Find Hotels with a Pool in Pittsfield, NY
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Our top choices for Pittsfield hotels with a pool
8.4 out of 10, Very Good, (1002)
"Very great place to stay"
Jase
$71 nightly
The price is $81
Dec 21 - Dec 22
Total with taxes and fees
9.4 out of 10, Exceptional, (837)
"The room was spotless, breakfast was great and the staff were fantastic. "
Kathleen
$99 nightly
The price is $113
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.4 out of 10, Very Good, (1003)
"Clean comfortable most awesome bed and bath. I needed a good night’s sleep and this really helped as I couldn’t travel home because of the horrible weather! "
Melissa
$90 nightly
The price is $103
Dec 18 - Dec 19
Total with taxes and fees
9.8 out of 10, Exceptional, (103)
"Excellent stay! Clean and close to downtown."
Carla
$106 nightly
The price is $121
Dec 21 - Dec 22
Total with taxes and fees
9.2 out of 10, Wonderful, (1003)
"The staff was really welcoming and kind. The hotel was very clean and I loved the decorations for the holidays. "
Philomena
$95 nightly
The price is $109
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2 out of 10, Wonderful, (709)
"Great stay!"
Lisa
$131 nightly
The price is $149
Dec 19 - Dec 20
Total with taxes and fees
9.6 out of 10, Exceptional, (237)
"Friendly staff and one of the best B&B we ever been. "
Shan
$160 nightly
The price is $182
Dec 14 - Dec 15
Total with taxes and fees
Vacation Like Gatsby on This Historic 500-Acre Fairy Tale Estate
Vacation Like Gatsby on This Historic 500-Acre Fairy Tale EstateGilbertsville
9.2 out of 10, Wonderful, (36)
"Beautiful location"
Anonymous traveler
$1,708 nightly
The price is $1,947
Dec 16 - Dec 17
Total with taxes and fees
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
Best Western Cooperstown Inn & Suites
10/10 Excellent
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