Find Hotels with a Pool in Stockbridge, MA

Check availability on Stockbridge Hotels with a Pool

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Tonight
Aug 5 - Aug 6
Tomorrow
Aug 6 - Aug 7
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Stockbridge Hotels with a Pool

Huttopia Berkshires
Relax by the serene pool surrounded by lush greenery and lounge chairs.

Huttopia Berkshires

1.0 star property
$90 nightly
The price is $101
Sep 3 - Sep 4
Total includes taxes and fees
Huttopia Berkshires
Berkshire Mountain Lodge
Relax by the rectangular pool surrounded by lounge chairs and lush greenery.

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (542)
"Excellent stay!"
$146 nightly
The price is $164
Aug 24 - Aug 25
Total includes taxes and fees
Berkshire Mountain Lodge
The Red Lion Inn
Relax by the serene pool surrounded by lounge chairs and umbrellas.

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Loved our visit"
$214 nightly
The price is $240
Aug 14 - Aug 15
Total includes taxes and fees
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Enjoy a serene garden retreat with a lawn, pool, and lush greenery.

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 "
$425 nightly
The price is $475
Aug 19 - Aug 20
Total includes taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Blackberry River Inn
Relax by the pool surrounded by lush greenery and comfortable lounge seating.

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (122)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
$164 nightly
The price is $189
Sep 2 - Sep 3
Total includes taxes and fees
Blackberry River Inn
Howard Johnson by Wyndham Lenox
Enjoy a refreshing swim in our pool surrounded by a serene landscape.

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (775)
"My stay was perfect. I can't wait to stay there again. "
$79 nightly
The price is $88
Sep 1 - Sep 2
Total includes taxes and fees
Howard Johnson by Wyndham Lenox
The Springs Motel
Relax by the pool surrounded by a lush lawn and lounge chairs.

The Springs Motel

2.0 star property
9.0 out of 10, Wonderful, (53)
"Love this renovated motel. They made it cute and trendy"
$109 nightly
The price is $120
Aug 10 - Aug 11
Total includes taxes and fees
The Springs Motel
Hampton Inn & Suites Berkshires-Lenox
Enjoy a refreshing swim in our pool, surrounded by a spacious area with a clear view.

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1004)
"The breakfast."
$144 nightly
The price is $160
Sep 1 - Sep 2
Total includes taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Host meetings and events in style with a spacious conference room featuring large windows, polished floors, and elegant artwork.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (847)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
$115 nightly
The price is $128
Sep 1 - Sep 2
Total includes taxes and fees
Holiday Inn & Suites Pittsfield-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.

Top Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Very friendly staff. Restaurant/bar on sight very convenient."
Eithne 5-night trip
Posted 18 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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. 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 a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli.
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 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.