Westchester County Vacations & Trips from $780

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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 favorite with Westchester County travelers. 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

A red brick building with blue trim, a green SUV, and a red car parked in front.

Tarrytown

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

White Plains

White Plains
A coastal cityscape with residential areas, a large body of water, and prominent skyscrapers.

New Rochelle

New Rochelle
A wooden fence, tall grasses, and a body of water under a cloudy sky.

Rye

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

Yonkers

Yonkers
A calm lake with a forested island in the distance, a picnic area, and a rocky shoreline.

Peekskill

Peekskill
A lighthouse on a small island with a bridge in the background.

Elmsford

Elmsford
A residential area with houses, streets, and trees.

Mount Vernon

Mount Vernon
A wooden boardwalk winding through a forest with autumn foliage.

Ossining

Ossining

The Latest Westchester County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Lotte New York Palace

Lotte New York Palace

Manhattan
$780
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,230 reviews)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

North End
Save 100% on your flight
$878
per person
Oct 30 - Nov 1
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
No reviews
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

Manhattan
Save 100% on your flight
$1,647
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,331 reviews)
Clean property. Staff was helpful. The breakfast was a nice buffet but crowded.

Reviewed on Sep 10, 2026

Seven Beach Lane

Seven Beach Lane

Save 100% on your flight
$793
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.4/10 Exceptional! (34 reviews)
Las Flores Villa

Las Flores Villa

$4,815
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
10/10 Exceptional! (1 review)

Best Places to Vacation in Westchester County

1. Book your ideal Yonkers with a vacation package

Yonkers, located in New York, offers a diverse range of experiences for a family-friendly vacation. The city boasts a vibrant shopping scene, with plenty of options for dining and cafes. The friendly locals and beautiful river and gardens create a welcoming atmosphere. Outdoor enthusiasts will enjoy hiking opportunities, while business and entertainment options cater to all interests. Whether you're looking for destination activities or simply want to explore the local area, Yonkers has something for everyone to enjoy.

  • The peak season is from March to May
  • The off-peak season is from October to December
  • Travelers tend to stay 2 days in Yonkers

2. Discover White Plains with our vacation deals

White Plains, located in New York, offers a diverse range of activities for a family vacation. From shopping and dining to wildlife and historical sites, there is something for everyone. The city has a vibrant atmosphere with plenty of entertainment options, including live music and cafes. Whether you're interested in business or hiking, White Plains has it all. Popular activities for travelers include destination activities and various things to do. With its geographic affinities, White Plains is the perfect destination for a memorable family vacation.

  • Travelers tend to stay 2 days in White Plains

3. Plan your dream getaway to Tarrytown

Tarrytown, located in New York, offers a unique atmosphere and experience for a family vacation. With its charming cafes, friendly people, and historical sites, it is a perfect destination for those seeking a relaxing and educational getaway. Explore the local river and enjoy scenic views, or indulge in the diverse dining options available. Tarrytown also offers shopping opportunities and various tours to learn more about the area's rich history. Don't miss the chance to visit the famous castle and engage in family-friendly activities. Whether you're looking for adventure or relaxation, Tarrytown has something to offer for everyone.

  • The peak season is from July to September
  • The off-peak season is from November to January
  • Travelers tend to stay 2 days in Tarrytown

4. Find your perfect New Rochelle vacation

New Rochelle, located in New York, offers a diverse range of experiences for families on vacation. With its beautiful islands, delicious dining options, and family-friendly atmosphere, there is something for everyone to enjoy. Shopping enthusiasts will appreciate the variety of stores available, while wildlife and flower lovers can explore the natural beauty of the area. For those interested in hunting and birdwatching, New Rochelle provides ample opportunities. The friendly people add to the welcoming atmosphere of the city, making it a great destination for a family vacation. There are plenty of activities and things to do to keep everyone entertained throughout their stay.

  • The peak season is from February to April
  • The off-peak season is from October to December
  • Travelers tend to stay 2 days in New Rochelle

6. Enjoy Elmsford with a travel package

Elmsford, located in New York, offers a great atmosphere for a family vacation. With its beautiful wildlife and scenic landscapes, it's perfect for outdoor enthusiasts. The town also boasts a variety of dining options, from cozy cafes to family-friendly restaurants. If you're in the mood for shopping, Elmsford has plenty of stores to explore. The locals are known for their friendliness and welcoming nature, making your stay even more enjoyable. Plus, Elmsford is budget-friendly, allowing you to have a memorable vacation without breaking the bank. Whether you're taking a leisurely walk or grabbing a cup of coffee, Elmsford has something for everyone.

