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

Our top choices for Stockbridge hotels with a pool

Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is ￥24,163
￥34,097 total
includes taxes & fees
May 28 - May 29
The Red Lion Inn
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

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, (111 reviews)
  • cleanliness
    Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
The price is ￥52,520
￥63,534 total
includes taxes & fees
Jun 3 - Jun 4
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is ￥19,088
￥21,321 total
includes taxes & fees
Jun 1 - Jun 2
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (942 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is ￥13,954
￥19,141 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is ￥15,112
￥16,879 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
Outdoor spa tub

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,361 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is ￥13,720
￥17,070 total
includes taxes & fees
May 25 - May 26
Vacation Village in the Berkshires
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is ￥20,202
￥22,566 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is ￥22,044
￥24,623 total
includes taxes & fees
Jun 3 - Jun 4
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (97 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is ￥16,056
￥17,613 total
includes taxes & fees
May 21 - May 22
The Springs Motel
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (180 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is ￥24,024
￥27,627 total
includes taxes & fees
May 24 - May 25
Blackberry River Inn
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The staff was especially nice and helpful. The breakfast was one of the best. The music played in the breakfast room was fantastic. The location was great and very close to everything in Great Barrington. Will definitely stay there again."
James 1-night trip
Posted 5 hours ago
Quality Inn Great Barrington

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. Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Features a children's pool, an indoor pool, and free self parking. Berkshires Untold: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli.
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.