Find Hotels with a Pool in Pittsfield, MA from CA $129

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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
Host meetings and events in style with a spacious conference room featuring large windows, polished floors, and elegant artwork.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (854)
"Consistently a clean room with welcoming staff."
The price is CA $158
CA $177 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Inn
Relax in comfort with a large bed and stylish seating area.

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (793)
"good location....easy access to highlight destinations and downtown"
The price is CA $129
CA $145 total
includes taxes & fees
Aug 24 - Aug 25
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield
Relax by the pool surrounded by lounge chairs and sunbeds, with views of the surrounding area and greenery.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (638)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is CA $204
CA $228 total
includes taxes & fees
Sep 7 - Sep 8
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.

Top Pittsfield Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"Great location!"
Natalie 2-night trip
Posted 23 hours ago
Hotel Downstreet, Ascend Hotel Collection

Frequently asked questions

What's it like visiting Pittsfield?
If relaxing 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 relax and unwind poolside at one of the accommodations in Pittsfield that guests like for their pools.
What are some accommodations with pools in Pittsfield?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. FairBridge Inn Express: Provides a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Best Western Plus Berkshire Hills Inn & Suites: Offers buffet, an indoor pool, and complimentary wired internet access. Berkshire Inn: Provides a snack bar/deli, a pool, and complimentary wired internet access.
How many pool hotels can I expect to find in Pittsfield?
Expedia has 7 hotels in Pittsfield for your poolside break.
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.