Westchester Vacations from $265

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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.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Price was $599, price is now $265 per person
$265
per person
Apr 11 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
Everything was excellent!

Reviewed on Jan 25, 2026

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Price was $1,254, price is now $269 per person
$269
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (2,262 reviews)
The staff was very friendly and helpful!

Reviewed on Feb 1, 2026

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $658, price is now $412 per person
$412
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (1,002 reviews)
Rooms were very clean and staff was pleasant

Reviewed on Jan 22, 2026

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Price was $508, price is now $329 per person
$329
per person
Apr 11 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,002 reviews)
Room was nice and the bathroom was spacious with lots of room for your personal items. Check-in was full. And the staff was friendly

Reviewed on Feb 2, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $972, price is now $650 per person
$650
per person
Apr 24 - Apr 27
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.6/10 Excellent! (1,008 reviews)
Clean room, staff very polite and gentle

Reviewed on Jan 19, 2026

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Discover the most popular places to visit in Westchester

Visitor Center on the Manassas National Battlefield Park, Virginia, USA

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 acclaimed theater scene and shops in this family-friendly area.

Historic Manassas Visitor Center
Water park with colorful slides and pools

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
American flags in front of the Manasas Museum, Old Town Manassas, Virginia, USA

Manassas Museum

You can spend time browsing the exhibits at Manassas Museum during your travels in Manassas. Experience the lively festivals and great live music in this family-friendly area.

Manassas Museum

Westchester Hotel Deals

Wingate by Wyndham Springfield

Wingate by Wyndham Springfield

2.5 out of 5
6550 Loisdale Court Springfield VA
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $102 total per night from Feb 9 to Feb 10
$102 total
Feb 9 - Feb 10
Total with taxes and fees
8.2/10 Very Good! (1,406 reviews)
Nice clean room and the most comfortable bed I've ever been in .

Reviewed on Jan 27, 2026

Wingate by Wyndham Springfield
Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd Herndon VA
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $111 total per night from Feb 6 to Feb 7
$111 total
Feb 6 - Feb 7
Total with taxes and fees
8.8/10 Excellent! (1,576 reviews)
Great

Reviewed on Jan 28, 2026

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
$101 nightly
The price is $116 total per night from Feb 9 to Feb 10
$116 total
Feb 9 - Feb 10
Total with taxes and fees
8.2/10 Very Good! (2,702 reviews)
Clean, quiet and spacious.

Reviewed on Jan 28, 2026

Hyatt Place Herndon Dulles Airport East
See all 728 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.

Find the Best Westchester Vacation Packages

Westchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Ronald Reagan Washington National Airport (DCA)
Top Sights
Splash Down Water Park, Historic Manassas Visitor Center and Manassas Museum

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Frequently asked questions

How much does a Westchester vacation package cost?
Offering great value package deals from $265 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.