Find Hotels with a Pool in Windsor, MA
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Our top choices for Windsor 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 & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (986)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank
$93 nightly
The price is $104
Dec 16 - Dec 17
Total with taxes and fees
8.8 out of 10, Excellent, (1004)
"Great property, nice staff, lovely rooms, awesome location."
Krysten
$124 nightly
The price is $139
Jan 8 - Jan 9, 2026
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
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
Edward
$103 nightly
The price is $115
Dec 14 - Dec 15
Total with taxes and fees
9.2 out of 10, Wonderful, (884)
"Clean, Great Staff, Quiet"
john
$79 nightly
The price is $88
Dec 14 - Dec 15
Total with taxes and fees
9.0 out of 10, Wonderful, (788)
"This place is so peaceful and the staff is always helpful "
Leona
$108 nightly
The price is $120
Jan 11 - Jan 12, 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 Windsor Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
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