Lenox Vacations from $378

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Your Lenox Vacation

There's loads to like about Lenox, from its cultural experiences to its spectacular views. When you're ready to say hi to this interesting city, our Lenox vacation packages are calling your name. Make your trip to Lenox even more fun by going sightseeing. Tanglewood Music Center, National Shrine of the Divine Mercy and Lee Premium Outlets are some of the major attractions you'll want to explore. No matter your travel plans or budget, organizing a tailored Lenox vacation is a walk in the park with Expedia.

The Latest Lenox vacation packages

Price found within the past 48 hours. Click for updated prices.
The Landing Hotel at Rivers Casino & Resort
Prospect Berkshires
The Equinox Golf Resort & Spa
Wilburton Inn
The Palmer House Resort, an Ascend Collection Hotel
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Discover the most popular places to visit in Lenox

Lenox Hotel Deals

Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $101 total per night from Jan 22 to Jan 23
$101 total
Jan 22 - Jan 23
Total with taxes and fees
9/10 Wonderful! (837 reviews)
Great food, nice room, nice staff.

Reviewed on Jan 14, 2026

Berkshires Untold
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Jan 29 to Jan 30
$103 total
Jan 29 - Jan 30
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
Best, kindest, most capable and courteous staff I’ve encountered in a long while.

Reviewed on Jan 20, 2026

The Yankee, Trademark Collection by Wyndham
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $155 total per night from Jan 26 to Jan 27
$155 total
Jan 26 - Jan 27
Total with taxes and fees
9.2/10 Wonderful! (596 reviews)
Large clean room and bathroom

Reviewed on Jan 12, 2026

Courtyard by Marriott Lenox 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.

Find the Best Lenox Vacation Packages

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1°C)Light RainMostly CloudyModerately LowAverage
February24.6°F (-4.1°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnyModerately HighAverage
July70.3°F (21.3°C)Light RainMostly SunnyModerately HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnyModerately HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyAverageAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnyModerately LowSlightly Low
December29.5°F (-1.4°C)Light RainMostly CloudyModerately LowAverage

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.

Lenox Essential Information

Language
English
Currency
U.S dollars
Population
1,700
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Norman Rockwell Museum, Ski Butternut and Bousquet Ski Area

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Frequently asked questions

How much does a Lenox vacation package cost?
You can pick up a vacation package to this destination from $378 on Expedia. But how much your vacation to Lenox costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Lenox?
You can typically find reduced prices and better availability in October, November and December. Check out our cheap Lenox vacation packages and you could land some great off-season discounts.
How many days is enough for Lenox?
You can easily see all the main attractions in Lenox in a few days, including the popular The Mount. If you're after a longer Lenox vacation, look at which kind of activities and excursions are available nearby.
Is it worth booking a vacation package to Lenox?
Lenox is a good vacation destination with attractions like Tanglewood Music Center among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Lenox vacation promises a good time for everyone.
How to find the best Lenox package deals?
Use Expedia's filters to find some fabulous Lenox package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Lenox package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Lenox vacation as a package?
You can enjoy significant savings on your Lenox getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Lenox?
If you're planning an impromptu Lenox getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Lenox?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Lenox.
  2. Set your budget: Consider expenses like flights, transportation and food when calculating how much to save for your trip to Lenox. Then, select a property that matches your budget, whether that's an affordable stay or a more upscale retreat.
  3. Use Expedia's trip planning tool to explore Lenox: Research every part of your trip to Lenox with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide your trip length: Think about how long you'd like to spend exploring Lenox. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  5. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, lock in the perfect Lenox vacation package for you.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to do and see. Browse some of the exciting things to do in Lenox and book your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Lenox vacation packages?
Set off on your perfect trip to Lenox with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains before they sell out.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.