A river surrounded by autumn-colored trees and a forested hill.

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Check availability on Stockbridge Hotels with Pool

Tonight
27 Sept - 28 Sept
Tomorrow
28 Sept - 29 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Stockbridge hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.
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.
Rp2.820.080
Rp4.039.451 total
includes taxes & fees
30 Sept - 1 Oct
The Red Lion Inn
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.

2. 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.
Rp7.841.156
Rp9.196.413 total
includes taxes & fees
28 Sept - 29 Sept
The Inn at Stockbridge
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A two-story house with a brick entrance and a white facade.

3. 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.
Rp9.246.362
Rp11.185.562 total
includes taxes & fees
12 Oct - 13 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 building with a porch and multiple windows, surrounded by purple flowers.
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.
Rp2.094.651
Rp2.689.729 total
includes taxes & fees
29 Sept - 30 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 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.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

5. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
Rp1.933.524
Rp2.159.818 total
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn
An indoor swimming pool with clear lane markings, a poolside area with lounge chairs, and large windows allowing natural light.
A modern hotel lobby with seating areas, tables, and a reception desk.
A modern bathroom with a large mirror, a sink, and a shower.
A breakfast area with a counter, coffee machine, and a display of pastries.

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.
Rp2.130.457
Rp2.379.667 total
includes taxes & fees
19 Oct - 20 Oct
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 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.
Rp1.852.960
Rp2.069.756 total
includes taxes & fees
18 Oct - 19 Oct
The Little Lion
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 garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
Rp1.425.067
Rp1.991.753 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
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 covered outdoor area with stone pillars and a view of a road and green hills.

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.
Rp2.531.663
Rp2.827.867 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

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.
Rp2.219.614
Rp2.479.309 total
includes taxes & fees
20 Oct - 21 Oct
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"It was a well appointed suite with kitchen, dining area, living room with a fireplace and the bedroom and a nice quiet corner of the property. I did sit out on the balcony and watch the sun go down and I had the best night sleep. I’ve had in a long time I would definitely go back. I didn’t use any of the amenities that they charge extra for, but because I was traveling, it was nice to just have a quiet night in."
Rachel Elion 1-night trip
Posted 5 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"If you want a perfect New England experience, this is the place. The hotel is amazing, it’s older so don’t think you’re going to walk into a modern place, but don’t let that deter you, the vibe is great! Will definitely stay here again."
Michelle 2-night trip
Posted 7 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"A clean, well maintained, close to everything, motel. Would highly recommend and will stay again next time we are in the area."
Joan 1-night trip
Posted 12 hours ago
Quality Inn Great Barrington
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 6 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. Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. Quality Inn Great Barrington: Provides a seasonal outdoor pool, an indoor pool and buffet.
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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