Find Hotels with a Pool in Pittsfield, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with a Pool

Our top choices for Pittsfield hotels with a pool

Indoor pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,006 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is ₩144,414
₩161,311 total
includes taxes & fees
Jan 23 - Jan 24
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (663 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ₩188,445
₩210,493 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Lenox Pittsfield
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (816 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is ₩145,423
₩195,358 total
includes taxes & fees
Feb 1 - Feb 2
Berkshire Mountain Lodge
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (74 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is ₩187,714
₩209,676 total
includes taxes & fees
Jan 29 - Jan 30
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ₩126,716
₩141,541 total
includes taxes & fees
Jan 27 - Jan 28
Berkshire Inn
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (723 reviews)
"Always love staying here. The staff is fantastic, amenities are great, and the breakfast is just lovely. Will be returning soon!"
United States
Domenic
The price is ₩126,730
₩141,557 total
includes taxes & fees
Jan 22 - Jan 23
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ₩204,832
₩228,797 total
includes taxes & fees
Jan 26 - Jan 27
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The hotel is very nice and clean. From the moment we checked in to check out, we had an amazing time. "
United States
Gina
The price is ₩136,530
₩152,503 total
includes taxes & fees
Jan 27 - Jan 28
The Yankee, Trademark Collection by Wyndham
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (824 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is ₩165,781
₩213,986 total
includes taxes & fees
Jan 22 - Jan 23
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool, open 6:00 AM to 10 PM, sun loungers

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was pleasant and helpful, room spacey and all immaculate ."
United States
Barbara
The price is ₩185,134
₩206,794 total
includes taxes & fees
Feb 10 - Feb 11
Hotel Downstreet, an Ascend Collection Hotel
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.
View all properties

Top Pittsfield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Best, kindest, most capable and courteous staff I’ve encountered in a long while. "
Matthew 1-night trip
Posted 9 hours ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

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. Best Western Plus Berkshire Hills Inn & Suites: Offers buffet, an indoor pool, and complimentary wired internet access. Hotel On North: Features a snack bar/deli, a pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield - Berkshires by IHG: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children's pool, an indoor pool, and free self parking.
What is there to see and do in Pittsfield?
Surround yourself with nature at Housatonic River 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.