Hotels with Swimming Pool in Pittsfield, Massachusetts

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Check availability on Pittsfield Hotels with Swimming 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, (1,005 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is P5,963
P6,661 total
includes taxes & fees
Mar 7 - Mar 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (836 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is P5,769
P7,751 total
includes taxes & fees
Feb 11 - Feb 12
Berkshire Mountain Lodge
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (666 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is P8,031
P8,970 total
includes taxes & fees
Feb 27 - Feb 28
Hilton Garden Inn Lenox Pittsfield
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (842 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 P5,027
P5,615 total
includes taxes & fees
Feb 18 - Feb 19
Berkshire Inn
Indoor pool

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, (82 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 P7,720
P8,623 total
includes taxes & fees
Mar 8 - Mar 9
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is P8,126
P9,077 total
includes taxes & fees
Feb 22 - Feb 23
Element Lenox Berkshires
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, (731 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is P6,256
P6,987 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (1,012 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is P5,417
P6,050 total
includes taxes & fees
Feb 22 - Feb 23
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, (833 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is P6,577
P8,490 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (830 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is P4,034
P4,506 total
includes taxes & fees
Feb 11 - Feb 12
Howard Johnson by Wyndham Lenox
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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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub

Top Pittsfield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Traveling during freezing temperatures was a challenge but once we arrived at the Yankee Inn, we felt welcome and comfortable. Pre check-in was easy and our room was clean and warm and cozy. We ordered in and were told there were tables on the 2nd floor outside the breakfast room where we could eat our dinner. All the staff were friendly and helpful. An easy choice whenever we return to the area."
AMY 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

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. Hotel On North: Offers buffet, an indoor pool, and complimentary wired internet access. Best Western Plus Berkshire Hills Inn & Suites: Features a snack bar/deli, a pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield - Berkshires by IHG: Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access.
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.

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