A river with a city skyline in the background, including a prominent skyscraper and a bridge.

Lenox Hill Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Lenox Hill Vacation

Lock in a Lenox Hill vacation package and get ready to experience the best of this lively city. Think about staying in the neighborhood of Midtown East, which is good for shopping, cafes and nightlife. Love to explore your surroundings? Times Square, Rockefeller Center and Broadway are a few of the most popular places to visit during your trip to Lenox Hill. Don't put off exploring this destination any longer. Your dream Lenox Hill vacation is just a few clicks away with Expedia.

The Latest Lenox Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 22 - Jan 25

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $1,864
    CA $1,136
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • Jan 25 - Jan 28

    The St. Regis New York + Flight

    Manhattan
    3 nights
    5.0 star property
    9.2/10 - Wonderful (295 reviews)
    "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $3,702
    CA $1,939
    per traveller
    found 1 day ago
    The St. Regis New York
  • Dec 20 - Dec 24

    Eurostars The Chemists’ Club Hotel + Flight

    Manhattan
    4 nights
    4.0 star property
    9.4/10 - Exceptional (567 reviews)
    "Very convenient location. Good sized rooms."
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $3,020
    CA $1,759
    per traveller
    found 1 day ago
    Eurostars The Chemists’ Club Hotel
  • Dec 16 - Dec 20

    1 Hotel Brooklyn Bridge + Flight

    Brooklyn
    4 nights
    5.0 star property
    9.2/10 - Wonderful (1,002 reviews)
    "Incredible views, ambiance, staff, and overall experience! The only thing to note is that it can be quite loud since you're right on the waterfront and the ferries and boats sound their horns frequently"
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $4,812
    CA $2,989
    per traveller
    found 1 day ago
    1 Hotel Brooklyn Bridge
  • Feb 4 - Feb 7

    Mandarin Oriental, New York + Flight

    Manhattan
    3 nights
    5.0 star property
    9.2/10 - Wonderful (677 reviews)
    "Excellent stay"
    Reviewed October 26, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $3,333
    CA $2,079
    per traveller
    found 19 hours ago
    Mandarin Oriental, New York

Where to stay in Lenox Hill

Find the best Lenox Hill areas and neighborhoods for the activities you enjoy most.

Brooklyn

This bustling borough has everything — from pizza slices and pretzel vendors, to trendy galleries, and vintage stores -- all with killer views of the Manhattan skyline.

Midtown

Central portion of NYC, Midtown Manhattan boasts iconic landmarks like the Empire State Building and Times Square. Explore Broadway, Koreatown, and enjoy easy access to major transportation hubs like Grand Central Terminal.

Bronx

New York’s northernmost borough is one of its most diverse, featuring beautiful natural spaces alongside engaging history and the rousing spirit of its residents.

Williamsburg

Experience contemporary art, hipster culture, and vibrant nightlife in this Brooklyn gem. Discover cutting-edge galleries, trendy bars, and eclectic eateries for a taste of modern urban living.

Central New York City

Known for its soaring skyscrapers and eye-catching views, there's plenty to explore in Central New York City. Check out top attractions like Times Square and Rockefeller Center, and jump on the metro at 49th St. Station or 50 St. Station (Broadway) to see more of the city.

Discover the most popular places to visit in Lenox Hill

What to do near Lenox Hill

Lenox Hill Hotel Deals

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.

Frequently Asked Questions

How much does a Lenox Hill vacation package cost?

From as low as CA $1,136. Yes, you read that correctly. Our Lenox Hill packages are an easy way to make your dollars go much further. Combine your favorite flights, hotels and rental car and get out and explore this exciting destination.

How do I get a cheap travel package to Lenox Hill?

One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we've got them all. Pick and choose a combination that suits you and watch your savings grow. Of course, a package deal is never one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 hotel options across the globe, which lets you customize your Lenox Hill vacation.

Where should I stay in Lenox Hill?

A visit to Lenox Hill isn't over until you've seen Grand Central Terminal and United Nations Headquarters. Look for somewhere to stay nearby for easy access to these famous tourist attractions.

What are the top hotels in Lenox Hill?

Get your trip off to a flying start by reserving a room at 346 East 65th St 4b - 1 Bedroom Apts. It's one of most popular hotels in Lenox Hill. Another top option is 346 East 65th Street 5a 155 - 2 Bedroom Apts.

How far in advance should I book my Lenox Hill vacation?

While prices change from time to time, we generally suggest reserving your seat as early as possible. Many international airfares can be found on Expedia up to 12 months in advance. If you're booking last minute, you might still get lucky. Cheap tickets to Lenox Hill occasionally appear in the weeks prior to departure.

What does an Expedia Lenox Hill travel package include?

Car rentals, hotels and flights — we connect you to the very best bargains. All you have to do is pick and choose your preferred combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to put together an exciting Lenox Hill escape.

What should I know before booking a Lenox Hill travel package?

You'll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and unlock great discounts. You're not limited to hotels, however. We have oceanfront condos, city apartments and even glamping tents!

Can I choose my airline with a Lenox Hill Expedia vacation package?

With a vacation package, you're the one in charge. Whether you want to fly to Lenox Hill in business or coach, simply select from the available airline options. Expedia has access to over 550 airline partners throughout the world.

If I'm not able to travel, can I cancel my Lenox Hill vacation package?

It's difficult to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Lenox Hill vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

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