Find Hotels with a Pool in Stockbridge, MA

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Check availability on Stockbridge Hotels with a 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, (1,010 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is AED 541
AED 768 total
includes taxes & fees
19 May - 20 May
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 AED 1,137
AED 1,375 total
includes taxes & fees
26 May - 27 May
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, (1,006 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is AED 364
AED 406 total
includes taxes & fees
19 May - 20 May
The Yankee Inn

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (931 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is AED 322
AED 442 total
includes taxes & fees
27 May - 28 May
Berkshire Mountain Lodge

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is AED 349
AED 390 total
includes taxes & fees
11 Jun - 12 Jun
The Little Lion

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,355 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is AED 317
AED 394 total
includes taxes & fees
17 May - 18 May
Vacation Village in the Berkshires

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (96 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is AED 414
AED 454 total
includes taxes & fees
13 May - 14 May
The Springs Motel

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,009 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is AED 503
AED 562 total
includes taxes & fees
17 May - 18 May
Hampton Inn & Suites Berkshires-Lenox

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 AED 613
AED 685 total
includes taxes & fees
19 May - 20 May
Element Lenox Berkshires

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (177 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is AED 543
AED 625 total
includes taxes & fees
13 May - 14 May
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.

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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.