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

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Check availability on Stockbridge Hotels with 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, (1,004 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is 4.161.857 ₫
5.932.228 ₫ total
includes taxes & fees
8 Nov - 9 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 9.423.727 ₫
11.052.561 ₫ 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 9.866.611 ₫
11.935.786 ₫ total
includes taxes & fees
11 Nov - 12 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, (1,000 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
The price is 3.231.833 ₫
4.115.013 ₫ total
includes taxes & fees
1 Nov - 2 Nov
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 3.711.054 ₫
4.145.249 ₫ 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, (683 reviews)
  • cleanliness
    Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness centre.
The price is 3.245.009 ₫
3.624.674 ₫ total
includes taxes & fees
15 Nov - 16 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 2.325.060 ₫
2.597.092 ₫ total
includes taxes & fees
12 Nov - 13 Nov
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.

8. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,010 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is 2.739.676 ₫
3.060.166 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A large house with a balcony and a grassy yard.

9. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (636 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is 2.673.819 ₫
2.986.655 ₫ total
includes taxes & fees
29 Oct - 30 Oct
The Little Lion
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

10. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (715 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is 3.067.403 ₫
3.426.145 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
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.
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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
"We stayed at the Yankee Inn for 1 night. We had no problems with check-in. Our room was clean but outdated except the bathroom which was very nice. Good water pressure in the shower and the bed was comfortable. Unfortunately, due to myself not feeling well, we did not use the hot tub, enjoy the fire pit or try breakfast all of which would have likely improved our stay. Maybe next time!"
Jeanne 1-night trip
Posted 6 hours ago
The Yankee Inn

Frequently asked questions

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.