Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

Top Pittsfield Hotels with a Pool

Holiday Inn Express & Suites Pittsfield - Berkshires
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is ₩209,535
₩234,051 total
includes taxes & fees
Jul 17 - Jul 18
Holiday Inn Express & Suites Pittsfield - Berkshires
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, (821)
"Very convenient location, downtown, short drive to local attractions "
The price is ₩158,373
₩176,902 total
includes taxes & fees
Jul 30 - Jul 31
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (513)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
The price is ₩122,911
₩168,057 total
includes taxes & fees
Jul 15 - Jul 16
Berkshire Mountain Lodge
Berkshire Inn
Relax in comfort with a large bed and stylish seating area.

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (779)
"The motel was nicely done and clean. The beds were comfortable "
The price is ₩137,702
₩153,815 total
includes taxes & fees
Jul 20 - Jul 21
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 ₩296,447
₩331,138 total
includes taxes & fees
Jul 27 - Jul 28
Hilton Garden Inn Lenox Pittsfield
Berkshire Travel Lodge
Enjoy a refreshing swim in our pool, surrounded by lush greenery and a serene landscape.

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (424)
"No hot water. Limited TV, coffee was burnt tar, musty smell, hideous very dark green wall. Yikes!"
The price is ₩96,663
₩104,403 total
includes taxes & fees
Jul 15 - Jul 16
Berkshire Travel Lodge
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, (1001)
"Fantastic place"
The price is ₩197,829
₩220,975 total
includes taxes & fees
Aug 13 - Aug 14
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Traditional buildings with welcoming front porches and easy street access.

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (395)
"Beautiful and peaceful property. Perfect for our last minute mother daughter get away. The staff was friendly and helpful. "
The price is ₩308,622
₩375,496 total
includes taxes & fees
Aug 4 - Aug 5
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, (390)
"No frills but it was a great stay!"
The price is ₩151,488
₩169,212 total
includes taxes & fees
Jul 21 - Jul 22
Sunset Inn
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
The price is ₩531,721
₩593,941 total
includes taxes & fees
Jul 16 - Jul 17
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.

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?
Best Western Plus Berkshire Hills Inn & Suites: Offers a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: 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 Herman Melville's Arrowhead. 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.