Westchester Vacations

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Find the Best Westchester Vacation Packages

Westchester Hotel Deals

Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundableReserve now, pay when you stay
The price is ₩152,199 per night from Aug 15 to Aug 16
₩152,199
₩175,029 total
Aug 15 - Aug 16
includes taxes & fees
8.8/10 Excellent! (1,343 reviews)
A spa-like experience compared to Dulles
"A welcome reprieve from a 7-hour delay at Dulles. Staff was super friendly, room was very comfortable, and the food was excellent. Very grateful to have found this property!"

Reviewed on Jul 14, 2025

Hyatt Regency Dulles
Hyatt Place Herndon Dulles Airport East

Hyatt Place Herndon Dulles Airport East

3 out of 5
13711 Sayward Blvd, Herndon, VA
Fully refundableReserve now, pay when you stay
The price is ₩140,401 per night from Jul 27 to Jul 28
₩140,401
₩161,444 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (2,294 reviews)
"The room was spacious, convenient to food options, the parking was safe and easy, the hotel was quiet."

Reviewed on Jul 16, 2025

Hyatt Place Herndon Dulles Airport East
Best Western Fairfax

Best Western Fairfax

2.5 out of 5
3535 Chain Bridge Rd, Fairfax, VA
Fully refundableReserve now, pay when you stay
The price is ₩120,927 per night from Aug 15 to Aug 16
₩120,927
₩136,647 total
Aug 15 - Aug 16
includes taxes & fees
8/10 Very Good! (1,119 reviews)
"very good"

Reviewed on Jul 15, 2025

Best Western Fairfax
See all 628 properties in Westchester
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.

Discover the most popular places to visit in Westchester

Splash Down Water Park

4.5/5(2 reviews)

Enjoy the thrill rides with your kiddos at Splash Down Water Park as part of your trip to Sudley. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Splash Down Water Park

Hylton Performing Arts Center

5/5(1 review)

You can make plans for a show at Hylton Performing Arts Center during your stay in Manassas. Experience the area's great live music or attend a sporting event.

Hylton Performing Arts Center

Frequently asked questions

How much does a Westchester vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Westchester costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Westchester?
January, February and November are the best times to look for cheap Westchester vacation packages. Opting to travel in less busy periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Westchester?
With a well-planned schedule, you can easily tick off the most popular Westchester sights in a few days. But if you want to venture off the beaten track or go on day trips, consider booking your Westchester vacation for longer.
How to find the best Westchester package deals?
Finding a cheap Westchester package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Westchester package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Westchester vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging accommodations and flights individually. Better still, you can personalize your Westchester getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Westchester?
Land amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Westchester getaway.
How to plan a trip to Westchester?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred season and the type of activities available will also help you decide when to vacation in Westchester.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to set aside for your trip to Westchester. Then, pick a property that suits your budget, whether that's a low-cost stay or a more upscale getaway.
  3. Decide how long to go for: Now that you're up to speed on Westchester, you can work out the right length of your vacation. Create a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the right Westchester vacation package for you.