The Berkshires Honeymoon Holidays 2026

Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Honeymoon The Berkshires Hotels

The Dewey

7 Hubbard Street Lenox MA

13 min walk from Tanglewood Music Center

Stay at this guesthouse in Lenox. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the breakfast in their reviews. Popular attractions ...

8.6/10 Excellent! (330 reviews)

"There is no staff on site. Fire alarm went off no one showed up for 20 mins. The shower situation was less than desirable. The property outside was not weeded and lacked any care. Any guest that I spoke to all felt the same. We go once a year to Lenox and will not be staying there."

Reviewed on 7 July 2026

Brook Farm Inn

15 Hawthorne Street Lenox MA

2 min walk from Tanglewood Music Center

Stay at this B&B in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions Tanglewood ...

9.4/10 Exceptional! (173 reviews)

"This was a beautiful place to spend a relaxing vacation . The grounds are beautiful with flowers , plenty of places to sit and relax and a lovely pool area. The daily breakfast was delicious . Maureen and Bob were wonderful hosts and their staff very nice . I look forward to a return visit."

Reviewed on 25 Aug 2026

Chambery Inn

199 Main St Lee MA

8 min drive from Tanglewood Music Center

Stay at this B&B in Lee. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Tanglewood Music Center and Berkshire Mountain Country ...

9.6/10 Exceptional! (387 reviews)

"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."

Reviewed on 1 Sept 2026

See all 1,088 properties in The Berkshires

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.