Find Hotels with a Pool in Pittsfield, MA

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Our top choices for Pittsfield hotels with a 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, (1,002 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is AED 360
AED 402 total
includes taxes & fees
30 Jan - 31 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 AED 503
AED 562 total
includes taxes & fees
30 Jan - 31 Jan
Hilton Garden Inn Lenox Pittsfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (819 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is AED 362
AED 487 total
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (79 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is AED 468
AED 522 total
includes taxes & fees
29 Jan - 30 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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 AED 313
AED 349 total
includes taxes & fees
27 Jan - 28 Jan
Berkshire Inn

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, (727 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is AED 367
AED 410 total
includes taxes & fees
29 Jan - 30 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (17 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is AED 511
AED 570 total
includes taxes & fees
1 Feb - 2 Feb
Element Lenox Berkshires

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,011 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is AED 340
AED 380 total
includes taxes & fees
2 Feb - 3 Feb
The Yankee, Trademark Collection by Wyndham

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (892 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is AED 274
AED 324 total
includes taxes & fees
27 Jan - 28 Jan
Cozy Corner Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (90 reviews)
"Great vibe. Comfortable great staff"
United States
Bart
The price is AED 439
AED 482 total
includes taxes & fees
27 Jan - 28 Jan
The Springs Motel
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.

Top Pittsfield Hotel Reviews

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Frequently asked questions

What are some accommodations with pools in Pittsfield?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers a health club, an indoor pool, and complimentary wired 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.