The Berkshires Romantic Vacations
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Top Romantic The Berkshires Hotels
Shaker Mill Inn
2 Oak Street West Stockbridge MA
- 25 min walk from Tanglewood Music Center
Stay at this B&B in West Stockbridge. Enjoy free parking and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II Gifts and Antiques ...
9.6/10 Exceptional! (471 reviews)
"Cute and clean. Did not meet staff"
Reviewed on Aug 29, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
- 35 min drive from Tanglewood Music Center
A garden and in-room fireplaces await at this romantic aparthotel, which also offers a terrace and an outdoor pool.
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
- 16 min drive from Tanglewood Music Center
A garden and onsite dining await at this romantic hotel, which also offers a terrace and a bar.
7.8/10 Good! (1,003 reviews)
Couples like: onsite spa services, bar, winery tours
Travelers say...
"Nice place, would stay again"
Reviewed on Sep 15, 2026
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.
