Photo by William Keller

Hotels with Swimming Pools in Stockbridge

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Hotels with Swimming Pools

Next weekend
In two weeks

Top Hotels with Swimming Pools in Stockbridge

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is S$265
includes taxes & fees
15 Dec - 16 Dec
The Red Lion Inn

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

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"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 S$604
includes taxes & fees
7 Dec - 8 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very good, (962)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is S$130
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is S$191
includes taxes & fees
21 Dec - 22 Dec
Element Lenox Berkshires

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1006)
"Great stay!"
United States
Ann
The price is S$108
includes taxes & fees
14 Dec - 15 Dec
The Yankee, Trademark Collection by Wyndham

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (696)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is S$156
includes taxes & fees
25 Nov - 26 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2141)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is S$123
includes taxes & fees
23 Nov - 24 Nov
Vacation Village in the Berkshires

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (87)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is S$156
includes taxes & fees
23 Nov - 24 Nov
The Springs Motel

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (825)
"Staff was very friendly and helpful."
United States
Pamela
The price is S$115
includes taxes & fees
4 Dec - 5 Dec
Howard Johnson by Wyndham Lenox

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (788)
"Place was great!"
United States
Benjamin
The price is S$174
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.

Black Friday Sale

Save up to 50% on select hotels

Top Stockbridge Hotel Reviews

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. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Offers full, a seasonal outdoor pool and free self parking. Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features 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 Stockbridge Bowl. 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.