Westchester County Vacation Packages

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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 vacation destinations in Westchester County

A lit bridge at night with a river in the foreground and a cloudy sky.
FlightsFlightsHotelsHotels

Yonkers

Yonkers

Top Westchester County Vacation Deals

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

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,330, price is now CA $823 per person
CA $823
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,182 reviews)
Room was clean but very dated. Everything worked, however the outlets were few and one required repair. AC was loud and not sufficient to fully cool the room, but not terrible. Convenient to 96th Street subway. Staff was very friendly. Overall, a good experience.

Reviewed on Jun 22, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,871, price is now CA $1,825 per person
CA $1,825
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 2026

Hilton Garden Inn New York/Manhattan-Midtown East

Hilton Garden Inn New York/Manhattan-Midtown East

3.5 out of 5
Manhattan
Price was CA $1,613, price is now CA $1,034 per person
CA $1,034
per person
Sep 4 - Sep 7
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (1,761 reviews)
It was a very pleasant stay

Reviewed on Jun 17, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,570, price is now CA $1,046 per person
CA $1,046
per person
Sep 4 - Sep 7
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
Hotel was quaint and charming! The beds were comfortable and clean. Staff was super helpful and even let us borrow an umbrella and were really quick with food recommendations and subway directions! Loved our stay…would stay here again.

Reviewed on Jun 23, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,740, price is now CA $1,164 per person
CA $1,164
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
We usually stay at the Ritz but prices were up overall due to the World Cup so we tried this property. It was fantastic and we may have found a new favorite.

Reviewed on Jun 15, 2026

Westchester County Hotel Deals

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jun 28 to Jun 29
CA $203
CA $232 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (1,725 reviews)
"👍"

Reviewed on Jun 22, 2026

Baymont by Wyndham White Plains - Elmsford
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
The price is CA $256 per night from Jul 1 to Jul 2
CA $256
CA $340 total
Jul 1 - Jul 2
includes taxes & fees
8.8/10 Excellent! (1,323 reviews)
"Good breakfast bar, pleasant staff, clean and spacious rooms."

Reviewed on Jun 21, 2026

Sonesta White Plains Downtown
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Jun 30 to Jul 1
CA $185
CA $263 total
Jun 30 - Jul 1
includes taxes & fees
8.2/10 Very Good! (1,128 reviews)
"Staff at check in could have given better directions from parking lot 4 to our room, also better signage."

Reviewed on Jun 22, 2026

Tarrytown House Estate
See all 553 properties in Westchester County
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.
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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 $823. 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.