Stockbridge Hotel Guide - Hotels with Pool in Stockbridge, Massachusetts

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Hotels with Pool

Tonight
6 Aug - 7 Aug
Tomorrow
7 Aug - 8 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Stockbridge Hotels with Pool

The Inn at Stockbridge
Outdoor pool

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Loved our visit"
The price is €221
includes taxes & fees
27 Aug - 28 Aug
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is €410
includes taxes & fees
19 Aug - 20 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Consistently a clean room with welcoming staff."
John 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

What's it like visiting Stockbridge?
If taking it easy by the pool is your idea of the perfect getaway, you may want to explore historic Stockbridge, which offers 5 places to stay with pools. While you're visiting, you can explore sights such as Naumkeag and National Shrine of the Divine Mercy, and then relax and unwind poolside at one of the accommodation options in Stockbridge that guests like for their pools.
What are some accommodation options with pools in Stockbridge?
The Red Lion Inn: Features 3 restaurants, an outdoor pool and spa services. Tanglewood Suites: Provides full, a seasonal outdoor pool and free self parking. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Vacation Village in the Berkshires: Offers a health club, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli.
How many hotels with pools are there in Stockbridge?
Expedia has 5 hotels in Stockbridge for your poolside break.
What is there to see and do in Stockbridge?
Make a point to visit attractions such as Naumkeag Museum and Berkshire Botanical Garden. During your stay, visit sights such as National Shrine of the Divine Mercy, Norman Rockwell Museum and Housatonic River. 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 the local weather in Stockbridge into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.