Westchester County Holidays

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Top destinations in Westchester County

A waterfront path with a bike lane, autumn foliage, and a city skyline in the background.

Yonkers

Yonkers
A cityscape with modern buildings, a large parking structure, and a river in the background.

White Plains

White Plains
A wooden boardwalk winding through a forest with autumn foliage.

Ossining

Ossining

Our pick of the best Westchester County Hotel Deals

Tarrytown House Estate

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
NZ$391
7 Sept - 8 Sept
includes taxes & fees
Tarrytown House Estate
Royal Regency Hotel

Royal Regency Hotel

165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
NZ$258
28 Sept - 29 Sept
includes taxes & fees
Royal Regency Hotel
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
NZ$220
13 Sept - 14 Sept
includes taxes & fees
Hampton Inn White Plains/Tarrytown
See all 530 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.

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 . 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

A large, historic stone building with multiple chimneys and arched windows.
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.
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A band performing on stage with a large screen displaying a woman's face in the background.
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.
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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.
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Rye Playland

8.2/10 (33 reviews)
Enjoy a fun-filled day at Rye Playland during your visit to Rye. Discover the live music in this family-friendly area or seek out its hiking trails.
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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.
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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.
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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.
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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.
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What to do in Westchester County

Bronx Zoo Admission Ticket

Bronx Zoo Admission Ticket

NZ$74
per adult
88% of travellers recommend
Bronx Zoo Admission Ticket
Outside the Yankee Stadium Hard Rock Cafe in New York

Dining at Hard Rock Cafe Yankee Stadium

NZ$67
per traveller
Dining at Hard Rock Cafe Yankee Stadium
Autumn Glow Festival Chinese Lantern Light Walk in Schenectady

Autumn Glow Chinese Lantern Festival Mabee Farm and Glen Island

NZ$35
per adult
Autumn Glow Chinese Lantern Festival Mabee Farm and Glen Island
See all activities in Westchester County

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