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
  • Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Hotels with a Pool

This weekend
Next weekend

Our top choices for Stockbridge hotels with a pool

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is NT$4,286
NT$6,216 total
includes taxes & fees
Apr 14 - Apr 15
The Red Lion Inn

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, (110 reviews)
  • cleanliness
    Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
The price is NT$9,891
NT$11,966 total
includes taxes & fees
Apr 18 - Apr 19
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is NT$4,571
NT$5,105 total
includes taxes & fees
Apr 8 - Apr 9
Element Lenox Berkshires

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, (754 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is NT$3,548
NT$3,963 total
includes taxes & fees
Apr 9 - Apr 10
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (892 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is NT$2,769
NT$3,807 total
includes taxes & fees
May 3 - May 4
Berkshire Mountain Lodge

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 NT$3,643
NT$4,069 total
includes taxes & fees
Apr 14 - Apr 15
Hampton Inn & Suites Berkshires-Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (842 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is NT$2,525
NT$2,820 total
includes taxes & fees
Apr 4 - Apr 5
Howard Johnson by Wyndham Lenox

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,321 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is NT$3,323
NT$4,063 total
includes taxes & fees
Apr 16 - Apr 17
Vacation Village in the Berkshires

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (673 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is NT$4,087
NT$4,566 total
includes taxes & fees
Apr 5 - Apr 6
Hilton Garden Inn Lenox Pittsfield

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (555 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is NT$3,516
NT$3,927 total
includes taxes & fees
Apr 5 - Apr 6
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.

Choose what matters most at hotels with a pool in Stockbridge

Top Stockbridge Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Stockbridge?
The Red Lion Inn: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Features 3 restaurants, an outdoor pool, and spa services. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: B&B located near National Shrine of the Divine Mercy. Offers full, a seasonal outdoor pool, and free self parking. Vacation Village in the Berkshires: Features a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Hotel located near National Shrine of the Divine Mercy. 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.

Explore a world of travel with Expedia