Search Hotels with Pool in Pittsfield

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Check availability on Pittsfield Hotels with Pool

Tonight
5 May - 6 May
Tomorrow
6 May - 7 May
This weekend
8 May - 10 May
Next weekend
15 May - 17 May

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, (923 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 2.310.633 ₫
3.169.435 ₫ total
includes taxes & fees
24 May - 25 May
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
9.2 out of 10, Wonderful, (92 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 3.450.671 ₫
3.854.479 ₫ total
includes taxes & fees
12 May - 13 May
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, (675 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 3.337.987 ₫
3.728.531 ₫ total
includes taxes & fees
17 May - 18 May
Hilton Garden Inn Lenox Pittsfield
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (854 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 2.107.017 ₫
2.353.569 ₫ total
includes taxes & fees
26 May - 27 May
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.
"Pool area is beautiful."
United States
edith
The price is 3.108.238 ₫
3.472.007 ₫ total
includes taxes & fees
17 May - 18 May
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
"Helpful and friendly staff, clean room, great pool amd jaccuzzi."
United States
Zina
The price is 2.723.659 ₫
3.042.122 ₫ total
includes taxes & fees
11 May - 12 May
The Yankee Inn
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (601 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 2.871.169 ₫
3.207.017 ₫ total
includes taxes & fees
6 May - 7 May
Maple Terrace Motel
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
"we loved using the pool at the beautiful Red Lion"
United States
Lisa
The price is 2.897.510 ₫
3.236.518 ₫ total
includes taxes & fees
7 May - 8 May
The Little Lion
Outdoor spa tub

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,347 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 2.271.898 ₫
2.826.670 ₫ total
includes taxes & fees
10 May - 11 May
Vacation Village in the Berkshires
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
"Plenty of parking and nice pool."
United States
Dan
The price is 2.080.939 ₫
2.324.408 ₫ total
includes taxes & fees
6 May - 7 May
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.
View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub

Top Pittsfield Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Breakfast was very good, but two machines were out of order, the juice one and one other. Ice Machine on our floor was AWOL otherwise great room and not dirty as another reviewer commented. Desk clerk did need to speak louder."
Rudolph 1-night trip
Posted 17 hours ago
Comfort Inn & Suites East Greenbush - Albany

Frequently asked questions

What is there to see and do in Pittsfield?
Make a point to visit attractions such as Housatonic River and Berkshire Museum. During your stay, visit sights such as Colonial Theater, Barrington Stage Company and Bousquet Ski Area. The sporting events and theatre 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 the local weather in Pittsfield into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 very many public transport options, so consider a car rental to maximise your time.