Cheap Flight Deals to Lenox MA from CA $103

Feel at ease with free flight cancellations within 24 hours of booking

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How to find cheap flights to Lenox?

The cheapest prices found with in the last 7 days for return flights were CA $208 and CA $103 for one-way flights to Lenox for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
FLLLathamSeptember 27 to September 28CA $208
MCOLathamDecember 7 to December 14CA $267
DENLathamOctober 14 to October 15CA $443
LAXLathamOctober 3 to October 7CA $750
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLLathamSeptember 27 to September 28CA $208
*Prices include taxes and fees

Your guide to flights to Lenox, MA

JetBlue Airways, Delta fly to Lenox, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Lenox MA currently costs between CA $208 and CA $750. Prices vary, but for the best fares, travel in September when prices are at their lowest.  

Top tips for finding cheap flights to Lenox  

The cheapest flight for a round trip to Lenox is currently CA $208. When you search for flights to Lenox, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Lenox for nearby days.  The cheapest month to travel to Lenox is September from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Lenox 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Lenox with Travelocity 

We have top deals on plane tickets even for last minute flights to Lenox, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Lenox for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Lenox

Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
The price is CA $95 per night from Sep 27 to Sep 28
CA $95
CA $106 total
Sep 27 - Sep 28
includes taxes & fees
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
7/10 Good! (626 reviews)
"And I mean the David Lynch as a compliment."

Reviewed on Aug 14, 2025

Opens in a new windowWagon Wheel Inn
Lenox Inn

Lenox Inn

2 out of 5
Pittsfield Road,525, Lenox, Massachusetts
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tanglewood Music Center and Guido's Marketplace are located ...
"Sadly, this place is about 40 years out of date. Heat, electrical, shower, bathroom fixtures all badly out of date. The beds are like a pile of sand. Really harsh. You get what you pay for, except this place should cost half again what they charge. Sorry, but it's the truth"

Reviewed on Feb 3, 2020

Opens in a new windowLenox Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is CA $109 per night from Sep 28 to Sep 29
CA $109
CA $122 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (802 reviews)
"Great place to stay for overnight stays. Breakfast was appreciated."

Reviewed on Sep 15, 2025

Opens in a new windowHoward Johnson by Wyndham Lenox
Save an average of 15% on thousands of hotels when you're signed in
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is CA $163 per night from Oct 1 to Oct 2
CA $163
CA $182 total
Oct 1 - Oct 2
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 ...
9/10 Wonderful! (1,004 reviews)
"With spa, fireplace and canopy over the bed it was the perfect treat for myself!"

Reviewed on Sep 16, 2025

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
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.

Luxury Hotels in Lenox

Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
The price is CA $95 per night from Sep 27 to Sep 28
CA $95
CA $106 total
Sep 27 - Sep 28
includes taxes & fees
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
7/10 Good! (626 reviews)
"And I mean the David Lynch as a compliment."

Reviewed on Aug 14, 2025

Opens in a new windowWagon Wheel Inn
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is CA $163 per night from Oct 1 to Oct 2
CA $163
CA $182 total
Oct 1 - Oct 2
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 ...
9/10 Wonderful! (1,004 reviews)
"With spa, fireplace and canopy over the bed it was the perfect treat for myself!"

Reviewed on Sep 16, 2025

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is CA $109 per night from Sep 28 to Sep 29
CA $109
CA $122 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (802 reviews)
"Great place to stay for overnight stays. Breakfast was appreciated."

Reviewed on Sep 15, 2025

Opens in a new windowHoward Johnson by Wyndham Lenox
Save an average of 15% on thousands of hotels when you're signed in
Lenox Inn

Lenox Inn

2 out of 5
Pittsfield Road,525, Lenox, Massachusetts
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tanglewood Music Center and Guido's Marketplace are located ...
"Sadly, this place is about 40 years out of date. Heat, electrical, shower, bathroom fixtures all badly out of date. The beds are like a pile of sand. Really harsh. You get what you pay for, except this place should cost half again what they charge. Sorry, but it's the truth"

Reviewed on Feb 3, 2020

Opens in a new windowLenox Inn
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.

Family Friendly Hotels in Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
The price is CA $186 per night from Sep 25 to Sep 26
CA $186
CA $208 total
Sep 25 - Sep 26
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 ...
9/10 Wonderful! (1,003 reviews)
"We enjoyed the quietness of the hotel and breakfast. It is very conveniantly located on RTR7/US20 but tucked off the road so its quiet"

Reviewed on Sep 16, 2025

Opens in a new windowHampton Inn & Suites Berkshires-Lenox
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is CA $163 per night from Oct 1 to Oct 2
CA $163
CA $182 total
Oct 1 - Oct 2
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 ...
9/10 Wonderful! (1,004 reviews)
"With spa, fireplace and canopy over the bed it was the perfect treat for myself!"

Reviewed on Sep 16, 2025

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is CA $109 per night from Sep 28 to Sep 29
CA $109
CA $122 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (802 reviews)
"Great place to stay for overnight stays. Breakfast was appreciated."

Reviewed on Sep 15, 2025

Opens in a new windowHoward Johnson by Wyndham Lenox
Save an average of 15% on thousands of hotels when you're signed in
Lenox Inn

Lenox Inn

2 out of 5
Pittsfield Road,525, Lenox, Massachusetts
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tanglewood Music Center and Guido's Marketplace are located ...
"Sadly, this place is about 40 years out of date. Heat, electrical, shower, bathroom fixtures all badly out of date. The beds are like a pile of sand. Really harsh. You get what you pay for, except this place should cost half again what they charge. Sorry, but it's the truth"

Reviewed on Feb 3, 2020

Opens in a new windowLenox Inn
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.

Best Lenox Flight and Hotel Packages

Lenox flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views
Kingston Carriage House
The Hideout Catskills Cottage
Don't see what you're looking for?
See all available trips from Toronto to Lenox
View all trips

Lenox flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Albany Airport
The Century House, an Ascend Collection Hotel
Hampton Inn Albany-Wolf Road (Airport)
Don't see what you're looking for?
See all available trips from Quito to Lenox
View all trips

Need a car after flight to Lenox?

Plane Tickets To Lenox

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Lenox. Browse through our inventory to explore a wide range of cheap flights to Lenox to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Lenox as you anxiously await to exit the plane and explore what Lenox has to offer. Considering all the amazing local food and culture in Lenox, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Lenox to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Lenox without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Lenox with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Lenox today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.