New Windsor Vacations from $370
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The Latest New Windsor Vacation Packages
- Eurostars Saint Gregory Dupont Circle Georgetown
Sep 27 - Sep 30Eurostars Saint Gregory Dupont Circle Georgetown + Flight
Downtown Washington D.C.3 nights4.0 star property8.8/10 - Excellent (1,007 reviews)"Très bien , et bien situé … pas trop cher pour l’emplacement"Reviewed July 21, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - Hotel Burg
Oct 2 - Oct 5Hotel Burg + Flight
Leesburg's Old and Historic District3 nights4.0 star property9.6/10 - Exceptional (97 reviews)"Staff went out of their way to help in any way they could."Reviewed July 19, 2026Roundtrip • Boston (BOS) - Baltimore (BWI)BOS - BWI • Nonstop BWI - BOS • Nonstop - The Churchill Hotel near Embassy Row
Sep 27 - Sep 30The Churchill Hotel near Embassy Row + Flight
Northwest3 nights4.0 star property8.8/10 - Excellent (1,013 reviews)"Very helpful, friendly staff. Nice, smaller property that did not have the crush of people."Reviewed July 22, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - Crowne Plaza Crystal City-Washington, D.C. by IHG
Oct 7 - Oct 11Crowne Plaza Crystal City-Washington, D.C. by IHG + Flight
Crystal City4 nights3.5 star property8.4/10 - Very Good (1,001 reviews)Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - Phoenix Park Hotel
Oct 4 - Oct 7Phoenix Park Hotel + Flight
Northwest3 nights3.5 star property9.4/10 - Exceptional (2,174 reviews)"Smaller room and elevator, but well maintained and clean. Staff was very friendly. I appreciated the free beverage at The Dubliner."Reviewed July 22, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop
New Windsor Hotel Deals
Best Western Westminster Hotel
Best Western Westminster Hotel
Days Inn by Wyndham Westminster
Days Inn by Wyndham Westminster
Hampton Inn & Suites Frederick-Fort Detrick
Hampton Inn & Suites Frederick-Fort Detrick
SpringHill Suites by Marriott Frederick
SpringHill Suites by Marriott Frederick
Holiday Inn Express and Suites Gettysburg by IHG
Holiday Inn Express and Suites Gettysburg by IHG
City Express By Marriott Gettysburg
City Express By Marriott GettysburgFrequently Asked Questions
How much does a New Windsor vacation package cost?
You can snap up a vacation package to this destination from $370 on Expedia. However, how much your vacation to New Windsor costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to New Windsor?
If you'd like to snag a cheap New Windsor vacation package, consider visiting in January, September and December. You'll generally find lower prices on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for New Windsor?
With a well-organized schedule, you can easily hit the main New Windsor attractions in a handful of days. But if you prefer to discover hidden gems or take day trips, think about booking your New Windsor vacation for longer.
How to find the best New Windsor package deals?
Begin your search for a New Windsor package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect New Windsor package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your New Windsor adventure off to a flying start.
Is it cheaper to book a New Windsor vacation as a package?
You can enjoy significant savings on your New Windsor retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to New Windsor?
Enjoy fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment New Windsor trip.
Does Expedia offer Book Now, Pay Later New Windsor vacation packages?
Jet off on your perfect trip to New Windsor with Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until your next paycheck — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stay on budget and snag great deals while they last.