Find Hotels with a Pool in Pittsfield, MA

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Save instantly and earn perks with One Key

Learn about One Key

Change your mind

Book hotels with free cancellation

Check availability on Pittsfield Hotels with a Pool

Pick from 3 Pittsfield Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

"Nice & quiet property. Will love the food at the restaurant, JAE. "

AED 680 total

includes taxes & fees

28 May - 29 May

"loved how close to downtown the property is, we walked whwre we could. parking garage is closed for renovations but the staff was great and provided free valet and parked our car close or in front of the doors most days to help with us having a small child and my husband using a cane. loved the bar and pool as well. the hallways smelled strongly of weed but thankfully the smell stayed in the halls "

AED 398 total

includes taxes & fees

30 May - 31 May

"I liked how quiet it was. I liked the town"

AED 369 total

includes taxes & fees

27 May - 28 May

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.

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?

Surround yourself with nature at Pittsfield State Forest and Housatonic River. During your stay, check out sights such as Berkshire Museum, Colonial Theater, and Barrington Stage Company. 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.