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

Find Hotels with a Pool in Stockbridge, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Hotels with a Pool

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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.

1. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is AED 562
AED 810 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A backyard with a swimming pool, surrounded by grass and trees.

2. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
  • cleanliness
    Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
The price is AED 1,340
AED 1,571 total
includes taxes & fees
12 Nov - 13 Nov
The Inn at Stockbridge
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (120 reviews)
  • cleanliness
    Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
The price is AED 1,178
AED 1,425 total
includes taxes & fees
12 Nov - 13 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

4. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,007 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
The price is AED 430
AED 552 total
includes taxes & fees
29 Oct - 30 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (818 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
The price is AED 528
AED 589 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with clear blue water, surrounded by windows with a view of trees.

6. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (682 reviews)
  • cleanliness
    Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
The price is AED 461
AED 515 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (846 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is AED 331
AED 369 total
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A large, two-story house with a well-maintained lawn and a fence.

8. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
  • cleanliness
    Escape to an elegant countryside retreat with an inviting outdoor pool, premium spa services, and made-to-order gourmet breakfast.
The price is AED 1,355
AED 1,514 total
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

9. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is AED 355
AED 396 total
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A large house with a balcony and a grassy yard.

10. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (635 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is AED 380
AED 425 total
includes taxes & fees
28 Oct - 29 Oct
The Little Lion
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Stockbridge

Breakfast included
Hot tub

Top Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"I enjoyed this hotel, mostly. Our room had a lovely heat generating gas fireplace. And having a private outside balcony to sit on was wonderful. My only gripe was the poor quality of the included free breakfast, and coffee! We skipped it entirely on our last morning there. But it looked like many people enjoyed it."
Stuart 4-night trip
Posted 3 hours ago
The Yankee Inn

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: Provides 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 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.