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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 Wi-Fi, free parking and daily housekeeping. Our guests praise the breakfast in their reviews. Popular attractions ...

8.8/10 Excellent! (181 reviews)

"Our stay at The Dewey was fantastic! Everything was easy and efficient, and it was so close to both town and Tanglewood. The bed was comfortable, the water pressure in the 3rd floor shower was fantastic, and the room was well-appointed without being overly crowded. I also have to commend the owners ..."

Reviewed on 14 Jul 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 Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...

9.6/10 Exceptional! (121 reviews)

Relaxing overnight!

"Beautiful spot in Lenox near Tanglewood. Enjoyed the pool and the front porch. Slept in and had a great breakfast out on the deck!"

Reviewed on 8 Jul 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 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

See all 1,116 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.