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Check availability on Stockbridge Hotels with Pool

Top Stockbridge Hotels with Pool

Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1016)
"Picture perfect Inn"
United States
jeff
The price is ฿4,896
฿6,938 total
includes taxes & fees
5 Nov - 6 Nov
The Red Lion Inn
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
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (108)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is ฿10,081
฿12,195 total
includes taxes & fees
4 Nov - 5 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Indoor pool
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
9.4 out of 10, Exceptional, (6)
"New hotel very nice"
United States
joel
The price is ฿4,398
฿4,912 total
includes taxes & fees
6 Nov - 7 Nov
Element Lenox Berkshires
Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (678)
"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "
United States
Tina
The price is ฿3,352
฿3,744 total
includes taxes & fees
13 Nov - 14 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Seasonal outdoor pool
The Springs Motel
The Springs Motel
2.0 star property
9.2 out of 10, Wonderful, (82)
"The Springs Motel was a delight! Something away from the boring, staple type of hotel. The staff was so friendly and welcoming. The coffee and breakfast is a great touch! Can't wait to go back"
United States
Tricia
The price is ฿3,338
฿3,662 total
includes taxes & fees
23 Oct - 24 Oct
The Springs Motel
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (915)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is ฿3,355
฿3,748 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1001)
"Very clean, nice amenities , great location!!"
United States
Erin
The price is ฿3,654
฿4,082 total
includes taxes & fees
9 Nov - 10 Nov
Hampton Inn & Suites Berkshires-Lenox
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2092)
"Great place!"
United States
Nicole
The price is ฿2,988
฿3,695 total
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Exterior
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (814)
"We enjoyed our stay. It's basic but clean and comfortable."
United States
Kit Ping
The price is ฿2,573
฿2,874 total
includes taxes & fees
23 Oct - 24 Oct
Howard Johnson by Wyndham Lenox
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool loungers
Prospect Berkshires
Prospect Berkshires
3.0 star property
9.4 out of 10, Exceptional, (11)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ฿8,725
฿10,847 total
includes taxes & fees
9 Nov - 10 Nov
Prospect Berkshires
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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Top Stockbridge Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"In a very nice annex suite."
Julia 2-night trip
Posted 3 days ago
The Red Lion Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
Amy 2-night trip
Posted 2 weeks ago
Jiminy Peak Mountain Resort

Frequently asked questions

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. Offers a children's pool, an indoor pool and free self parking. Vacation Village in the Berkshires: Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Provides a health club, an indoor pool and complimentary high-speed (wired) Internet access.
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.