Find Romantic Hotels in Windsor, MA from $84
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Our top choices for Windsor romantic hotels
9.2 out of 10, Wonderful, (1000)
"Great stay there!! Very friendly staff"
Ann
$75 nightly
The price is $84
Dec 24 - Dec 25
Total with taxes and fees
$149 nightly
The price is $157
Dec 13 - Dec 14
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, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank
$93 nightly
The price is $104
Dec 14 - Dec 15
Total with taxes and fees
8.8 out of 10, Excellent, (1001)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
Joyce
$179 nightly
The price is $200
Jan 12 - Jan 13, 2026
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!Lanesborough
9.8 out of 10, Exceptional, (269)
"The cottage was amazing. Hope to be visit again and again. "
Mark M.
$187 nightly
The price is $209
Dec 13 - Dec 14
Total with taxes and fees
9.0 out of 10, Wonderful, (813)
"Easiest check in and out. Great food in dining room. "
William
$113 nightly
The price is $126
Dec 14 - Dec 15
Total with taxes and fees
9.4 out of 10, Exceptional, (53)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
alton
$200 nightly
The price is $212
Jan 7 - Jan 8, 2026
Total with taxes and fees
9.6 out of 10, Exceptional, (549)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
Jon
$186 nightly
The price is $208
Dec 14 - Dec 15
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 Red Lion Inn
10/10 Excellent
Frequently asked questions
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