Westchester Vacations from $308

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Your Westchester Vacation

Save time and energy on your travel planning with a Westchester vacation package. One of the best neighborhoods to base yourself in this amazing city is Wellington, which is good for culture and much more. You'll want to sightsee during your trip to Westchester. Don't miss major attractions such as Historic Manassas Visitor Center, Hylton Performing Arts Center and Manassas Museum. Don't delay exploring this destination any longer. Your dream Westchester vacation is only a few clicks away with Expedia.

The Latest Westchester vacation packages

Price found within the past 48 hours. Click for updated prices.
The Westin Tysons Corner

The Westin Tysons Corner

4 out of 5
Price was $381, price is now $308 per person
$308
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,006 reviews)
The front desk staff was phenomenal

Reviewed on Aug 30, 2025

Hilton McLean Tysons Corner

Hilton McLean Tysons Corner

4 out of 5
Save 100% on your flight
Price was $589, price is now $446 per person
$446
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,004 reviews)
I mostly love the clean room and the view is very interesting. I look forward to staying there next time.

Reviewed on Sep 1, 2025

Embassy Suites by Hilton Tysons Corner

Embassy Suites by Hilton Tysons Corner

3.5 out of 5
Save 100% on your flight
Price was $475, price is now $381 per person
$381
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (2,773 reviews)
The service is excelent

Reviewed on Sep 2, 2025

La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport

La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport

3 out of 5
Price was $478, price is now $394 per person
$394
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Washington (DCA)
8.6/10 Excellent! (860 reviews)
It was nice for the stay, could be cleaner around and under the beds. Other than that I’d say it was a pretty good stay

Reviewed on Aug 31, 2025

Tru by Hilton Manassas

Tru by Hilton Manassas

2.5 out of 5
Price was $583, price is now $491 per person
$491
per person
Nov 7 - Nov 10
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Washington (DCA)
9.4/10 Exceptional! (449 reviews)
Hotel was clean and well kept. Staff was friendly

Reviewed on Sep 2, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Westchester

Splash Down Water Park

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

Prince William Hospital

Though Prince William Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Manassas while you are here.

Prince William Hospital

Historic Manassas Visitor Center

Historic Manassas Visitor Center is just one of the places to see in Manassas, so why not enjoy the other things to explore during your travels? Discover the great live music and shops in this family-friendly area.

Historic Manassas Visitor Center

Westchester Hotel Deals

Best Western Fairfax

Best Western Fairfax

2.5 out of 5
3535 Chain Bridge Rd, Fairfax, VA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $98 total per night from Sep 5 to Sep 6
$98 total
Sep 5 - Sep 6
Total with taxes and fees
Best Western Fairfax
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
$101 nightly
The price is $116 total per night from Oct 3 to Oct 4
$116 total
Oct 3 - Oct 4
Total with taxes and fees
Hyatt Place Herndon Dulles Airport East
Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundable
$119 nightly
The price is $137 total per night from Sep 19 to Sep 20
$137 total
Sep 19 - Sep 20
Total with taxes and fees
Hyatt Regency Dulles
See all 643 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.

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Frequently asked questions

How much does a Westchester vacation package cost?
Offering great value package deals from $308 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?
You're likely to find reduced prices and better availability in December, January and February. Check out our cheap Westchester vacation packages and you could score some great off-season deals.
How many days is enough for Westchester?
The ideal length for your Westchester vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to go to all the leading sights and explore some hidden treasures along the way.
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.
Does Expedia offer Book Now, Pay Later Westchester vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Westchester break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.