Lenox Vacations 2026 from CA $908

Lenox flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Hotel Vervana, Trademark Collection by Wyndham

CA $908

per person

Apr 17 - Apr 20

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this ski hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Museum are located nearby.

Top Lenox hotels deals

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $125

CA $140 total

Apr 5 - Apr 6

includes taxes & fees

Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $126

CA $140 total

Mar 15 - Mar 16

includes taxes & fees

Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $191

CA $214 total

Mar 12 - Mar 13

includes taxes & fees

Book a stay at this business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.

The Cornell Inn, Lenox & The Berkshires

203 Main St Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $181

CA $208 total

Mar 8 - Mar 9

includes taxes & fees

Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $151

CA $169 total

Mar 15 - Mar 16

includes taxes & fees

Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

The Ponds at Foxhollow

3 Foxhollow Drive Route 7 Lenox MA

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Stay at this condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.

Pool

Kitchen

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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.

Popular places to visit

A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

Tanglewood Music Center

5/5(6 reviews)

You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.

The Mount

You can spend an afternoon studying the exhibits at The Mount during your trip to Lenox. While you're in the area, stroll along the lakeside.

Great resort, right up the street from Tanglewood in the Berkshires. Gorgeous view looking west to New York

Wyndhurst Golf & Club

5/5(1 review)

Enjoy a round of golf in Lenox at Wyndhurst Golf & Club. While you're in the area, stroll along the lakeside.

Lenox Vacations

Even if you're the most impulsive adventurer, it still doesn't hurt to know a couple of things about Lenox before you go. Find it on the map, write down the activities on offer and let the good times roll!

Lenox lies 110 miles (177 kilometers) west of Boston, a significant city.

With plenty of things to do in this area of The Berkshires, it's easy to see why 2,000 people choose to call it home.

Hotels in Lenox

Every incredible journey starts with a single step — as well as a comfortable place to lay your weary head! Lock in your Lenox accommodations through Travelocity and you'll have 45 properties to select from.

Splurge on a touch of luxury at the Blantyre (16 Blantyre Rd) or the Hampton Terrace Inn (91 Walker Street). After all, it's not every day you take a vacation! The Gateways Inn & Restaurant (51 Walker St) and the Econo Lodge Lee - Great Barrington (980 Pleasant Street) are some thrifty options if you'd prefer to spend your cash on experiences.

Places to visit in Lenox

Theater challenges how we think and asks us to aspire to more. Attend a play at Shakespeare and Company and open your mind to some big ideas. Like some more options? Sure, having a dance to music on your stereo is fun, but it doesn't beat the excitement of seeing a breathtaking live performance! So why not splurge on tickets to a concert at Tanglewood Music Center? And that's not all. It's hard to see how people once functioned at home without all the modernized equipment we use today. Take a look around The Mount and discover how they did.

Where do you fly into for Lenox?

Get ready for some unforgettable new experiences! The heart of Lenox is approximately 45 miles (72 kilometers) northwest of Bradley International Airport (BDL).

Frequently asked questions

How much are vacation packages to Lenox?

Travelocity has package deals to Lenox, including hotels and flights, starting from as low as CA $908. With all that extra money, you could purchase some cool tours or perhaps even add some extra nights to your vacation.

How long should my Lenox vacation be?

Most sightseers vacation in Lenox for an average of 2 nights. That being said, traveling is all about checking out new things and creating memories — why not book a few more nights to do just that?

Where can I get the best vacation package deals for Lenox?

There are excellent Lenox package deals to be scored with Travelocity. Did you know we partner with 400 airlines and 1,000,000 worldwide properties? Remember this the next time you're ready to check another destination off your bucket list.

Why should I purchase my Lenox vacation package via Travelocity?

From incredible destinations to fun experiences, we have everything you need to satisfy your wanderlust. Our 24/7 support will also ensure you're being taken care of before, during and after your trip. And don't panic if you spot a cheaper price on your reservation, we'll match it. That's our Price Match Guarantee.

Can I save on my Lenox car rental if I book it with hotels and flights?

With a Lenox vacation package, you can bundle your flight, hotel and car bookings and save tons. If you're in the mood to explore the best of this fabulous area, why not make a beeline for Times Square? This well-known sight is 193 kilometers from Lenox. With your own wheels, you'll be there in no time.

Which airport is best for Lenox?

There's a good chance you'll touch down at Bradley Intl. Airport (BDL), which is 72 kilometers southeast of inner Lenox. Albany Intl. Airport (ALB) (64 kilometers away from central Lenox) and Hartford, CT (HFD-Hartford - Brainard) (88 kilometers away from central Lenox) are other choices.

What is there to do in Lenox?

You'll notice a certain kind of magic as you roam the streets of Lenox. The Mount and Ventfort Hall Mansion and Gilded Age Museum are just a couple of attractions that lure visitors to this fantastic city, so add them to your itinerary.

Where should I stay when visiting Lenox?

If you're after someplace comfortable to spend your nights, check out the The Yankee, Trademark Collection by Wyndham. It's the top choice for many visitors.