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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 2025/9/12

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 2025/9/1

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 2025/8/24

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.