Westchester County Vacations & Trips from $456

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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

The Latest Westchester County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel
1 Hotel Brooklyn Bridge
Loews Regency New York Hotel
Sound View Greenport
Hyatt Regency Jersey City on the Hudson

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

Frequently asked questions

How much does a Westchester County vacation package cost?
Perhaps less than you might think — from as low as $456, 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.
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Explore a world of travel with Expedia

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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.