A mountainous landscape with a lake and dense forests.

West Stockbridge Hotel Guide - Hotels with Pool in West Stockbridge, Massachusetts

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Check availability on West Stockbridge Hotels with Pool

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
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 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.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
€146
includes taxes & fees
27 Sept - 28 Sept
The Yankee Inn
A backyard with a swimming pool, lounge chairs, and a hot tub.
A bar with wooden floors and shelves filled with bottles.
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.

2. 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
23 Sept - 24 Sept
The Red Lion Inn
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.
€129
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, seating area, and a bar.
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.
€110
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.
€126
includes taxes & fees
13 Sept - 14 Sept
Hampton Inn & Suites Berkshires-Lenox
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.
€110
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A large house with a balcony and a grassy yard.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A two-story building with a gabled roof and a chimney.

7. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
€108
includes taxes & fees
1 Sept - 2 Sept
The Little Lion
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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A bathroom with a white sink, mirror, and toilet.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
€76
includes taxes & fees
31 Aug - 1 Sept
Howard Johnson by Wyndham Lenox
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.

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.
€170
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Lenox Berkshires
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A hotel patio with outdoor seating and a fire pit.

10. 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.
€146
includes taxes & fees
27 Sept - 28 Sept
Hilton Garden Inn Lenox Pittsfield
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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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."
JAMES 2-night trip
Posted 21 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

10/10 Excellent
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Stacia 1-night trip
Posted 1 day ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great visit to Stockbridge. Can't think of a better place to stay than the iconic Red Lion Inn."
Daniel 2-night trip
Posted 2 days ago
The Red Lion Inn
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 7 days ago
Howard Johnson by Wyndham Lenox

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. Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: Features free self parking, an indoor pool and complimentary wireless Internet access. Vacation Village in the Berkshires: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Yankee Inn: 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 Ebenezer II Gifts and Antiques. Discover sights such as Charles H. Baldwin & Sons 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 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.