Lenox Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Lenox
Berkshires Untold
"From the time we showed up and told that they had no reservation for us, when we paid in full for a king suite, until we left, this experience was frustrating and full of problems. All king suites were sold out, including the one we paid for! We were told we would receive a 50% credit back to our ..."
Reviewed on 1 Jun, 2026
The Yankee Inn
"Beautiful and well maintained and close to shipping and food"
Reviewed on 29 May, 2026
Hampton Inn & Suites Berkshires-Lenox
"Spacious room with large walk-in shower, big bright breakfast room. Very pleasant."
Reviewed on 1 Jun, 2026
Popular places to visit
Shakespeare and Company
You can make plans for a show at Shakespeare and Company during your trip to Lenox. While you're in the area, stroll along the lakeside.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
