The Berkshires Romantic Holidays
Book a Romantic Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
- Plan, book, travel with confidence
Better together
Save up to ₹43,962 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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! (402 reviews)
Brief stay. Was decent. Didnt get to see much more than the room itself
Reviewed on 28 Oct 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,106 reviews)
Good location; reasonable price; very clean and quiet - would definitely return
Reviewed on 27 Oct 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (928 reviews)
Couples like: on-site spa services, bar, winery tours
Travellers say...
Everything is clean
Reviewed on 27 Oct 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.
