Lenox Vacations from $304

A Lenox vacation package lets you combine round-trip flights, hotel stays, and rental cars. Most hotels here offer free breakfast, providing a convenient start to your day, and about half of the package hotels feature mountain views, perfect for this ski destination outside the city. A small share of hotels also provide airport shuttle service to and from nearby airports like Bradley International Airport (BDL).


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

When you bundle, you can save up to 30%*. To save money on a Lenox package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

For couples seeking a romantic Lenox vacation package, consider a stay at the 3.5-star Brook Farm Inn, rated 9.1 out of 10. This charming property offers an outdoor pool and a restaurant, with travelers frequently praising its beautiful location and exceptional breakfast.


If you're looking for a luxury Lenox vacation package, the 4-star 33 Main is an excellent choice, rated 9.1 out of 10. This hotel is praised by travelers for its clean accommodations, delicious breakfast, and great location, about 1 mile from Tanglewood Music Center.


Travelers seeking the best value vacation packages in Lenox might consider the Howard Johnson by Wyndham Lenox, which costs around $120 per night. This hotel features an outdoor pool and is often highlighted by travelers for its good value and helpful staff, about 4 miles from Tanglewood Music Center.


*Package availability and prices may change depending on dates and demand.

Lenox offers a rich cultural experience for your Lenox vacation, set amidst the scenic Berkshire Mountains. This ski destination outside the city is particularly known for its arts, history, and romantic appeal.


Visitors can immerse themselves in music at Tanglewood Music Center, the summer home of the Boston Symphony Orchestra, or explore the elegant former home of Edith Wharton at The Mount, about a 15-minute walk from central Lenox. The Norman Rockwell Museum, about 6 miles away, also provides a deep dive into American art.

Lenox is a good choice for family vacation packages, especially for those seeking outdoor activities and cultural experiences in a scenic setting. Known for its family-friendly attractions, this ski destination outside the city offers a range of options for all ages.


Families can enjoy winter sports at Jiminy Peak Mountain Resort, about 6 miles from central Lenox, or explore the slopes at Bousquet Ski Area, about 2 miles away. For outdoor adventures, Mount Greylock, about 16 miles from central Lenox, provides opportunities for hiking and enjoying panoramic views. Your Lenox vacation package can be customized to include these family-friendly activities.

Yes, your Lenox vacation package can include an adults-only hotel, with options such as:


Browse adults-only resorts in Lenox on Expedia to compare options.

Many Lenox vacation packages include hotels with mountain views, as about half of package hotels offer this amenity. For example, Brook Farm Inn, rated 9.1 out of 10 by travelers, and The Cornell Inn, Lenox & The Berkshires, rated 8.6 out of 10 by travelers, are both options that may offer mountain-view rooms when building a Lenox vacation package. Keep in mind that specific room views often depend on the room type and rate booked.

Lenox offers a variety of attractions for your Lenox vacation, from cultural landmarks to outdoor adventures:


Browse and book things to do in Lenox on Expedia.

For a Lenox vacation package, a rental car is highly recommended for exploring beyond the immediate downtown area. While the small downtown of Lenox is easily walkable, and Tanglewood Music Center is about 1 mile from the central crossroads, many of the area's attractions are spread out.


As a ski destination outside the city, having a car provides the flexibility to reach various ski resorts like Jiminy Peak Mountain Resort, about 6 miles away, or explore natural sites such as Mount Greylock, about 16 miles from central Lenox. This allows you to make the most of your Lenox vacation packages with flights and experience the full range of what the region offers.

Lenox vacation package hotels are conveniently located, with many properties offering easy access to the town center. As Lenox is a ski destination outside the city, hotels are often positioned to balance proximity to both town amenities and natural attractions.


For instance, Gateways Inn & Restaurant is about a 5-minute walk from central Lenox, while 33 Main is also about a 5-minute walk, putting you close to local shops and dining. For those who prefer a slightly more spread-out setting, Eastgate Inn B&B is about 1 mile from central Lenox. Your Lenox vacation package can be tailored to a hotel that suits your preferred level of town access.

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Lenox vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

To find last-minute vacation packages to Lenox, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Free cancellation on a Lenox vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Lenox getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.