Find Hotels with a Pool in Stockbridge, MA

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Check availability on Stockbridge Hotels with a Pool

Tonight
Nov 1 - Nov 2
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Nov 2 - Nov 3
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Nov 7 - Nov 9
In two weeks
Nov 14 - Nov 16

Top Stockbridge Hotels with a Pool

Outdoor pool, sun loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1026)
"Food was great!"
United States
Emily
The price is ₩213,012
₩301,810 total
includes taxes & fees
Nov 6 - Nov 7
The Red Lion Inn
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
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (109)
"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 ₩442,421
₩535,214 total
includes taxes & fees
Nov 16 - Nov 17
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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, (684)
"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 ₩152,968
₩170,865 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (935)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is ₩147,250
₩164,478 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1025)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is ₩153,111
₩171,024 total
includes taxes & fees
Nov 2 - Nov 3
The Yankee, Trademark Collection by Wyndham
Indoor pool
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (741)
"Great stay, perfect "
United States
Lawrence
Berkshire Mountain Lodge
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, (2116)
"Good location; reasonable price; very clean and quiet - would definitely return"
United States
Steven
The price is ₩131,264
₩162,320 total
includes taxes & fees
Nov 12 - Nov 13
Vacation Village in the Berkshires
Seasonal outdoor pool
The Springs Motel
The Springs Motel
2.0 star property
9.2 out of 10, Wonderful, (83)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is ₩146,485
₩160,695 total
includes taxes & fees
Nov 2 - Nov 3
The Springs Motel
Indoor pool
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
9.6 out of 10, Exceptional, (9)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
The price is ₩192,997
₩215,578 total
includes taxes & fees
Nov 9 - Nov 10
Element Lenox Berkshires
Indoor pool
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (747)
"We had a nice stay at the Fairfield Inn in Great Barrington. It’s conveniently located not far from downtown and just a short drive to Stockbridge. The front desk staff was welcoming, the room spacious and clean, and plenty of breakfast items to choose from. Definitely recommend!"
United States
Denise
The price is ₩204,434
₩228,352 total
includes taxes & fees
Nov 5 - Nov 6
Fairfield Inn & Suites by Marriott Great Barrington Lenox/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
"Clean room and very friendly staff. "
Michael 2-night trip
Posted 2 days ago
The Red Lion Inn

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Frequently asked questions

What are some accommodations 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 free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Features a health club, an indoor pool, and complimentary wired internet access.
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 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 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.