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

Property grounds

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 pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night."
United States
Judith Pauline
The price is SAR 535
SAR 765 total
includes taxes & fees
19 May - 20 May
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.
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is SAR 1,161
SAR 1,405 total
includes taxes & fees
31 May - 1 Jun
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, (1,001 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
"Helpful and friendly staff, clean room, great pool amd jaccuzzi."
United States
Zina
The price is SAR 409
SAR 457 total
includes taxes & fees
28 May - 29 May
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (932 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
"Spacious, clean, and the pool was warm and perfect for family swimming"
United States
Danielle
The price is SAR 329
SAR 452 total
includes taxes & fees
24 May - 25 May
Berkshire Mountain Lodge
Exterior

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.
"we loved using the pool at the beautiful Red Lion"
United States
Lisa
The price is SAR 356
SAR 398 total
includes taxes & fees
11 Jun - 12 Jun
The Little Lion
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (178 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
"Pool was perfect."
United States
Diane
The price is SAR 532
SAR 611 total
includes taxes & fees
26 May - 27 May
Blackberry River Inn
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (93 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
"Clean rooms, friendly staff, pool was very clean"
United States
Camille
The price is SAR 442
SAR 494 total
includes taxes & fees
19 May - 20 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Outdoor spa tub

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,356 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
"Spacious suite, comfortable bed and the view of the ski slopes from the large indoor pool was amazing."
United States
Ellen
The price is SAR 324
SAR 403 total
includes taxes & fees
17 May - 18 May
Vacation Village in the Berkshires
Indoor pool

Element by Marriott Lenox Berkshires

Element by Marriott 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 room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is SAR 597
SAR 666 total
includes taxes & fees
28 May - 29 May
Element by Marriott Lenox Berkshires
Seasonal outdoor pool

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 pool is well maintained and cleaned."
United States
Geraldine
The price is SAR 391
SAR 429 total
includes taxes & fees
18 May - 19 May
The Springs Motel
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

Monument Mountain Motel

Monument Mountain Motel

4/10 Poor
"If you enjoy black mold in the bathroom, dirty sheets featuring spiders, and an all around ghetto experience this is for you! Staff was kind at least, but definitely recommend finding other accommodations. "
Samia 2-night trip
Posted 5 hours ago
Monument Mountain Motel

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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.