Westchester County Vacations & Trips from $676

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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

FlightsFlightsHotelsHotels

White Plains

White Plains

The Latest Westchester County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was $1,194, price is now $676 per person
$676
per person
May 18 - May 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,108 reviews)
Literally Times Square is a quick 1 minute walk from this hotel, comfy and quiet.

Reviewed on Apr 7, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $6,875, price is now $3,621 per person
$3,621
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (145 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower. But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker. Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door. It’s little odd things that just made it not feel like a luxury stay. And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use. The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.

Reviewed on Mar 24, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $1,860, price is now $1,076 per person
$1,076
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Fantastic staycation! The spa was awesome and experience overall was solid. Would definitely stay here again!

Reviewed on Mar 31, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $4,129, price is now $2,397 per person
$2,397
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
You book this hotel for the location. Amenities, service are ok. People are friendly and willing to help but some thing are just the way they are. AC don’t work all the time, when it did it produced a high pitched noise, there was this flashing light right above the bed that was seemingly random in its blinking pattern sometimes really bright other times not noticeable. Our first room had a view of construction equipment, second room on floor 10 was a lot better. TV stopped working after first night, two asks to fix nothing changed. It was really nice to be able to drink from the taps in the bathroom.

Reviewed on Mar 31, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $4,179, price is now $2,500 per person
$2,500
per person
May 22 - May 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews

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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $141 total per night from Apr 19 to Apr 20
$141 total
Apr 19 - Apr 20
Total with taxes and fees
8.2/10 Very Good! (1,636 reviews)
Not a good experience

Reviewed on Apr 7, 2026

Baymont by Wyndham White Plains - Elmsford
Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
160 Corporate Blvd Yonkers NY
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Apr 26 to Apr 27
$129 total
Apr 26 - Apr 27
Total with taxes and fees
8.4/10 Very Good! (1,815 reviews)
The kitchen was very clean, it had what we needed.

Reviewed on Apr 7, 2026

Hampton Inn & Suites Yonkers
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $112 total per night from Apr 20 to Apr 21
$112 total
Apr 20 - Apr 21
Total with taxes and fees
8.4/10 Very Good! (2,556 reviews)
The room was great front desk staff was amazing. Mercedes was delightful and very professional

Reviewed on Apr 7, 2026

Royal Regency Hotel
See all 584 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 $676, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.