Lenox Vacations from $280

Tanglewood Music Center

Rating: 9.6/10 (457 reviews)

Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.

See properties

The Mount

Rating: 9.4/10 (174 reviews)

Edith Wharton designed this 42-room mansion herself, showcasing her architectural vision alongside literary legacy. Explore elegant interiors and Italianate gardens while attending seasonal author events.

See properties

Photo by Ed Gaffny

Wyndhurst Golf & Club

Rating: 8.4/10 (46 reviews)

This historic 1926 golf course challenges players with tree-lined fairways and contoured greens against Berkshire mountain backdrops. Enjoy Wayne Stiles' classic design, then unwind at the elegant manor house.

See properties

Shakespeare and Company

Rating: 9.2/10 (76 reviews)

Experience world-class Shakespeare performances in the scenic Berkshires at one of America's largest Shakespeare festivals. Summer evening shows offer magical theatrical moments under the stars.

See properties

Lenox Mountain

Rating: 10.0/10 (2 reviews)

Hike through verdant forests to Lenox Mountain's summit for panoramic views of the Berkshire valleys. Fall visitors are rewarded with a spectacular tapestry of autumn foliage colors.

See properties

Ventfort Hall Mansion and Gilded Age Museum

Rating: 9.2/10 (65 reviews)

Explore the opulent 1893 Jacobean Revival mansion built for J.P. Morgan's sister during the Gilded Age. Immerse yourself in restored period rooms while enjoying Victorian teas or performances in authentic splendor.

See properties

Kennedy Park

Rating: 9.2/10 (86 reviews)

Kennedy Park's hardwood forests and carriage roads offer exceptional hiking and mountain biking trails. Explore scenic vistas during fall foliage when the landscape transforms into a vibrant natural spectacle.

See properties

Lenox Library

Rating: 9.0/10 (45 reviews)

The Lenox Library occupies a stately Greek Revival building, once the Berkshire County Courthouse. Browse Colonial manuscripts and rare first editions while admiring the beautifully restored 19th-century architecture.

See properties

Find out more about Lenox

Things to do in and around Lenox

Lenox, Massachusetts, offers a delightful mix of entertainment, romance, and culture. Enjoy thrilling music concerts and captivating theater performances, or hit the slopes for some skiing. For relaxation, explore wellness retreats and perks, and don’t miss out on a shopping spree. During the summer, take advantage of the seasonal guide and discover nearby attractions that enhance your vacation experience in this charming town.

Shopping

In Lenox, visit The Bookstore for a cozy selection of reads and gifts. Guido's Marketplace, just 4 miles away, offers a vibrant atmosphere with local produce and specialty items. Also, check out the Berkshire Mountain Country Store, located 4 miles from Lenox, for unique souvenirs and local goods.

Recreation

Experience the enchanting atmosphere at Tanglewood Music Center with its vibrant concerts, indulge in the cultural richness at Shakespeare and Company for a romantic theater night, or enjoy a day of outdoor fun at Wyndhurst Golf & Club, perfect for sports enthusiasts and families alike.

Adventure

Experience thrilling skiing at Bousquet Ski Area, located 4 miles from Lenox, where the slopes are perfect for both beginners and experts. For a scenic hike, venture 12 miles to Housatonic River Walk, offering breathtaking outdoor views. Ski Butternut, also 12 miles away, promises more exhilarating ski adventures.

Nightlife

In Lenox, Massachusetts, experience a charming nightlife with cozy bars and live music venues. Check out the historic Lenox Town Hall for performances, or enjoy a drink at a local pub. The serene atmosphere and friendly locals create a delightful evening vibe in this picturesque town.

Find the best attractions in and around Lenox

Lenox, Massachusetts, is a charming destination perfect for entertainment, romance, and cultural experiences. Visitors can explore historic houses, scenic reserves, and serene lakes, appealing to those seeking outdoor adventures or family-friendly activities. Notable attractions include the Lenox Collection, Historic Downtown Lenox, and luxury wellness resorts, making this quaint town an ideal getaway for diverse travelers looking to immerse themselves in culture and nature.

• National Shrine of the Divine Mercy: Located 5 miles from Lenox, this serene shrine offers a peaceful retreat with beautiful gardens and inspiring architecture. Visitors can engage in prayer and reflection, surrounded by a tranquil atmosphere that fosters spiritual connection and cultural appreciation.
• The Mount: Situated within Lenox, The Mount is the former home of author Edith Wharton. This historic house showcases Wharton's literary legacy, featuring stunning gardens and architectural design that reflect her artistic vision and connection to the Berkshires.
• Norman Rockwell Museum: Also located 5 miles away, this museum celebrates the life and work of iconic American artist Norman Rockwell. With a vast collection of his illustrations, visitors gain insight into American culture and nostalgia, enhancing their appreciation for art and storytelling.

Best time to go to Lenox

The best time to visit Lenox is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly cloudy with light rain.

Tips to save on your trip to Lenox

• Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Lenox.
• Consider traveling during the off-peak season (typically March to April and November) for more affordable package holidays to Lenox.
• Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
• Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Frequently Asked Questions

What's included in a Lenox vacation package?

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.

How can I save money on a Lenox vacation package?

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.

What's the best vacation package for Lenox?

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.

Is Lenox better suited for a beach vacation or a cultural trip?

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.

Is Lenox a good choice for a family vacation package?

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.

Are there adult-only vacation packages in Lenox?

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.

Which Lenox vacation packages include a mountain view?

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.

What are the top things to do in Lenox?

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.

Do you need to rent a car in Lenox, or is public transport enough?

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.

Are Lenox vacation package hotels conveniently located?

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.

Can I change or cancel my Lenox vacation package if my plans change?

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.

Do One Key members get extra savings when booking Lenox vacation packages?

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.

Does Expedia offer Book Now, Pay Later Lenox vacation packages?

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.

How do I find last-minute vacation packages to Lenox?

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.

How does free cancellation work on Lenox vacation packages?

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.

Is it cheaper to book a Lenox vacation as a package or separately?

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.

Why should I book my Lenox vacation package with Expedia?

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.

See less