Find Hotels with a Pool in Pittsfield, PA

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Our top choices for Pittsfield hotels with a pool

Exterior
Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown
3.5 star property
Celoron
9.6 out of 10, Exceptional, (1001)
"Beautiful room, wonderful staff, excellent food and service. "
United States
Robert
$101 nightly
The price is $114
Jan 1 - Jan 2, 2026
Total with taxes and fees
Chautauqua Harbor Hotel - Jamestown
Indoor pool, sun loungers
DoubleTree by Hilton Jamestown

DoubleTree by Hilton Jamestown

DoubleTree by Hilton Jamestown
4.0 star property
Jamestown
8.8 out of 10, Excellent, (919)
"Clean, comfortable, and nice staff."
United States
Julie
$98 nightly
The price is $110
Jan 2 - Jan 3, 2026
Total with taxes and fees
DoubleTree by Hilton Jamestown
Indoor pool, outdoor pool, sun loungers
Peek'n Peak Resort Trademark Collection by Wyndham

Peek'n Peak Resort Trademark Collection by Wyndham

Peek'n Peak Resort Trademark Collection by Wyndham
3.5 star property
Clymer
8.6 out of 10, Excellent, (1000)
"Loved everything about this resort!! Highly reccomend to families! "
Canada
jennifer
$136 nightly
The price is $154
Dec 16 - Dec 17
Total with taxes and fees
Peek'n Peak Resort Trademark Collection by Wyndham
Indoor pool
La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown
3.0 star property
Jamestown
8.4 out of 10, Very Good, (1003)
"Nice hotel"
United States
Mason
$79 nightly
The price is $89
Jan 1 - Jan 2, 2026
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Jamestown
Indoor pool
Days Inn by Wyndham Warren

Days Inn by Wyndham Warren

Days Inn by Wyndham Warren
3.0 star property
Warren
6.8 out of 10, (1000)
"Nice place for the price. Bar was great and so was the food!"
United States
Dawn
$66 nightly
The price is $73
Dec 21 - Dec 22
Total with taxes and fees
Days Inn by Wyndham Warren
Indoor pool
Holiday Inn Express & Suites Jamestown by IHG

Holiday Inn Express & Suites Jamestown by IHG

Holiday Inn Express & Suites Jamestown by IHG
2.5 star property
Jamestown
9.2 out of 10, Wonderful, (791)
"Was great stay and the bfast was excellent "
United States
Deborah
$101 nightly
The price is $114
Jan 5 - Jan 6, 2026
Total with taxes and fees
Holiday Inn Express & Suites Jamestown by IHG
Exterior
Heron View Room at Carousel Bed and Breakfast

Heron View Room at Carousel Bed and Breakfast

Heron View Room at Carousel Bed and Breakfast
Russell
9.8 out of 10, Exceptional, (36)
"Beautiful comfortable stay- just lovely!"
United States
Leslie B.
$104 nightly
The price is $114
Jan 1 - Jan 2, 2026
Total with taxes and fees
Heron View Room at Carousel Bed and Breakfast
Pool
Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
Warren
$321 nightly
The price is $355
Jan 12 - Jan 13, 2026
Total with taxes and fees
Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
Smart TV, fireplace, video games, DVD player
Winterberry Lodge: Ski In/Out of this slopeside single condo. Best location!

Winterberry Lodge: Ski In/Out of this slopeside single condo. Best location!

Winterberry Lodge: Ski In/Out of this slopeside single condo. Best location!
Clymer
10.0 out of 10, Exceptional, (76)
"This was a great place for a summer vacation. Our extended family rented 3 houses and we could easily walk between them. Streetlights made it easy. There were plenty of activities to satisfy different age groups."
United States
Laurel B.
$1,314 nightly
The price is $1,485
Jan 4 - Jan 5, 2026
Total with taxes and fees
Winterberry Lodge: Ski In/Out of this slopeside single condo. Best location!
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

La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

10/10 Excellent
"Nice hotel"
Mason 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Jamestown

Frequently asked questions

What are some hotels with pools in Pittsfield?
Charming Farmhouse on a working farm.: Provides daily, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Jamestown: Resort steps from Peek'n Peak Ski Resort. Features a seasonal outdoor pool, an indoor pool, and 6 restaurants. Peek'n Peak Resort Trademark Collection by Wyndham: Provides a seasonal outdoor pool, an indoor pool, and 2 bars. Clarion Pointe Jamestown - Falconer: Features a snack bar/deli, an indoor pool, and free self parking. Cobblestone Inn & Suites - Corry: Offers a sauna, an indoor pool, and daily.
What is there to see and do in Pittsfield?
The picturesque setting of Allegheny River and Ashville Bay showcase the area's natural beauty. Discover sights such as Cornplanter State Forest and Anders Run Natural Area 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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