The Best Hotels with a Pool in Pittsfield, PA from ￥14,079 in 2026

Q: What are some hotels with pools in Pittsfield?

Charming Farmhouse on a working farm. : Resort steps from Peek'n Peak Ski Resort. Provides a seasonal outdoor pool, an indoor pool, and 6 restaurants. Peek'n Peak Resort Trademark Collection by Wyndham : Offers daily, an indoor pool, and free self parking. Clarion Pointe Jamestown - Falconer : Hotel, 1-minute walk from Chautauqua Lake. Features a seasonal outdoor pool, an indoor pool, and 2 bars. La Quinta Inn & Suites by Wyndham Jamestown : Offers a snack bar/deli, an indoor pool, and free self parking. Chautauqua Harbor Hotel - Jamestown : Provides a sauna, an indoor pool, and daily.

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Our top choices for Pittsfield hotels with a pool

Days Inn by Wyndham Warren

Warren

Splash into relaxation at this countryside retreat with year-round indoor pool and sauna service.

￥14,079 total

includes taxes & fees

Jul 12 - Jul 13

Peek'n Peak Resort Trademark Collection by Wyndham

Clymer

Mountain resort with dual pools, waterslide, and spa services makes for a blissful alpine splash retreat.

￥20,597 total

includes taxes & fees

Jul 20 - Jul 21

La Quinta Inn & Suites by Wyndham Jamestown

Jamestown

Lakeside retreat with year-round indoor pool for aquatic bliss in Chautauqua Lake's finest hotel.

￥22,101 total

includes taxes & fees

Jul 19 - Jul 20

Holiday Inn Express & Suites Jamestown by IHG

Jamestown

Refreshing swims await in the hotel's serene indoor pool, offering a splash of relaxation during any season.

￥30,422 total

includes taxes & fees

Jul 19 - Jul 20

Indoor pool, seasonal outdoor pool, sun loungers

Chautauqua Harbor Hotel - Jamestown

Celoron

Lakefront splashes and indoor dips await at this harbor hotel with year-round aquatic options.

￥41,904 total

includes taxes & fees

Jul 19 - Jul 20

DoubleTree by Hilton Jamestown

Jamestown

Splash into pure relaxation with the serene indoor pool sanctuary at this elegant lakeside retreat.

￥28,403 total

includes taxes & fees

Jul 22 - Jul 23

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

4 stars

Top Pittsfield Hotel Reviews

Peek'n Peak Resort Trademark Collection by Wyndham

10/10 Excellent

"We visited for an overnight in July. The grounds were well maintained. The room was clean and comfortable. The pool/fitness complex was clean and well-staffed. The Woods and Wedges breakfast wrap was a hit. I don't recommend the avocado toast. The service there was friendly and attentive."

Frequently asked questions

What are some hotels with pools in Pittsfield?

Charming Farmhouse on a working farm.: Resort steps from Peek'n Peak Ski Resort. Provides a seasonal outdoor pool, an indoor pool, and 6 restaurants. Peek'n Peak Resort Trademark Collection by Wyndham: Offers daily, an indoor pool, and free self parking. Clarion Pointe Jamestown - Falconer: Hotel, 1-minute walk from Chautauqua Lake. Features a seasonal outdoor pool, an indoor pool, and 2 bars. La Quinta Inn & Suites by Wyndham Jamestown: Offers a snack bar/deli, an indoor pool, and free self parking. Chautauqua Harbor Hotel - Jamestown: Provides a sauna, an indoor pool, and daily.

What is there to see and do in Pittsfield?

Make a point to visit attractions like Warren County Historical Society and Reg Lenna Center for The Arts. Discover sights such as Anders Run Natural Area and Cornplanter State Forest during your stay.

When is the best time to book a hotel with a pool in Pittsfield?

Taking into account the local weather in Pittsfield is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Pittsfield are January, November, March, and December, with each month seeing an average of 8 inches of snowfall.

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