Hotels with Swimming Pool in Stockbridge, Massachusetts

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Check availability on Stockbridge Hotels with Swimming Pool

Tonight
Apr 26 - Apr 27
Tomorrow
Apr 27 - Apr 28
Next weekend
May 1 - May 3
In two weeks
May 8 - May 10

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, (1,001 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is P8,308
P11,994 total
includes taxes & fees
Apr 30 - May 1
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 P18,795
P22,737 total
includes taxes & fees
May 10 - May 11
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Indoor pool, seasonal outdoor pool, 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.
The price is P6,280
P7,014 total
includes taxes & fees
May 11 - May 12
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (916 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is P5,261
P7,233 total
includes taxes & fees
May 26 - May 27
Berkshire Mountain Lodge
Outdoor pool

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
  • cleanliness
    Dive into luxury poolside moments with a seasonal outdoor swimming area, vibrant bar service, and picturesque garden setting.
The price is P10,582
P12,305 total
includes taxes & fees
Apr 28 - Apr 29
Brook Farm Inn
Outdoor spa tub

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,340 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is P5,238
P6,517 total
includes taxes & fees
Apr 29 - Apr 30
Vacation Village in the Berkshires
Indoor pool

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, (758 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is P6,741
P7,530 total
includes taxes & fees
May 4 - May 5
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (556 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is P6,681
P7,462 total
includes taxes & fees
Apr 28 - Apr 29
The Little Lion
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, (1,001 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is P7,640
P8,534 total
includes taxes & fees
May 17 - May 18
Hampton Inn & Suites Berkshires-Lenox
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (852 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is P4,798
P5,359 total
includes taxes & fees
Apr 28 - Apr 29
Howard Johnson by Wyndham Lenox
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"A+ for everything and the only annoying thing at times was the card used to enter the room."
Michaely 2-night trip
Posted 3 hours ago
Vacation Village in the Berkshires

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. Provides full, a seasonal outdoor pool, and free self parking. Vacation Village in the Berkshires: Offers a children's pool, an indoor pool, and free self parking. Berkshires Untold: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Hotel located near National Shrine of the Divine Mercy. Features 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.

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