Lenox Vacation Packages 2026 from $692

Lenox flight + hotel vacation packages

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

The Yankee Inn

$692

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Holiday Inn Club Vacations Oak 'n Spruce Resort

$748

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.

Brook Bound Inn

$901

per person

Oct 11 - Oct 15

found 3 hours ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.

Aspen At Manchester

$836

per person

Oct 11 - Oct 15

found 3 hours ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.

The Wilmington Inn

$1,174

per person

Oct 11 - Oct 15

found 3 hours ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. A lobby fireplace, a library, and a picnic area are also on offer.

Top Lenox hotels deals

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$86 nightly

$97 total

Sep 28 - Sep 29

Total with taxes and fees

Pool

Hot Tub

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$162 total

Sep 28 - Sep 29

Total with taxes and fees

A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.

Pet friendly

Parking included

The Whitlock

16 Church St Lenox MA

$144 nightly

$160 total

Sep 9 - Sep 10

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.

Parking included

Free WiFi

The Cornell Inn, Lenox & The Berkshires

203 Main St Lenox MA

Free Cancellation

Reserve now, pay when you stay

$212 nightly

$236 total

Sep 3 - Sep 4

Total with taxes and fees

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

Breakfast included

Parking included

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$135 total

Sep 30 - Oct 1

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$198 total

Sep 7 - Sep 8

Total with taxes and fees

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Parking included

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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.

Stay near popular Lenox attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 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.

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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 $692. 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 120 mi 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 45 mi southeast of inner Lenox. Albany Intl. Airport (ALB) (40 mi away from central Lenox) and Hartford, CT (HFD-Hartford - Brainard) (55 mi 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.