is undergoing renovations. Overall, we enjoyed our stay."
Frank 2-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We come up to the Berkshires every year for Tanglewood and always stay here. The rooms are always clean and the staff friendly and helpful. The rooms have either a full kitchen or kitchenette so at the very least you can have coffee when you wake-up. The fact that Vacation Village is on Brodie Mountain it's quiet and restful."
William 3-night trip
Posted 2 days ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"…."
Tiago 3-night trip
Posted 5 days ago
Jiminy Peak Mountain Resort
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

8/10 Good
"It was good place to stay over night for our plan. Friendly staff and clean room. Deer family are living near by, enjoy viewing them. It’s a old building, but nice quiet place."
Yoko 1-night trip
Posted 11 days ago
Pleasant Valley Motel West Stockbridge

Frequently asked questions

What are some accommodation options with pools in West Stockbridge?
Pleasant Valley Motel West Stockbridge: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Shaker Mill Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Vacation Village in the Berkshires: Features free self parking, an indoor pool and complimentary wireless Internet access. The Yankee Inn: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Berkshire Mountain Lodge: 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 Hotchkiss Mobile Studio. During your stay, visit sights such as Charles H. Baldwin & Sons, Ebenezer II Gifts and Antiques and Hoffman's Pottery. 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 19°C, while the coldest months are January and February, with an average of -3°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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