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 ...
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! (1,970 reviews)
"The staff at Vacation Village are simply amazing! Super nice and very helpful. Very clean, lots of amenities, and spacious rooms! Will definitely stay again!"
Reviewed on 2025/8/24
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! (867 reviews)
Couples like: onsite spa services, bar, winery tours
Very good hotel
"The front of the building needs painting. Not enough parking. Staff was very professional and friendly."
Reviewed on 2025/8/27
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.