Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

Our top choices for Pittsfield hotels with a pool

Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (956 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is ₩174,147
₩228,033 total
includes taxes & fees
May 31 - Jun 1
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, (99 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is ₩202,497
₩226,189 total
includes taxes & fees
May 31 - Jun 1
Holiday Inn Express & 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, (678 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is ₩215,473
₩240,683 total
includes taxes & fees
Jun 4 - Jun 5
Hilton Garden Inn Lenox Pittsfield
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (859 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is ₩128,983
₩144,073 total
includes taxes & fees
Jun 1 - Jun 2
Berkshire Inn
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, (1,001 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is ₩182,998
₩204,403 total
includes taxes & fees
Jun 7 - Jun 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is ₩179,998
₩201,058 total
includes taxes & fees
Jun 1 - Jun 2
The Yankee Inn
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (910 reviews)
  • cleanliness
    Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is ₩126,898
₩149,308 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Corner Motel
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (562 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is ₩142,498
₩159,170 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is ₩255,146
₩352,019 total
includes taxes & fees
Jun 22 - Jun 23
The Red Lion Inn
Outdoor spa tub

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,375 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is ₩178,395
₩215,722 total
includes taxes & fees
Jun 2 - Jun 3
Vacation Village in the Berkshires
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Everything was perfect!"
Mary 1-night trip
Posted 19 hours ago
Hampton Inn & Suites Berkshires-Lenox

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.