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 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! (191 reviews)

"Great spot. Lots of history."

Reviewed on 12 Sept 2025

Brook Farm Inn

15 Hawthorne Street, Lenox, MA

2 min walk from Tanglewood Music Center

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! (127 reviews)

Perfect Berkshire Stay

"Everything was fabulous— the location, the common spaces, our room, the food and the staff. Beautiful grounds and close to everything"

Reviewed on 1 Sept 2025

Chambery Inn

199 Main St, Lee, MA

8 min drive from Tanglewood Music Center

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! (369 reviews)

"ease of late check in. Super comfortable room."

Reviewed on 24 Aug 2025

See all 1,108 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.