The Best Hotels with a Pool in West Stockbridge, MA from ₩95,368 in 2025

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

Pleasant Valley Motel West Stockbridge : Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires : Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG : Offers a health club, an indoor pool, and complimentary wired internet access. Berkshires Untold : Provides free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG : Features 3 restaurants, an outdoor pool, and spa services.

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Top West Stockbridge Hotels with a Pool

Guests can dine al fresco in this charming outdoor seating area with comfortable chairs and tables.

"Clean and convenient. Great value."

₩104,619 total

includes taxes & fees

Jul 29 - Jul 30

Top West Stockbridge Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"This was the best stay ever we had in our hotel’s section so far, "

The Yankee, Trademark Collection by Wyndham

10/10 Excellent

" The friendliness and excellent service received from the staff. While we stayed at the Yankee, we expected a delivery from UPS and the staff at the registration ensured that we would be informed as soon as it arrived at the Yankee. There was a delay from UPS and it caused us some stress. The Yankee staff made sure we were kept informed of the delivery. Their concern was greatly appreciated. Thank you."

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Frequently asked questions

What are some accommodations with pools in West Stockbridge?

Pleasant Valley Motel West Stockbridge: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers a health club, an indoor pool, and complimentary wired internet access. Berkshires Untold: Provides free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features 3 restaurants, an outdoor pool, and spa services.

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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