The Berkshires Honeymoon Holidays
Book a Honeymoon 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 £335 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
Packages with flights are ATOL protected
Top Honeymoon The Berkshires Hotels
The Dewey
7 Hubbard Street, Lenox, MA
Stay at this 3.5-star guesthouse in Lenox. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the breakfast in their reviews. Popular attractions ...
8.8/10 Excellent! (184 reviews)
"Old world charm building with high ceilings and period features. Comfortable bed with nice bedding. En suite bathroom could use some love. One lightbulb was out and the toiletries weren’t fully stocked. Some visible mildew. Overall, a pleasant experience for our overnight stay."
Reviewed on 30 Jul 2025
Brook Farm Inn
15 Hawthorne Street, Lenox, MA
Stay at this 3.5-star B&B in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.6/10 Exceptional! (122 reviews)
"Maureen and her lovely staff operate a first class B&B. Thoughtful amenities and conveniences, clean and comfortable. Amazing home cooked breakfast, both plentiful and delicious. Thank you"
Reviewed on 19 Jul 2025
Chambery Inn
199 Main St, Lee, MA
Stay at this 3-star B&B in Lee. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Tanglewood Music Center and Berkshire Mountain ...
9.4/10 Exceptional! (368 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 13 Jun 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.
More holidays you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.