Hotels with Swimming Pool in Stockbridge, Massachusetts

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Check availability on Stockbridge Hotels with Swimming Pool

Tonight
Sep 21 - Sep 22
Tomorrow
Sep 22 - Sep 23
Next weekend
Sep 26 - Sep 28
In two weeks
Oct 3 - Oct 5

Top Stockbridge Hotels with Swimming Pool

Our top choices for Stockbridge hotels with a pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (40)
"Hotel was clean, the rooms had good space, the breakfast was excellent and the team there was very friendly and accommodating "
The price is P7,235
P8,081 total
includes taxes & fees
Sep 24 - Sep 25
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (59)
"Nice rooms"
Little Cat Lodge
The Springs Motel
Seasonal outdoor pool

The Springs Motel

2.0 star property
9.2 out of 10, Wonderful, (66)
"Chris was great!"
The price is P5,853
P6,421 total
includes taxes & fees
Sep 22 - Sep 23
The Springs Motel
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1007)
"great place have stayed several times, and hope to return."
The price is P10,225
P13,974 total
includes taxes & fees
Sep 28 - Sep 29
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)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is P17,678
P21,386 total
includes taxes & fees
Oct 6 - Oct 7
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Blackberry River Inn
Seasonal outdoor pool

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (135)
"Vintage antique home. Close to road, but was quiet at night."
The price is P9,388
P10,797 total
includes taxes & fees
Sep 22 - Sep 23
Blackberry River Inn
Hampton Inn & Suites Berkshires-Lenox
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1005)
"We enjoyed the quietness of the hotel and breakfast. It is very conveniantly located on RTR7/US20 but tucked off the road so its quiet "
The price is P7,720
P8,624 total
includes taxes & fees
Sep 28 - Sep 29
Hampton Inn & Suites Berkshires-Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Meeting facility

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (880)
"Our stay was very pleasant "
The price is P6,227
P6,955 total
includes taxes & fees
Sep 24 - Sep 25
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Yankee, Trademark Collection by Wyndham
Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1007)
"Nice area to visit "
The price is P6,264
P6,997 total
includes taxes & fees
Oct 1 - Oct 2
The Yankee, Trademark Collection by Wyndham
Huttopia Berkshires
Outdoor pool

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is P5,598
P6,253 total
includes taxes & fees
Sep 22 - Sep 23
Huttopia 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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Absolutely beautiful "
joanne 2-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

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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 2 indoor pools, 2 outdoor pools, and a snack bar/deli.
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.