Find Hotels with a Pool in Stockbridge, MA

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Pick from 5 Stockbridge Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

The Inn at Stockbridge
Pool

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge
The Red Lion Inn
Outdoor pool

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"The feel of an old fashioned Christmas feel"
The price is SAR 774
SAR 1,032 total
includes taxes & fees
19 Dec - 20 Dec
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Outdoor pool

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is SAR 1,594
SAR 1,929 total
includes taxes & fees
1 Jan - 2 January 2025
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.
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Frequently asked questions

What's it like visiting Stockbridge?
If taking it easy by the pool is your idea of a great vacation, you may want to check out historic Stockbridge, which offers 5 places to stay with pools. During your trip, you can explore sights such as Naumkeag and National Shrine of the Divine Mercy, and then kick back and relax poolside at one of the accommodations in Stockbridge that guests like for their pools.
What are some accommodations with pools in Stockbridge?
The Red Lion Inn: Features 3 restaurants, an outdoor pool, and spa services. The Yankee, Trademark Collection by Wyndham: Provides a seasonal outdoor pool, an indoor pool, and buffet. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel: Offers a health club, an indoor pool, and complimentary wired internet access. The Black Swan Lee - Lenox, Ascend Hotel Collection: Offers 2 indoor pools, 2 outdoor pools, and 2 restaurants. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children’s pool, an indoor pool, and a health club.
How many hotels with pools will I find 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 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 Beartown State Forest. 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.