A lighthouse, a metal bridge, and calm water at sunset.

Westchester County 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*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Westchester County Vacation

Leave the planning up to us with a Westchester County vacation package. With everything organized before you leave, the only thing you'll need to do is relax and enjoy this destination's countless delights. A trip to Westchester County wouldn't be complete without experiencing some of its best cities, starting with Yonkers. Two of the top attractions here include Yankee Stadium and Bronx Zoo. Peekskill is another favourite with Westchester County travellers. Visitors to this exciting city love Van Cortlandt Manor and Michie Stadium. Start packing your suitcase, because your Westchester County vacation is just clicks away with Expedia.

Top destinations in Westchester County

The Latest Westchester County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 13 - Dec 16

    The Inn At Fox Hollow Hotel + Flight

    Woodbury
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,002 reviews)
    "Clean and comfortable"
    Reviewed November 2, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,229
    CA $798
    per traveller
    found 2 days ago
    The Inn At Fox Hollow Hotel
  • Jan 14 - Jan 17

    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)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $2,033
    CA $1,114
    per traveller
    found 2 days ago
    JW Marriott Essex House New York
  • Jan 10 - Jan 15

    Eurostars The Chemists’ Club Hotel + Flight

    Manhattan
    5 nights
    4.0 star property
    9.4/10 - Exceptional (564 reviews)
    Roundtrip • Montreal (YUL) - New York (JFK)
    YUL - LGA • 1 stop LGA - YUL • 1 stop
    CA $2,739
    CA $1,621
    per traveller
    found 1 day ago
    Eurostars The Chemists’ Club Hotel
  • Dec 23 - Dec 28

    1 Hotel Central Park + Flight

    Manhattan
    5 nights
    5.0 star property
    9.0/10 - Wonderful (1,004 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $4,385
    CA $2,813
    per traveller
    found 2 days ago
    1 Hotel Central Park
  • Dec 30 - Jan 2

    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)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $5,180
    CA $3,335
    per traveller
    found 1 day ago
    Mandarin Oriental, New York

Discover the most popular places to visit in Westchester County

What to do in Westchester County

Westchester County 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 Westchester County vacation package cost?

We make it easy to explore the world, with Westchester County vacation packages starting from as little as CA $798. You'll have the flexibility to bundle your preferred hotels, airlines and car rental. For the ultimate getaway, why not add a couple of tours and experiences to your travel itinerary?

How do I get a cheap travel package to Westchester County?

You'll save big if you combine your flights, hotels and car rentals into a Westchester County travel package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 air carriers and 1,000,000 properties throughout the world, so you'll always have plenty of variety to choose from. Eager to save even more? Add some popular activities to your package deal and unlock even bigger bargains! After all, travel is about more than just getting to your destination.

Where should I stay in Westchester County?

Sarah Lawrence College is one of the many things that draws people to Westchester County, so it's no surprise that many decide to book a hotel in White Plains.

What are the top hotels in Westchester County?

Royal Regency Hotel and Tru By Hilton Albany Airport, NY know how to make their guests feel at home in Yonkers. If your itinerary also includes White Plains, look up Courtyard by Marriott Yonkers Westchester County and Baymont by Wyndham White Plains - Elmsford. Both are popular with travelers.

How far in advance should I book my Westchester County vacation?

It can be tricky to know exactly when is the ideal time to book your vacation to Westchester County. But generally the earlier you book, the more affordable the prices. Sometimes, you can secure your flights and hotels nearly a year before your departure date. If you're eager to escape on a last-minute getaway, no need to panic! There are fantastic bargains popping up on Expedia every single day.

What does an Expedia Westchester County travel package include?

Flights, hotels and a cool car for your road trip adventures. Simply mix and match your favorite bundle and gain access to great discounts. Once you've made your booking, add on a few sightseeing tours and watch your savings grow. When it comes to organizing your Westchester County break, you're in control!

What should I know before booking a Westchester County travel package?

Bundling your bookings into a Westchester County vacation package is the easiest way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?

Can I choose my airline with a Westchester County Expedia vacation package?

Most definitely. Expedia has over 550 partner airlines to choose from around the world. With all that choice, finding the right carrier to whisk you off to Westchester County will be a breeze.

If I'm not able to travel, can I cancel my Westchester County vacation package?

Yes, you can. We totally understand that life doesn't always go to plan, so we're here to help if you need to make changes to your Westchester County vacation package. It may be possible to cancel or change your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the nitty-gritty on change fees.

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