Westchester County Vacations & Trips from ￥272,008
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Top destinations in Westchester County
White Plains
The Latest Westchester County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Library Hotel by Library Hotel Collection
Manhattan
￥337,680
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.6/10 Exceptional! (1,008 reviews)
Wonderful hotel just off Bryant Park. Walking distance to Broadway and Central Park. Rooms for very cozy and the staff was very friendly. Continental breakfast was good. We’ll stay here again… just double check size of bed when you book, it could be smaller than you think?
Reviewed on Aug 31, 2026
Margaritaville Resort Times Square
Manhattan
￥329,986
per person
Nov 3 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to New York (JFK)
9/10 Wonderful! (4,314 reviews)
The staff was very friendly! The room was Immaculate. The hotel overall was very nice. However I was very disappointed upon check in .. I found out that the pool was closing early as well as the restaurant due to a private event! I was planning my evening to relax at the pool and eat at the restaurant.. that was one of the the main reasons I book that particular hotel for the pool experience.. I was only there one night.. so was unable to enjoy the next evening..
Reviewed on Sep 1, 2026
42 Hotel
￥295,390
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (960 reviews)
I have never stayed at a hotel where the staff was so absolutely amazing!! The location was ideal: quiet enough to get a good night's sleep or an afternoon nap, but close enough to the subway and many restaurants for that big city adventure.
Reviewed on Sep 1, 2026
Westchester County Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
￥25,407
￥33,055 total
Sep 2 - Sep 3
includes taxes & fees
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
￥20,134
￥24,506 total
Sep 28 - Sep 29
includes taxes & fees
8.6/10 Excellent! (2,851 reviews)
"Great staff"
Reviewed on Sep 1, 2026
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
￥18,082
￥20,680 total
Sep 13 - Sep 14
includes taxes & fees
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 ￥272,008. 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.
Stay near popular Westchester County attractions
Photo by Jeff White
Lyndhurst Mansion
8.6/10 (130 reviews)
Learn about the local history of Tarrytown with a stop at Lyndhurst Mansion. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.
Photo by gavvykins
Capitol Theatre
7.4/10 (117 reviews)
Enjoy a show at Capitol Theatre, a theater with a story to tell in Port Chester. Discover the entertainment choices and shops in this family-friendly area.
Westchester County Center
8.0/10 (133 reviews)
Enjoy a stop at Westchester County Center, an entertaining place to visit in White Plains. Wander the riverfront in this family-friendly area.
Rye Playland
8.2/10 (33 reviews)
Have a fun-filled day with the family at Rye Playland during your visit to Rye. Discover the live music in this family-friendly area, or seek out its hiking trails.
The Westchester Mall
9.0/10 (231 reviews)
During your trip to White Plains, you can do some window-shopping at The Westchester Mall. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.
Empire City Casino
8.0/10 (249 reviews)
Why not roll the dice with a visit to Empire City Casino during your time in Yonkers? Experience the fascinating museums and acclaimed art scene in this vibrant area.
Tarrytown Music Hall
8.4/10 (129 reviews)
Enjoy a performance at Tarrytown Music Hall, a storied theater in Tarrytown. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.
New Roc City
8.4/10 (99 reviews)
You can search for that perfect souvenir at New Roc City during your trip to New Rochelle. Amble around the area's picturesque gardens or attend a sporting event.
What to do in Westchester County
New York Mets Baseball Game at Citi Field
￥4,376
per adult
100% of travellers recommend
LEGOLAND® Discovery Center Westchester Tickets
￥4,863
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
