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Hotels with Swimming Pools in Pittsfield

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Check availability on Pittsfield Hotels with Swimming Pools

Our top choices for Pittsfield hotels with a pool

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, (1,009 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is S$281
includes taxes & fees
22 Jul - 23 Jul
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,015 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is S$222
includes taxes & fees
20 Aug - 21 Aug
Berkshire Mountain Lodge
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, (1,004 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is S$187
includes taxes & fees
28 Jul - 29 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (887 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is S$130
includes taxes & fees
27 Jul - 28 Jul
Berkshire Inn
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (138 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is S$245
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-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, (885 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is S$143
includes taxes & fees
27 Jul - 28 Jul
Howard Johnson by Wyndham Lenox
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is S$283
includes taxes & fees
26 Jul - 27 Jul
Hampton Inn & Suites Berkshires-Lenox
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (697 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is S$293
includes taxes & fees
26 Jul - 27 Jul
Hilton Garden Inn Lenox Pittsfield
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,463 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is S$204
includes taxes & fees
26 Jul - 27 Jul
Vacation Village in the Berkshires
Indoor pool

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (28 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is S$342
includes taxes & fees
29 Jul - 30 Jul
Element by Marriott Lenox 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

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

8/10 Good
"Nice hotel, clean and quiet."
Kathleen 1-night trip
Posted less than an hour ago
Comfort Inn & Suites East Greenbush - Albany

Frequently asked questions

What are some accommodation options with pools in Pittsfield?
Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. FairBridge Inn Express: Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Features a health club, an indoor pool and free valet parking. Best Western Plus Berkshire Hills Inn & Suites: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Hotel On North: Features a snack bar/deli, a pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Pittsfield?
Surround yourself with nature at Housatonic River and Onota Lake. During your stay, visit sights such as Berkshire Museum, Colonial Theater 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.

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