  • The peak season is from March to May
  • The off-peak season is from November to January
  • Travelers tend to stay 2 days in Elmsford

5. Create memories in Peekskill with a vacation package

Peekskill, located in New York, offers a diverse range of outdoor vacation experiences. Whether you're looking to explore the nearby mountains and go hiking, enjoy family-friendly activities, or relax by the river, Peekskill has something for everyone. The local atmosphere is friendly and welcoming, with plenty of dining options to satisfy your taste buds. You can also embark on excursions to explore the surrounding areas. Whether you're here for business or pleasure, Peekskill provides a perfect blend of adventure and relaxation. Don't miss the chance to experience the vibrant atmosphere and friendly people of this charming town.

  • The peak season is from July to September
  • The off-peak season is from November to January
  • Travelers tend to stay 2 days in Peekskill

Things to do in Westchester County

Westchester County, New York, offers a delightful mix of activities perfect for families and couples alike. Enjoy shopping at various centers, catch a show at local theaters, or indulge in a romantic getaway. Explore outdoor attractions and unwind at wellness retreats, or embark on a scenic wine tour to savor local flavors. With its vibrant city vibe and beautiful landscapes, Westchester County is an ideal destination for diverse vacation experiences.

Shopping

In Westchester County, you can shop at The Westchester Mall for high-end brands and entertainment. Westchester's Ridge Hill offers a mix of dining and shopping, while New Roc City combines retail with fun activities for the whole family. Enjoy a vibrant shopping experience at these locations.

Recreation

The Capitol Theatre offers an enchanting atmosphere for cultural experiences, blending romance and family-friendly entertainment. Tarrytown Music Hall is a hub for lively concerts, providing a vibrant backdrop for music lovers. Harbor Island Park is perfect for relaxation, with scenic views and tranquil spaces for rejuvenation.

Adventure

Experience the thrill of Legoland Discovery Center Westchester, where you can explore interactive exhibits and enjoy arcade games. For adrenaline seekers, Grand Prix New York offers exciting karting races, while New Roc n Bowl combines bowling and arcade fun for an adventurous day out with family and friends.

Nightlife

For vibrant nightlife in Westchester County, visit New Rochelle and White Plains, where bustling bars and lounges offer live music and dancing. Enjoy craft cocktails at trendy spots in Yonkers and catch a show at the Tarrytown Music Hall for a memorable night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Westchester County

Westchester County offers a perfect blend of family-friendly activities, outdoor adventures, and urban exploration. Visitors can enjoy cultural experiences at historic buildings and modern universities, while attractions like the Westchester Mall and Riverwalk provide shopping and scenic views. For a romantic getaway, discover charming spots throughout the area. Whether you're seeking relaxation or excitement, Westchester County has something for everyone.

  • Rye Playland: Experience the charm of this historic amusement park, featuring classic rides and modern attractions. With its family-friendly atmosphere, beautiful waterfront views, and thrilling roller coasters, Rye Playland is perfect for adventure seekers and families alike, ensuring a fun-filled day for all ages.
  • Westchester County Center: Immerse yourself in the local arts scene at this cultural hub, hosting a variety of events including concerts, exhibitions, and fairs. The venue's vibrant atmosphere and diverse programming make it an essential stop for art lovers and those looking to experience the region's rich cultural offerings.
  • Sarah Lawrence College: Explore this picturesque campus known for its liberal arts education and innovative programs. The beautiful grounds and modern architecture create a unique environment that fosters creativity and intellectual exploration, making it an inspiring place to visit.

Tips to save on your trip to Westchester County

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Westchester County.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Westchester County.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Find the Best Westchester County Vacation Packages

Westchester County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Top Sights
Franklin D. Roosevelt State Park, Glen Island Park and Untermyer Gardens Conservancy

Westchester County Hotel Deals

Tarrytown House Estate

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$181 nightly
$207 total
Sep 13 - Sep 14
Total with taxes and fees
8.2/10 Very Good! (1,289 reviews)
"Very far distance from parking to rooms and lots of areas with only steps not elevators. Hard work carrying bags in if you are staying in certain areas. Otherwise very nice place."

