Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

Tonight
Aug 3 - Aug 4
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Aug 4 - Aug 5
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Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Top Pittsfield Hotels with a Pool

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, (538)
"Excellent stay!"
The price is NT$2,843
NT$3,846 total
includes taxes & fees
Sep 2 - Sep 3
Berkshire Mountain Lodge
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, (843)
"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. "
The price is NT$3,447
NT$3,850 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (7)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is NT$4,815
NT$5,379 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires
Berkshire Inn
Relax by the serene pool surrounded by lush greenery and a tranquil atmosphere.

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (789)
"It was a good place to sleep for a quick visit to Pittsfield. Glad we booked there. "
The price is NT$2,997
NT$3,348 total
includes taxes & fees
Aug 4 - Aug 5
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield
Relax by the pool surrounded by lounge chairs and sunbeds, with views of the surrounding area and greenery.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is NT$4,762
NT$5,319 total
includes taxes & fees
Sep 2 - Sep 3
Hilton Garden Inn Lenox Pittsfield
Hotel Downstreet, Ascend Hotel Collection
Enjoy a lively swim in our indoor pool, featuring a vibrant mural and easy access via a ladder.

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1003)
"Clean,friendly staff and great location."
The price is NT$4,306
NT$4,809 total
includes taxes & fees
Sep 1 - Sep 2
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Relax by the serene pool surrounded by lounge chairs and umbrellas.

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (404)
"Very comfortable room that worked great for our family. "
The price is NT$5,579
NT$6,902 total
includes taxes & fees
Sep 2 - Sep 3
The Porches Inn at Mass MoCA
Sunset Inn
Enjoy a refreshing swim in our pool surrounded by a tiled edge.

Sunset Inn

2.0 star property
7.6 out of 10, Good, (397)
"No frills but it was a great stay!"
The price is NT$3,297
NT$3,683 total
includes taxes & fees
Aug 18 - Aug 19
Sunset Inn
Devonfield Inn B&B
Enjoy a romantic meal for two on this serene patio, surrounded by lush greenery and a beautiful view.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
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 Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Excellent "
craig 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires

Frequently asked questions

What's it like visiting Pittsfield?
If relaxing by the pool is your idea of the perfect getaway, you may want to consider historic Pittsfield, which offers 7 places to stay with pools. During your trip, you can explore sights such as Jiminy Peak Mountain Resort and Norman Rockwell Museum, and then relax and unwind poolside at one of the accommodations in Pittsfield that guests like for their pools.
What are some accommodations with pools in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features a health club, an indoor pool, and complimentary wired internet access. Best Western Plus Berkshire Hills Inn & Suites: Features free self parking, an indoor pool, and complimentary wireless internet access. FairBridge Inn Express: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Offers a snack bar/deli, a pool, and complimentary wired internet access. Hotel On North: Features buffet, an indoor pool, and complimentary wired internet access.
How many pool hotels can I expect to find in Pittsfield?
Expedia has 7 hotels in Pittsfield for your poolside break.
What is there to see and do in Pittsfield?
Make a point to visit attractions like Housatonic River and Berkshire Museum. During your stay, check out sights such as Colonial Theater, Barrington Stage Company, and Bousquet Ski Area. The sporting events and theater scene 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 Pittsfield?
Taking into account the local weather in Pittsfield can help you maximize your time at the pool during your trip. 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 Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to travel around Pittsfield?
Knowing the transportation options in Pittsfield can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have many public transit options to choose from so consider a car rental to maximize your time.