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*
  • 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 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 Shelburne Sonesta New York + Flight

    Manhattan
    3 nights
    4.0 star property
    9.0/10 - Wonderful (2,052 reviews)
    "This is our go-to midtown hotel. Love the location. Rooms are generally more spacious. Accommodations are up to date. Staff is kind, fun and helpful. Rooftop restaurant is fabulous."
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,581
    CA $1,075
    per traveller
    found 1 day ago
    The Shelburne Sonesta 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 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
  • Jan 10 - Jan 15

    The Gardens Sonesta ES Suites New York + Flight

    Manhattan
    5 nights
    3.0 star property
    9.0/10 - Wonderful (1,003 reviews)
    "Staff was very friendly and helpful. This was one of the most affordable places close to Cental Park. Great dining and coffee/bagel shops. Nice kitchennet with stovetop, microwave, and dishes for two, for a longer term stay. Nice complimentary coffee bar with cappuccinos, lattes, and tea."
    Reviewed November 6, 2026
    Roundtrip • Montreal (YUL) - New York (JFK)
    YUL - LGA • 1 stop LGA - YUL • 1 stop
    CA $2,622
    CA $1,757
    per traveller
    found 1 day ago
    The Gardens Sonesta ES Suites New York
  • Dec 11 - Dec 13

    Eurostars Wall Street + Flight

    Manhattan
    2 nights
    4.0 star property
    8.0/10 - Very good (1,001 reviews)
    "Cons: Air conditioning never really worked well. Thankfully opening the window helped. It's kind of set up like an apartment so there isn't an ice machine on the floor. The TV was tiny and hard to watch. Breakfast wasn't complimentary ($19 per person). IDK for $2200 I expected a higher caliber of service and amenities. Pros: The staff was always helpful. The location is convenient especially for things downtown close the the financial district."
    Reviewed November 3, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,696
    CA $1,157
    per traveller
    found 1 day ago
    Eurostars Wall Street

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 $1,075. 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.