Westchester Vacations

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Find the Best Westchester Vacation Packages

Westchester Hotel Deals

Hyatt Regency Dulles International Airport

Hyatt Regency Dulles International Airport

4 out of 5
2300 Dulles Corner Blvd Herndon VA
Fully refundableReserve now, pay when you stay
The price is ￥19,927 per night from Jul 24 to Jul 25
￥19,927
￥22,916 total
Jul 24 - Jul 25
includes taxes & fees
8.8/10 Excellent! (1,837 reviews)
"The building's air conditioning system was out of service due to damage, yet we were not informed of this serious issue before or during check-in. We stayed in a corner room on the top floor on July 3 and 4, and the lack of air conditioning made the room extremely hot and uncomfortable. Had we been ..."

Reviewed on Jul 10, 2026

Hyatt Regency Dulles International Airport
Courtyard by Marriott Springfield

Courtyard by Marriott Springfield

3 out of 5
6710 Commerce St Springfield VA
Fully refundableReserve now, pay when you stay
The price is ￥17,979 per night from Jul 19 to Jul 20
￥17,979
￥20,678 total
Jul 19 - Jul 20
includes taxes & fees
8.4/10 Very Good! (1,033 reviews)
"Staff was very nice and attentive"

Reviewed on Jul 9, 2026

Courtyard by Marriott Springfield
Hilton Fairfax

Hilton Fairfax

3.5 out of 5
12777 Fair Lakes Cir Fairfax VA
Fully refundableReserve now, pay when you stay
The price is ￥19,754 per night from Aug 7 to Aug 8
￥19,754
￥22,717 total
Aug 7 - Aug 8
includes taxes & fees
9/10 Wonderful! (1,081 reviews)
"Normally I would rate my stay higher. The hotel is wonderfully situated right of Route 66 and the rooms have been renovated and offer a pleasant stay. Unfortunately most of their elevators were not working which made for a frustrating stay. I had to actually call down the morning find my checkout ..."

Reviewed on Jul 10, 2026

Hilton Fairfax
See all 722 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.

What to do in Westchester

Sushi Masterclass in Washington D.C.

Sushi Masterclass in Washington D.C. (Includes 4-Course Meal)

￥20,318
per adult
Sushi Masterclass in Washington D.C. (Includes 4-Course Meal)
See all activities in Westchester

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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.