Hotels with Swimming Pool in Stockbridge, Massachusetts

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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, (1,001 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is P8,807
P12,460 total
includes taxes & fees
Mar 9 - Mar 10
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)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is P18,169
P21,980 total
includes taxes & fees
Feb 20 - Feb 21
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,001 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is P5,989
P6,689 total
includes taxes & fees
Mar 7 - Mar 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is P8,197
P9,156 total
includes taxes & fees
Feb 22 - Feb 23
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, (731 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is P6,282
P7,017 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is P5,760
P6,434 total
includes taxes & fees
Feb 8 - Feb 9
The Yankee, Trademark Collection by Wyndham

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (832 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is P6,605
P8,526 total
includes taxes & fees
Feb 10 - Feb 11
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (665 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is P7,998
P8,933 total
includes taxes & fees
Mar 8 - Mar 9
Hilton Garden Inn Lenox Pittsfield

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"The room and amenities were amazing. "
United States
Kathleen
The price is P6,998
P7,817 total
includes taxes & fees
Mar 1 - Mar 2
Hampton Inn & Suites Berkshires-Lenox

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
United States
Pablo
The price is P6,458
P7,214 total
includes taxes & fees
Feb 9 - Feb 10
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: Features 3 restaurants, an outdoor pool, and spa services. Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshires Untold: Offers a health club, an indoor pool, and complimentary wired internet access.
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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