The Berkshires Romantic Vacations
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Photo by Photo courtesy of Berkshire Visitors Bureau
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Top Romantic The Berkshires Hotels
Shaker Mill Inn
2 Oak Street, West Stockbridge, MA
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II ...
9.6/10 Exceptional! (392 reviews)
"Very casual and easy check in and out; lovely and substantial breakfast"
Reviewed on Aug 11, 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
A garden and in-room fireplaces await at this romantic condo, which also offers a terrace and an outdoor pool.
8.6/10 Excellent! (1,950 reviews)
Love Vacation Village!
"Love everything about this place. If you want a true home away from home this is the place. The only miss is streaming abilities for at night, but an extra hdmi to type C cable,and we were all set!"
Reviewed on Aug 16, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
A garden and onsite dining await at this romantic hotel, which also offers a terrace and a bar.
7.8/10 Good! (860 reviews)
Couples like: onsite spa services, bar, winery tours
Travelers say...
"This is my "go to" when I'm in Pittsfield. It's central, convenient, clean and comfortable."
Reviewed on Aug 17, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.