Landoll's Mohican Castle, Christmas lights.

Hotels with Swimming Pool in Stockbridge, Massachusetts

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Check availability on Stockbridge Hotels with Swimming Pool

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, (1,006 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is P9,434
P13,282 total
includes taxes & fees
Jun 22 - Jun 23
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, (111 reviews)
  • cleanliness
    Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
The price is P20,278
P24,531 total
includes taxes & fees
Jul 12 - Jul 13
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,012 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is P6,830
P7,629 total
includes taxes & fees
Jun 16 - Jun 17
The Yankee Inn

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (563 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is P5,405
P6,037 total
includes taxes & fees
Jun 14 - Jun 15
The Little Lion

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (102 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is P8,310
P9,282 total
includes taxes & fees
Jun 14 - Jun 15
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (973 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is P7,470
P9,717 total
includes taxes & fees
Jun 17 - Jun 18
Berkshire Mountain Lodge

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is P8,511
P9,507 total
includes taxes & fees
Jun 18 - Jun 19
Hampton Inn & Suites Berkshires-Lenox

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (186 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is P9,563
P10,997 total
includes taxes & fees
Jun 18 - Jun 19
Blackberry River Inn

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (864 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is P4,852
P5,420 total
includes taxes & fees
Jun 14 - Jun 15
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, (2,392 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is P6,845
P8,320 total
includes taxes & fees
Jun 15 - Jun 16
Vacation Village in the Berkshires
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: 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. Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Berkshires Untold: Offers 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.

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