Reviewed on Sep 10, 2026

Tarrytown House Estate
Royal Regency Hotel

Royal Regency Hotel

165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
$120 nightly
$142 total
Oct 4 - Oct 5
Total with taxes and 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
$118 nightly
$135 total
Sep 20 - Sep 21
Total with taxes and fees
Hampton Inn White Plains/Tarrytown
See all 524 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?
Perhaps less than you might think — from as low as $780, as a matter of fact! By bundling hotels, flights and car rentals into a customized package, your Westchester County escape is just clicks away.
How do I get a cheap travel package to Westchester County?
Bundle your bookings with Expedia to save big bucks on your next getaway. With more than 550 partner airlines and 1,000,000 hotel options globally, your Westchester County vacation package can be tailored exactly to suit your travel style. With all those extra dollars, why not add some exciting experiences and tours? It's an easy way to unlock even more savings. Your dream getaway to Westchester County is closer than you thought!
Where should I stay in Westchester County?
Yankee Stadium is one of the things that attracts travelers to Westchester County, so it makes perfect sense that many get a hotel in Maryknoll.
What are the top hotels in Westchester County?
Royal Regency Hotel and Courtyard by Marriott Yonkers Westchester County know how to make their guests feel at home in Yonkers. If you also plan to get to White Plains, look up Hampton Inn & Suites Yonkers and Hampton Inn White Plains/Tarrytown. Both are top picks with travelers.
How far in advance should I book my Westchester County vacation?
Reserving your tickets early with Expedia means one less thing to worry about. Most carriers display prices up to a year in advance. This is generally the cheapest time to book. If circumstances have left you booking late, incredible deals to Westchester County sometimes occur just weeks before departure.
What does an Expedia Westchester County travel package include?
That's up to you. You can pick from a range of Westchester County packages, such as a rental car, flight and hotel. You can also book a flight and a hotel, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like activities and experiences. Whatever your dream Westchester County escape looks like, you're sure to save!
What should I know before booking a Westchester County travel package?
Discover deals that match your budget with an Expedia package. Flights, hotels, rental cars — we're a one-stop shop for all of them. You'll save loads just by combining your bookings. Whether you're going on a ski adventure or sunning yourself on a warm beach, your ideal vacation is only a few clicks away.
Can I choose my airline with a Westchester County Expedia vacation package?
Yes, the choice is yours. Expedia has access to more than 550 partner airlines across the globe, so you can tailor your Westchester County vacation according to your budget and travel needs.
Does Expedia offer Book Now, Pay Later Westchester County vacation packages?
With a vacation package, you can customize both your getaway and a payment arrangement. Expedia can help reduce financial stress to do with your journey with a Book Now, Pay Later booking, thanks to us joining forces with online lender Affirm. That way, all you have to concentrate on is preparing to jet off into the sunset.
If I'm not able to travel, can I cancel my Westchester County vacation package?
If your vacation plans in Westchester County have changed, it's comforting to know that it's possible to amend or cancel your booking. If your booking was made less than 24 hours ago, you may be able to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge fees. For more details, check our Customer Service Portal.

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 with a stop at Lyndhurst Mansion. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.
See properties
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 theater 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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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 acclaimed art scene and fascinating museums in this vibrant area.
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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.
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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.
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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.
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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.
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What to do in Westchester County

Bronx Zoo Admission Ticket

Bronx Zoo Admission Ticket

$44
per adult
88% of travellers recommend
Bronx Zoo Admission Ticket
NYC Trolley Tour Explore Harlem The Bronx Queens and Brooklyn

NYC Trolley Tour Explore Harlem The Bronx Queens and Brooklyn

$69
per adult
NYC Trolley Tour Explore Harlem The Bronx Queens and Brooklyn
Private Central Park Adventure Tour

New York: Central Park Walking Personalized Self-Guided App Tour

$5
per adult
100% of travellers recommend
New York: Central Park Walking Personalized Self-Guided App Tour
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.