Hotels with Swimming Pool in Stockbridge, Massachusetts

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Top Stockbridge Hotels with Swimming Pool

The Inn at Stockbridge
Outdoor pool

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1020)
"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. The dinner was delicious. Plenty of seats but gave us a table facing wall (but near window) —why not more in middle of room area with more interesting view! And same table for breakfast and...
The price is P8,849
P12,521 total
includes taxes & fees
Dec 1 - Dec 2
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, sun 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)
"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 P27,028
P32,696 total
includes taxes & fees
Nov 24 - Nov 25
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. Life House Berkshires: Features a seasonal outdoor pool, an indoor pool, and buffet. The Yankee, Trademark Collection by Wyndham: Offers 2 indoor pools, 2 outdoor pools, and 2 restaurants. The Black Swan Lee - Lenox, Ascend Hotel Collection: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children’s pool, an indoor pool, and a health club. Quality Inn: Features a health club, an indoor pool, and complimentary wired internet access.
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 Berkshire Theatre Festival. 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.