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

Find Hotels with a Pool in Stockbridge, MA

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Check availability on Stockbridge Hotels with a Pool

Tonight
Aug 27 - Aug 28
Tomorrow
Aug 28 - Aug 29
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Stockbridge hotels with a pool

A backyard with a swimming pool, lounge chairs, and a hot tub.
A covered porch with wicker furniture and hanging flower baskets.
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.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
NT$5,013
NT$7,180 total
includes taxes & fees
Sep 8 - Sep 9
The Red Lion Inn
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A two-story house with a brick entrance and a white facade.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

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.
NT$10,466
NT$12,661 total
includes taxes & fees
Sep 28 - Sep 29
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A backyard with a swimming pool, surrounded by grass and trees.
A modern bathroom with a black marble shower, gold fixtures, and a tiled floor.
A stone fountain surrounded by trees in a park setting.

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.
NT$11,997
NT$14,071 total
includes taxes & fees
Sep 14 - Sep 15
The Inn at Stockbridge
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.
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.

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.
NT$3,709
NT$4,762 total
includes taxes & fees
Sep 8 - Sep 9
Holiday Inn Club Vacations Oak 'n Spruce Resort
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.

5. 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.
NT$3,660
NT$4,088 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 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.
NT$4,818
NT$5,382 total
includes taxes & fees
Sep 27 - Sep 28
The Yankee Inn
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 sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

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.
NT$3,566
NT$3,983 total
includes taxes & fees
Sep 24 - Sep 25
The Little Lion
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 room with two beds, a desk, a television, and a dresser.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

8. 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.
NT$5,092
NT$5,688 total
includes taxes & fees
Sep 8 - Sep 9
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

9. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
NT$3,010
NT$4,074 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
A spacious hotel lobby with multiple seating areas, large windows, and a television.

10. 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.
NT$4,252
NT$4,750 total
includes taxes & fees
Sep 10 - Sep 11
Hampton Inn & Suites Berkshires-Lenox
View all properties

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 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 2 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Plenty of activities for couples and families to do…"
Ej 1-night trip
Posted 2 hours ago
Vacation Village in the Berkshires
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 7 hours 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 22 hours ago
The Red Lion Inn
The Inn at Stockbridge

The Inn at Stockbridge

10/10 Excellent
"The property and grounds are beautiful and perfectly appointed. The staff are friendly and accommodating. The room was very comfortable. The gym is small but was very functional for our purposes and we appreciated having it available. The pool is beautiful but sadly we were unable to use it as it was closed the afternoon we came back early to swim and enjoy the sun. Breakfast was outstanding all 3 days and we appreciated having an access to machine for espresso and cappuccino. Would definitely stay here again."
Connie 3-night trip
Posted 2 days ago
The Inn at Stockbridge
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 6 days ago
Howard Johnson by Wyndham Lenox
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
"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."
Lisa 1-night trip
Posted 6 days ago
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Frequently asked questions

What are some accommodations 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 sun loungers. 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 like Naumkeag Museum and Berkshire Botanical Garden. During your stay, check out 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 into account the local weather in 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 Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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