Westchester Vacations from $192
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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
- Holiday Inn Columbia East-Jessup by IHG
Jan 7 - Jan 11Holiday Inn Columbia East-Jessup by IHG + Flight
Jessup4 nights3.0 star property8.8/10 - Excellent (1,001 reviews)"Better than expected for the price. Very nice staff and clean. 1 or 2 questionable people outside during our 5 day stay, but nobody bothered us at all. I’d stay here again."Reviewed November 6, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop$307$192found 1 day agoper traveler - Sofitel Washington DC Lafayette Square
Jan 12 - Jan 17Sofitel Washington DC Lafayette Square + Flight
Downtown Washington D.C.5 nights5.0 star property9.0/10 - Wonderful (1,296 reviews)Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop$931$570found 1 day agoper traveler - citizenM Washington DC Capitol
Jan 20 - Jan 25citizenM Washington DC Capitol + Flight
Southwest5 nights4.0 star property9.0/10 - Wonderful (3,427 reviews)"Staff"Reviewed November 6, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - IAD • Nonstop BWI - ATL • Nonstop$554$352found 3 hours agoper traveler - Harbor free indoor parking
Jan 7 - Jan 11Harbor free indoor parking + Flight
Downtown Baltimore4 nights4.0 star propertyRoundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop$477$304found 1 day agoper traveler - Eurostars Saint Gregory Dupont Circle Georgetown
Jan 12 - Jan 17Eurostars Saint Gregory Dupont Circle Georgetown + Flight
Downtown Washington D.C.5 nights4.0 star property8.6/10 - Excellent (1,003 reviews)Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop$721$462found 1 day agoper traveler
Westchester Hotel Deals
La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport
La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport"Excellent hotel everything very clean The only problem is a noise that the bathroom vent makes; that's automatic, they leave it all day and turn it off until 10 p.m., then turn it on at 5 a.m. in the morning."
SpringHill by Marriott Centreville/Chantilly
SpringHill by Marriott Centreville/Chantilly"Clea well cared for and maintained. Good location"
Courtyard by Marriott Manassas Battlefield Park
Courtyard by Marriott Manassas Battlefield Park"Rundown hotel with poorly applied fresh paint and possibly new flooring. Bed was comfortable, it was quiet, and the WiFi was sufficient for video conferencing."
Frequently Asked Questions
How much does a Westchester vacation package cost?
Offering great value package deals from $192 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.