Westchester County Holidays
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Top destinations in Westchester County
Top Flight + Hotel Deals in Westchester County
Price found within the past 48 hours. Click for updated prices.
The William Hotel Midtown, New York
Manhattan
€2,747
per person
1 Dec - 6 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (258 reviews)
Very interesting place. Unassuming on 39th Street but reasonably priced and quite a large room. Very charming with a lot of character and history. The bar was great.
Reviewed on 19 Oct 2026
Top hotels in Westchester County
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
€137
1 Nov - 2 Nov
includes taxes & fees
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
€184
8 Nov - 9 Nov
includes taxes & fees
8.2/10 Very good! (1,375 reviews)
"I was handed a map to my room when checking in that wasn’t very helpful. I had to hoist my own luggage down 2 flights of stairs and try to locate an elevator down another flight. If it wasn’t for some kids running in the halls who helped me find my way through the maze, I wouldn’t have found it. ..."
Reviewed on 21 Oct 2026
Sleepy Hollow Hotel, a Dolce by Wyndham
455 S Broadway Tarrytown NY
Fully refundableReserve now, pay when you stay
€146
1 Nov - 2 Nov
includes taxes & fees
7/10 Good! (1,020 reviews)
"Didn’t like the fact that there no heat in our room and was told that the isn’t turned on this time of the year"
Reviewed on 21 Oct 2026
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 holiday package cost?
We make it easy to explore the world, with Westchester County holiday packages starting from as little as €1,845. 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 travellers.
How far in advance should I book my Westchester County holiday?
It can be tricky to know exactly when is the ideal time to book your holiday 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 favourite 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 organising 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 holiday package is the easiest way to organise 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 holiday 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 holiday 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 holiday 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 gavvykins
Capitol Theatre
7.4/10 (117 reviews)
Enjoy a show at Capitol Theatre, a theatre with a story to tell in Port Chester. Discover the entertainment choices and shops in this family-friendly area.
Photo by Jeff White
Lyndhurst Mansion
8.6/10 (130 reviews)
Learn about the local history of Tarrytown when you spend time at Lyndhurst Mansion. Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.
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.
Empire City Casino
8.0/10 (249 reviews)
Why not roll the dice with a visit to Empire City Casino during your travels in Yonkers? Experience the acclaimed art galleries and fascinating museums in this vibrant area.
New Roc City
8.4/10 (99 reviews)
You can find the perfect gifts to bring home at New Roc City during your visit to New Rochelle. Amble around the area's picturesque gardens or attend a sporting event.
The Westchester Mall
9.0/10 (231 reviews)
During your trip to White Plains, you can find the perfect gifts to bring home at The Westchester Mall. Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.
Tarrytown Music Hall
8.4/10 (129 reviews)
Enjoy a performance at Tarrytown Music Hall, a popular theatre in Tarrytown. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.
Westchester's Ridge Hill
8.8/10 (217 reviews)
You can find the perfect gifts to bring home at Westchester's Ridge Hill during your visit to Yonkers. Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.
What to do in Westchester County
9/11 Memorial & Ground Zero Walking Tour with Museum Option
€21
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
