Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

Our top choices for Pittsfield hotels with a pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (943 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
"Spacious, clean, and the pool was warm and perfect for family swimming"
United States
Danielle
The price is NT$2,777
NT$3,809 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
"Clean rooms, friendly staff, pool was very clean"
United States
Camille
The price is NT$4,020
NT$4,491 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & 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, (678 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
"One night. Clean room. Kids enjoyed the hot tub and pool even though it’s not very large. Convenient location. "
United States
Meaghan
The price is NT$4,009
NT$4,478 total
includes taxes & fees
May 28 - May 29
Hilton Garden Inn Lenox Pittsfield

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (856 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
"This is a very convenient motel -- it is easy to get to, has a nice pool, quiet area, comfortable room,"
United States
Donald W
The price is NT$2,532
NT$2,829 total
includes taxes & fees
May 26 - May 27
Berkshire Inn

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, (1,000 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
"Pool area is beautiful."
United States
edith
The price is NT$3,862
NT$4,314 total
includes taxes & fees
May 28 - May 29
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
"Pool and hot tub are terrific, great breakfast spread, convenient location, super comfortable mattress."
United States
Emma
The price is NT$3,799
NT$4,243 total
includes taxes & fees
Jun 2 - Jun 3
The Yankee 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, (765 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
"The pool was very clean."
United States
Alessandro
The price is NT$3,925
NT$4,385 total
includes taxes & fees
Jun 1 - Jun 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (906 reviews)
  • cleanliness
    Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
"The views from the property were beautiful. Parking was easy. The bathroom was lovely. "
United Kingdom
NICOLA
The price is NT$2,507
NT$2,955 total
includes taxes & fees
May 31 - Jun 1
Cozy Corner Motel

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,361 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
"Spacious suite, comfortable bed and the view of the ski slopes from the large indoor pool was amazing."
United States
Ellen
The price is NT$2,730
NT$3,397 total
includes taxes & fees
May 25 - May 26
Vacation Village in the Berkshires

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (606 reviews)
  • cleanliness
    Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
"Great stay in good location, if you can use the pool while the horses are out it is very nice"
United States
Kenneth
The price is NT$3,451
NT$3,854 total
includes taxes & fees
May 31 - Jun 1
Maple Terrace 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.

Choose what matters most at hotels with a pool in Pittsfield

Top Pittsfield Hotel Reviews

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. Hotel On North: Provides a health club, an indoor pool, and free valet parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers buffet, an indoor pool, and complimentary wired internet access. Best Western Plus Berkshire Hills Inn & Suites: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Holiday Inn Express & Suites Pittsfield - Berkshires by IHG: Provides a snack bar/deli, a pool, and complimentary wired internet access.
What is there to see and do in Pittsfield?
Make a point to visit attractions like Housatonic River and Berkshire Museum. During your stay, check out sights such as Barrington Stage Company, Bousquet Ski Area, and Hancock Shaker Village. 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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