The Berkshires Romantic Vacations
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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! (393 reviews)
Charming stay in the Berkshires
"Only regret is that we did not stay longer! The inn was lovely, and the surrounding gardens were beautiful. With little ground light, we were surrounded by the universe in a way the city doesn’t allow"
Reviewed on Aug 21, 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! (1,957 reviews)
"A rare, affordable place in the Berkshires! The scenery is stunning, and we loved the pools (both indoor and out) and fire pit. The staff was friendly, and our room was spacious but dated: the blinds were broken, the doors stuck, the walls were paper thin and our king-size mattress had clearly seen ..."
Reviewed on Aug 18, 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! (863 reviews)
Couples like: onsite spa services, bar, winery tours
Travelers say...
"It was fine , no complaints"
Reviewed on Aug 19, 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.