The Best Hotels with a Pool in West Stockbridge, MA from ₩131,789 in 2026

Q: What are some accommodations with pools in West Stockbridge?

Shaker Mill Inn : Provides free self parking, an indoor pool, and complimentary wireless internet access. Pleasant Valley Motel West Stockbridge : Offers a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge : Features 3 restaurants, an outdoor pool, and spa services. Berkshires Untold : Offers a seasonal outdoor pool, an indoor pool, and buffet. Vacation Village in the Berkshires : Provides buffet, an indoor pool, and complimentary wired internet access.

Olivias Overlook - West Stockbridge, Massachusetts

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Our top choices for West Stockbridge hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

₩233,584 total

includes taxes & fees

Jun 24 - Jun 25

The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

₩350,493 total

includes taxes & fees

Jun 9 - Jun 10

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.

₩241,994 total

includes taxes & fees

Jun 22 - Jun 23

Berkshire Mountain Lodge

Pittsfield

Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.

₩258,172 total

includes taxes & fees

Jun 29 - Jun 30

Blackberry River Inn

Norfolk

Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.

₩267,415 total

includes taxes & fees

May 31 - Jun 1

The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

₩166,370 total

includes taxes & fees

Jun 1 - Jun 2

The Springs Motel

New Ashford

Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.

₩208,275 total

includes taxes & fees

Jun 2 - Jun 3

Howard Johnson by Wyndham Lenox

Lenox

Summertime splashes await at this refreshing outdoor pool oasis in Lenox.

₩131,789 total

includes taxes & fees

Jun 10 - Jun 11

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Choose what matters most at hotels with a pool in West Stockbridge

Breakfast included

4 stars

Top West Stockbridge Hotel Reviews

The Red Lion Inn

10/10 Excellent

"We love the laid back shabby chic comfort of the Inn. It is our third visit in 2 years and a delightful getaway. The food is excellent. Breakfast has a good choice of menu options . We also love the pool"

Vacation Village in the Berkshires

4/10 Poor

"So after answering all questions that could only lead to a “decent” review here’s what happened. Check in was fine, it was a check in; friendly and we checked in. We get to the room and I leave to grab food for our dinner, my wife calls front desk because of awful noises upstairs, people stomping around like they’re getting paid to. I get back and she’s still on the phone after desk telling her everything is fixed… okayyy but we still hear incredible stomping. Lady insisted everything is fixed it must be a kid…..right but our room sounds like an industrial zone. Do we have to beg to be moved to a new room when this place is mostly vacant? Our food is cold and we’re on the phone again noise won’t stop even though I’m listening on ALL FLOORS for the source of noise, finally agrees to move us to a top floor in a new building. We haul our stuff over, keycards maintenance brought us don’t work. He says he’ll get new ones (very nice guy btw). ONE of the two new cards works after he comes back and he tries for a few minutes to get it to slide in at the perfect angle and velocity. Finally we get to settle into our new room for the last few hours we would be awake. Thanks for a wonderful finale to our one anniversary night away from kiddos. At least there was a tub to relax in this room. This place would have been fine if it weren’t for the horrible sound enhancing construction and front desk person who tried their best not to solve an easy problem."

Frequently asked questions

What are some accommodations with pools in West Stockbridge?

Shaker Mill Inn: Provides free self parking, an indoor pool, and complimentary wireless internet access. Pleasant Valley Motel West Stockbridge: Offers a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge: Features 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Offers a seasonal outdoor pool, an indoor pool, and buffet. Vacation Village in the Berkshires: Provides buffet, an indoor pool, and complimentary wired internet access.

What is there to see and do in West Stockbridge?

Make a point to visit attractions like Stockbridge Bowl and Charles H. Baldwin & Sons. During your stay, check out sights such as Hoffman's Pottery, Hotchkiss Mobile Studio, and Ebenezer II Gifts and Antiques. The gardens and restaurants 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 West Stockbridge?

Taking into account the local weather in West 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 West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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