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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, (1003)
"Old time charm and hot tub under the stars"
United States
Lori
The price is NT$4,707
NT$6,660 total
includes taxes & fees
Jan 14 - 2026/1/15
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)
"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 NT$11,985
NT$14,498 total
includes taxes & fees
Jan 14 - 2026/1/15
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, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is NT$4,236
NT$4,732 total
includes taxes & fees
Jan 6 - 2026/1/7
Element Lenox 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, (1000)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is NT$2,768
NT$3,092 total
includes taxes & fees
Jan 3 - 2026/1/4
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"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 NT$7,908
NT$9,885 total
includes taxes & fees
Jan 14 - 2026/1/15
Prospect 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, (714)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is NT$3,075
NT$3,435 total
includes taxes & fees
Jan 25 - 2026/1/26
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, (1004)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is NT$3,174
NT$3,546 total
includes taxes & fees
Jan 11 - 2026/1/12
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, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is NT$4,013
NT$4,483 total
includes taxes & fees
Jan 2 - 2026/1/3
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, (1001)
"Very comfortable beds! "
United States
Gerald
The price is NT$3,436
NT$3,838 total
includes taxes & fees
Jan 4 - 2026/1/5
Hampton Inn & Suites Berkshires-Lenox

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, (813)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is NT$3,785
NT$4,841 total
includes taxes & fees
Jan 14 - 2026/1/15
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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: Provides 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. The Yankee, Trademark Collection by Wyndham: Offers a seasonal outdoor pool, an indoor pool, and buffet. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features 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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