Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

Top Pittsfield Hotels with a Pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (899)
"Excellent customer service and great rooms"
The price is ₩146,784
₩163,958 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (53)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is ₩169,871
₩189,737 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Berkshire Mountain Lodge
Indoor pool
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (701)
"Great stay, perfect "
The price is ₩132,822
₩180,199 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
Hilton Garden Inn Lenox Pittsfield
Indoor pool
Hilton Garden Inn Lenox Pittsfield
3.0 star property
9.2 out of 10, Wonderful, (651)
"Nice quiet hotel, easy in and out, friendly staff"
The price is ₩186,174
₩207,964 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Lenox Pittsfield
Berkshire Inn
Seasonal outdoor pool
Berkshire Inn
2.0 star property
7.8 out of 10, Good, (830)
"This property has a mid century motel look from the street but the rooms have been recently upgraded and are fully modern inside. A great value and comfortable place to stay"
The price is ₩113,993
₩127,332 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Inn
Element Lenox Berkshires
Indoor pool
Element Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
The price is ₩192,387
₩214,896 total
includes taxes & fees
Nov 9 - Nov 10
Element Lenox Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (675)
"Great place to have a girls night for old friends when one of us is back in town for a night. Very convenient place well kept. "
The price is ₩147,069
₩164,270 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Springs Motel
Seasonal outdoor pool
The Springs Motel
2.0 star property
9.2 out of 10, Wonderful, (77)
"The Springs Motel was a delight! Something away from the boring, staple type of hotel. The staff was so friendly and welcoming. The coffee and breakfast is a great touch! Can't wait to go back"
The price is ₩146,021
₩160,185 total
includes taxes & fees
Nov 2 - Nov 3
The Springs Motel
Howard Johnson by Wyndham Lenox
Exterior
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (809)
"Good for the one night drive through! "
The price is ₩112,582
₩125,750 total
includes taxes & fees
Oct 19 - Oct 20
Howard Johnson by Wyndham Lenox
Cozy Corner Motel
Exterior
Cozy Corner Motel
2.0 star property
9.2 out of 10, Wonderful, (873)
"Very nice staff, nice breakfast"
The price is ₩106,454
₩125,664 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Corner 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.
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Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Room was comfortable and clean. The Inn is beautiful. We went to the Lions Den both evenings and had a drink and listened to live music. We couldn’t get a table at the restaurant but there are other good options in walking distance. The only disappointment was that the fireplace in our room was not working. "
Beth 2-night trip
Posted 1 day ago
The Red Lion Inn

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. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers a health club, an indoor pool, and complimentary wired internet access. Best Western Plus Berkshire Hills Inn & Suites: Features buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield - Berkshires by IHG: 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 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 Colonial Theater, Barrington Stage Company, and Bousquet Ski Area. 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.