Hotels with Swimming Pool, Stockbridge Massachusetts

Q: 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.

Linwood House at the Norman Rockwell Museum Stockbridge Massachusetts USA.

Significant collection of the artist's original work & memorabilia on display in his hometown.

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Our top choices for Stockbridge hotels with a pool

The Red Lion Inn

Stockbridge

Gary

P12,460 total

includes taxes & fees

Mar 9 - Mar 10

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

Stockbridge

Deborah

P21,980 total

includes taxes & fees

Feb 20 - Feb 21

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Steven

P6,689 total

includes taxes & fees

Mar 7 - Mar 8

Element Lenox Berkshires

Lenox

Mary

P9,156 total

includes taxes & fees

Feb 22 - Feb 23

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Shanice

P7,017 total

includes taxes & fees

Feb 22 - Feb 23

Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

Lenox

Giselle

P6,434 total

includes taxes & fees

Feb 8 - Feb 9

2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

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

South Lee

Thomas

P8,526 total

includes taxes & fees

Feb 10 - Feb 11

Hilton Garden Inn Lenox Pittsfield

Pittsfield

MARY

P8,933 total

includes taxes & fees

Mar 8 - Mar 9

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Choose what matters most at hotels with a pool in Stockbridge

Breakfast included

Hot tub

Top Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"The staff is super friendly and accommodating. The location is quiet. We stayed during the winter, but the lake view from the restaurant and breakfast area were really nice. The hotel was well kept and clean. We’ll definitely stay there again. "

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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