Pittsfield Hotel Guide - Hotels with Pool in Pittsfield, Massachusetts

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Top Pittsfield Hotels with Pool

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
8.0 out of 10, Very good, (682)
"We stayed for two weeks and couldn’t have been happier with the service. Such nice people, and so understanding. Six stars if I could!"
The price is €100
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn
2.0 star property
7.6 out of 10, Good, (747)
"Nice area "
The price is €91
includes taxes & fees
4 Dec - 5 Dec
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield
Indoor pool
Hilton Garden Inn Lenox Pittsfield
3.0 star property
9.2 out of 10, Wonderful, (618)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is €143
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Lenox Pittsfield
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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Frequently asked questions

What's it like visiting Pittsfield?
If laying by the pool is your idea of the perfect getaway, you may want to consider historic Pittsfield, which offers 7 places to stay with pools. During your trip, you can explore sights such as Jiminy Peak Mountain Resort and Norman Rockwell Museum, and then take it easy poolside at one of the accommodation options in Pittsfield that guests like for their pools.
What are some accommodation options with pools in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel: Features a health club, an indoor pool and complimentary high-speed (wired) Internet access. FairBridge Inn Express: Provides free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Hotel On North: Offers a snack bar/deli, a pool and complimentary high-speed (wired) Internet access. Best Western Plus Berkshire Hills Inn & Suites: Offers 3 restaurants, an outdoor pool and spa services.
How many pool hotels will I be able to find in Pittsfield?
Expedia has 7 hotels in Pittsfield for your poolside break.
What is there to see and do in Pittsfield?
Surround yourself with nature at Pittsfield State Forest and Housatonic River. 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.