Find Hotels with a Pool in Chester, NY
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Our top choices for Chester hotels with a pool
Holiday Inn Express Hotel & Suites Chester by IHG
Holiday Inn Express Hotel & Suites Chester by IHGChester
8.6 out of 10, Excellent, (1009)
"The breakfast was a hit, the place is clean and I would stay here again."
elizabeth
$95 nightly
The price is $112
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
Erek
$215 nightly
The price is $243
Dec 29 - Dec 30
Total with taxes and fees
8.6 out of 10, Excellent, (1007)
"Room was clean and staff was great!"
Annemarie
$80 nightly
The price is $94
Jan 1 - Jan 2, 2026
Total with taxes and fees
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Holiday Inn Express Fishkill-Mid Hudson Valley by IHGFishkill
8.4 out of 10, Very Good, (1002)
"Very nice stay."
Peter
$95 nightly
The price is $107
Jan 9 - Jan 10, 2026
Total with taxes and fees
9.0 out of 10, Wonderful, (1008)
"Clean room, friendly staff, good breakfast"
Zuriber
$98 nightly
The price is $114
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
Ziwei
$294 nightly
The price is $346
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.6 out of 10, Excellent, (1002)
"It was a great place to stay "
Amanda
$92 nightly
The price is $104
Dec 29 - Dec 30
Total with taxes and fees
8.4 out of 10, Very Good, (1004)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
Ryan
$99 nightly
The price is $113
Jan 4 - Jan 5, 2026
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 Chester Hotel Reviews
Sleep Inn & Suites Middletown - Goshen
10/10 Excellent
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