The Berkshires Honeymoon Vacations
Book a Honeymoon Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
Better together
Save up to ￥45,448 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 Honeymoon The Berkshires Hotels
The Dewey
7 Hubbard Street, Lenox, MA
Stay at this 3.5-star guesthouse in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast in our reviews. Popular attractions ...
8.8/10 Excellent! (180 reviews)
"excellent stay!! The Dewey is a cozy getaway location!"
Reviewed on Jun 29, 2025
Brook Farm Inn
15 Hawthorne Street, Lenox, MA
Stay at this 3.5-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (119 reviews)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you."
Reviewed on Dec 13, 2024
Chambery Inn
199 Main St, Lee, MA
Stay at this 3-star B&B in Lee. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Tanglewood Music Center and Berkshire Mountain ...
9.4/10 Exceptional! (366 reviews)
"Beautiful stay. We booked last minute and it was amazing! We were able to book the room with jacuzzi and a fireplace—which made the whole stay so romantic. Will recommend and am planning to visit regularly. Hoping to return in the fall but definitely next spring. This family works hard and takes ..."
Reviewed on Jun 13, 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.