The Berkshires Romantic Vacations
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 togetherSave up to NT$5,067 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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! (446 reviews)
Spacious, clean, nice breakfast
Reviewed on 2026/2/15
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.
8/10 Very Good! (1,000 reviews)
Couples like: onsite spa services, bar, winery tours
Travelers say...
Staff was pleasant! Clean and the restaurant was excellent!
Reviewed on 2026/3/22
The Dewey
7 Hubbard Street Lenox MA
Romance awaits at this guest house, which features a garden and a lobby fireplace. Couples will appreciate the luxury bedding and terrace.
8.6/10 Excellent! (329 reviews)
If you decide one day to spend twice what a place is worth, this is for you.
Reviewed on 2025/10/21
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.
