Westchester County Vacations & Trips from $495

For a weekend trip, Elmsford typically offers the lowest prices for a Westchester County vacation package, while White Plains has the highest, and Elmsford also features the lowest upper price range.


*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

When you bundle, you can save up to 30%*. To save money on a Westchester County package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

A Westchester County vacation package lets you combine flights, hotel stays, and rental cars, based in one of the region's top destinations. In Yonkers, most hotels offer airport shuttle service to and from New York, NY (JFK-John F. Kennedy Intl.) and include free breakfast. In Tarrytown, most hotels also provide airport shuttle service and free breakfast. For White Plains, nearly all hotels offer airport shuttle service to and from White Plains, NY (HPN-Westchester County) and include free breakfast.


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

New Rochelle, Elmsford, Yonkers, and Dobbs Ferry are some of the top destinations for cheap Westchester County vacation package deals. For an affordable weekend getaway, New Rochelle is often among the most budget-friendly options, with package prices starting around $390 per adult. For notable bundle savings, Dobbs Ferry is often among the best options, with flight-and-hotel bundles saving around $120 per adult.


Browse cheap vacation packages in Westchester County on Expedia to compare current deals.


*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

The best time for a Westchester County vacation package depends on which destination you choose.


Yonkers is busiest in December, when highs are around 43°F, and in September, with highs around 76°F, coinciding with the Yonkers Riverfest. For fewer crowds, consider November, when highs are around 52°F, or March, with highs around 48°F.


White Plains sees most demand in July, with highs around 83°F, and September, when highs are around 74°F. If you prefer a quieter visit, January, with highs around 36°F, or October, with highs around 63°F, see fewer visitors.


Tarrytown is most popular in October, when highs are around 64°F, and September, with highs around 76°F, which includes the Sleepy Hollow Street Fair. For a more tranquil trip, January, with highs around 36°F, and February, with highs around 39°F, are quieter.


New Rochelle sees its peak bookings in July, with highs around 84°F, and December, when highs are around 43°F. For a less busy experience, October, with highs around 64°F, or February, with highs around 40°F, are quieter.

Westchester County vacation packages offer a variety of styles across its popular cities like Yonkers, Tarrytown, White Plains, Elmsford, and New Rochelle:

• Budget: In Yonkers, Hilltop Inn & Suites provides a comfortable stay with free breakfast and free WiFi, making it a solid choice for value-focused travelers.
• Couples: Tarrytown offers the 3.5-star Sleepy Hollow Hotel, a Dolce by Wyndham, which features a spa and indoor pool, with travelers often praising the amazing staff and excellent food.
• Family: The Opus Westchester, Autograph Collection in White Plains, a 5-star property rated 8.3 out of 10 by travelers, includes family rooms and an indoor pool, and travelers frequently highlight its super clean overall experience and great staff.
• Pet-friendly: For those traveling with pets, Days Inn by Wyndham Elmsford / White Plains in Elmsford offers pet-friendly accommodations and free breakfast, with travelers often noting the nice rooms and great breakfast.
• Beach: In New Rochelle, Hotel NoMa, Trademark Collection by Wyndham, rated 8.2 out of 10 by travelers, features an outdoor pool and is about 1 mile from Glen Island Park, providing access to water activities; travelers liked the great food and good breakfast.

For a Westchester County vacation, consider these destinations based on your travel style:

• Yonkers: A popular package base for those seeking urban attractions and family-friendly activities, with a good range of lodging choices.
• Tarrytown: Ideal for travelers interested in historic sites and outdoor activities, offering a charming base for exploring the region.
• White Plains: A central hub well-suited for business travelers and those looking for entertainment options within a vibrant city setting.
• Elmsford: Offers a more relaxed atmosphere with cultural attractions and convenient lodging, making it a good choice for a quieter stay.

A Westchester County vacation is primarily suited for cultural trips and urban exploration, with a strong focus on family-friendly attractions and outdoor activities.


The region offers a rich array of historic sites, such as Philipse Manor Hall in Yonkers and Lyndhurst in Tarrytown, alongside various city and urban attractions, and some areas provide waterfront access.


Travelers planning a Westchester County vacation package will find it ideal for exploring history, enjoying city amenities, and engaging in outdoor pursuits.

For a Westchester County vacation, travelers can fly into several major airports. John F. Kennedy International Airport (JFK) and LaGuardia Airport (LGA) in New York City, along with Newark Liberty International Airport (EWR) in New Jersey, serve as primary gateways to the wider New York metropolitan area. For direct access within the county, Westchester County Airport (HPN) in White Plains offers a convenient option.

A Westchester County vacation offers diverse attractions across its many towns and cities:


Browse and book things to do in Westchester County on Expedia.

Yes, family vacation packages in Westchester County offer several hotels with kid-friendly amenities across its cities:


Your Westchester County vacation package can be customized around these family-friendly options.

For a Westchester County vacation package, booking around 2 to 5 weeks ahead is a useful window, though the timing varies slightly across its main destinations.


Travelers tend to book trips to these destinations most often in February, from July to December. If you're planning a spontaneous getaway, Expedia also offers last-minute Westchester County vacation packages.

Most Westchester County vacation packages last around 3 days, but the ideal trip length depends on where you're going and what you'd like to experience.


Yonkers, a city known for its urban attractions and family-friendly appeal, is well suited for a trip of around 3 days. Weekend trips are most popular, though week-long stays are also common, allowing time to catch a game at Yankee Stadium.


Tarrytown, a charming area with family-friendly attractions and outdoor activities, also typically sees trips of around 3 days. Weekend trips are most popular, and week-long stays are also chosen by many, giving you time to explore the historic Lyndhurst Mansion.


White Plains, a central urban destination offering entertainment and family-friendly attractions, is also often visited for around 3 days. Weekend trips are most popular, with some travelers also opting for week-long stays, perfect for shopping at The Westchester Mall.

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Westchester County vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

To find last-minute vacation packages to Westchester County, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Free cancellation on a Westchester County vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Westchester County getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.