Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

Compare Pittsfield Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (749)
"The check in process was easy, and the front desk clerks were friendly. The parking garage is still not complete so the cars are parked off property. Getting a spot to temporarily park for the check in process can be challenging. Valet is an option which we used and would recommend. The staff was able to get our car quickly when requested. We had a concern on our 2nd night with smelling smoke in which we contacted the desk. They said they would send someone up to investigate, However there was...
The price is SAR 413
SAR 461 total
includes taxes & fees
22 Mar - 23 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (764)
"The room was very clean "
The price is SAR 323
SAR 360 total
includes taxes & fees
12 Mar - 13 Mar
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield
Indoor pool

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (629)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is SAR 490
SAR 548 total
includes taxes & fees
16 Mar - 17 Mar
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.
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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. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. Hotel On North: Offers a snack bar/deli, a pool, and complimentary wired internet access. Best Western Plus Berkshire Hills Inn & Suites: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Hilton Garden Inn Lenox Pittsfield: Features a sauna, a pool, and complimentary wireless 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, Bousquet Ski Area, and Hancock Shaker Village. 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.