Hotels with Swimming Pool in Pittsfield, Massachusetts

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Check availability on Pittsfield Hotels with Swimming Pool

Tonight
Jul 21 - Jul 22
Tomorrow
Jul 22 - Jul 23
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Top Pittsfield Hotels with Swimming Pool

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, (825)
"Very convenient location, downtown, short drive to local attractions "
The price is P7,378
P8,241 total
includes taxes & fees
Jul 27 - Jul 28
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (783)
"It was a good place to sleep for a quick visit to Pittsfield. Glad we booked there. "
The price is P5,490
P6,132 total
includes taxes & fees
Jul 22 - Jul 23
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 P10,967
P12,251 total
includes taxes & fees
Jul 27 - Jul 28
Hilton Garden Inn Lenox Pittsfield
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.