A nighttime view of a residential area with houses adorned with holiday lights.

Hotels with Swimming Pools in Stockbridge

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Check availability on Stockbridge Hotels with Swimming Pools

Tonight
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Stockbridge hotels with a pool

A backyard with a swimming pool, lounge chairs, and a hot tub.
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.
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.
S$292
includes taxes & fees
14 Sept - 15 Sept
The Red Lion 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.

2. 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.
S$508
includes taxes & fees
7 Sept - 8 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A backyard with a swimming pool, surrounded by grass and trees.

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.
S$562
includes taxes & fees
15 Sept - 16 Sept
The Inn at Stockbridge
A large indoor swimming pool with clear water, surrounded by walls with informational posters and a reception area with a 'Welcome' sign.
A multi-story hotel with balconies, a pond with rocks, and a clear sky.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.

4. 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
3 Sept - 4 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
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 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.

5. 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
An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.
A buffet with labeled containers for omelets and other dishes.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A Holiday Inn Express & Suites building with a stone facade, a covered entrance, and a parking lot.

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.
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 hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A two-story building with a gabled roof and a chimney.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.

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.
S$160
includes taxes & fees
1 Sept - 2 Sept
The Little Lion
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.

8. 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.

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.
S$185
includes taxes & fees
20 Sept - 21 Sept
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.

10. 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.
S$276
includes taxes & fees
25 Aug - 26 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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Choose what matters most at hotels with a pool in Stockbridge

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top Stockbridge Hotel Reviews

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

10/10 Excellent
"Loved our stay. Breakfast was amazing."
Patrick 1-night trip
Posted 14 hours ago
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"."
Mark 3-night trip
Posted 16 hours 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 1 day ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"What a wonderful stay! It was an impromptu overnight to the Berkshires and I’m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Kelly 1-night trip
Posted 1 day ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"…."
Tiago 3-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

Frequently asked questions

What are some accommodation options with pools in Stockbridge?
The Red Lion Inn: Features 3 restaurants, an outdoor pool and spa services. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Offers full, a seasonal outdoor pool and free self parking. The Inn at Stockbridge: Provides spa services, a seasonal outdoor pool and cooked-to-order. Vacation Village in the Berkshires: Features a sauna, a pool and sunloungers. The Yankee Inn: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool and free self parking.
What is there to see and do in Stockbridge?
Make a point to visit attractions such as Naumkeag Museum and Berkshire Botanical Garden. During your stay, visit sights such as National Shrine of the Divine Mercy, Norman Rockwell Museum and Stockbridge Bowl. The bars and historic landmarks 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 Stockbridge?
Taking the local weather in Stockbridge into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. 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 Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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