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Find Hotels with a Pool in Stockbridge, MA

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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)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ¥22,327
¥31,949 total
includes taxes & fees
Jan 20 - Jan 21
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 ¥59,847
¥72,399 total
includes taxes & fees
Jan 22 - Jan 23
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (15 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ¥21,781
¥24,330 total
includes taxes & fees
Jan 22 - Jan 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, (716 reviews)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is ¥15,357
¥17,153 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18 reviews)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ¥32,599
¥41,670 total
includes taxes & fees
Jan 25 - Jan 26
Prospect Berkshires

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, (1,003 reviews)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is ¥15,357
¥17,154 total
includes taxes & fees
Jan 30 - Jan 31
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is ¥14,667
¥19,446 total
includes taxes & fees
Jan 15 - Jan 16
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires 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, (1,000 reviews)
"Everything was great! "
Canada
Daphne
The price is ¥15,850
¥17,705 total
includes taxes & fees
Jan 22 - Jan 23
The Yankee, Trademark Collection by Wyndham

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ¥20,039
¥22,383 total
includes taxes & fees
Jan 30 - Jan 31
Hilton Garden Inn Lenox Pittsfield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is ¥12,379
¥13,827 total
includes taxes & fees
Jan 10 - Jan 11
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.

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. Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers a health club, an indoor pool, and complimentary wired internet access. The Yankee, Trademark Collection by Wyndham: Features 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.