Find Hotels with a Pool in Pittsfield, MA

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Pool

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very Good, (701)
"Staff was very accommodating. The pool area was quite nice and it was deep"
The price is AED 364
AED 406 total
includes taxes & fees
5 Jan - 6 January 2025
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (753)
"This is a nice motel, though there is no continental breakfast. There is a pot of coffee made at 7am. The rooms are clean and updated, the mattress is good, airconditioner in back wall, simple round thermostat for hot water radiator heating, mini-fridge is compressor type, microwave."
The price is AED 316
AED 353 total
includes taxes & fees
23 Dec - 24 Dec
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield
Pool

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (620)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is AED 536
AED 599 total
includes taxes & fees
31 Dec - 1 January 2025
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.
Don't see what you're looking for?
See all available properties in Pittsfield

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, an IHG Hotel: 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. Best Western Plus Berkshire Hills Inn & Suites: Features a snack bar/deli, a pool, and complimentary wired internet access. Hilton Garden Inn Lenox Pittsfield: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Berkshire Inn: Provides free self parking, an indoor 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?
Surround yourself with nature at Pittsfield State Forest and Canoe Meadows Wildlife Sanctuary. During your stay, check out sights such as Berkshire Museum, Colonial Theater, 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.