Photo by Elizabeth Massa Peroulakis
Find Hotels with a Pool in Chester, MA
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Our top choices for Chester hotels with a pool
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
joel
$131 nightly
The price is $146
Dec 22 - Dec 23
Total with taxes and fees
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
Linda
$75 nightly
The price is $84
Dec 24 - Dec 25
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHGPittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
Jeffrey
$113 nightly
The price is $126
Jan 11 - Jan 12, 2026
Total with taxes and fees
9.0 out of 10, Wonderful, (1002)
"Everything was perfect: clean room, great breakfast, courteous staff!"
Tiffany
$87 nightly
The price is $99
Dec 22 - Dec 23
Total with taxes and fees
9.4 out of 10, Exceptional, (2249)
"Stayed 3 nights, really great hotel and value. "
Vince
$121 nightly
The price is $135
Dec 15 - Dec 16
Total with taxes and fees
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
Pamela
$79 nightly
The price is $88
Dec 14 - Dec 15
Total with taxes and fees
8.4 out of 10, Very Good, (798)
"Love the staff"
Sherry
$84 nightly
The price is $96
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.4 out of 10, Very Good, (816)
"Very pet friendly and the night check in agent was super kind and friendly"
olivia townsend
$103 nightly
The price is $115
Jan 13 - Jan 14, 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
D. Hotel Suites & Spa
10/10 Excellent
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