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 property in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer ...
9.6/10 Exceptional! (385 reviews)
"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"
Reviewed on 2025/7/2
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! (1,860 reviews)
"Activities look good during week but we miss them on our weekend stay"
Reviewed on 2025/7/8
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! (818 reviews)
Couples like: onsite spa services, bar, winery tours
Travelers say...
"Clean but needs renovations"
Reviewed on 2025/7/8
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.