Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence

Better together

Save up to CA $1,096 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

Plan, book, and manage your trip all in one place

Honeymoon Hotels in The Berkshires

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! (186 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 Jul. 30, 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! (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 Jul. 19, 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! (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 Jun. 13, 2025

See all 1,107 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.