The Berkshires Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
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Shaker Mill Inn
2 Oak Street West Stockbridge MA
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! (461 reviews)
"Really clean, comfortable, and quiet. The pastries and fruit they provided were delicious too !"
Reviewed on 9 Jun 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
8.8/10 Excellent! (2,396 reviews)
"I enjoy staying here . The front desk staff was very friendly . I like the hours of outdoor and indoor pool . My only complaints is the rooms are very very outdated and had to go to front desk every day because keys didnt work ."
Reviewed on 15 Jun 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,009 reviews)
Couples like: on-site spa services, bar, winery tours
Travellers say...
"Undergoing a major renovation"
Reviewed on 14 Jun 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.
