
New Windsor Vacations from $156
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Your New Windsor Vacation
Food, history, entertainment and more … There's so much to discover with a New Windsor vacation package. And with the ability to customize your city getaway, it's guaranteed to be one you won't forget. Make sure to spend some time sightseeing during your trip to New Windsor. Old Westminster Winery and Elk Run Vineyards are some favorite places to check out. Whoever you're escaping with and whatever your bank balance, your dream New Windsor vacation is just a few clicks away with Expedia.
The Latest New Windsor vacation packages



DoubleTree by Hilton Hotel Laurel
Reviewed on Aug 24, 2025

InterContinental Washington D.C. - The Wharf by IHG
Reviewed on Aug 24, 2025

Club Quarters Hotel in Washington DC
Reviewed on Aug 25, 2025
Discover the most popular places to visit in New Windsor
Old Westminster Winery
You can enjoy a tasting or tour at Old Westminster Winery during your travels to New Windsor. While in this family-friendly area, you can enjoy the restaurants.
New Windsor Hotel Deals

Country Inn & Suites by Radisson, Frederick, MD
Reviewed on Aug 21, 2025

Hyatt Place Baltimore/Owings Mills
Reviewed on Aug 21, 2025

Hilton Garden Inn Frederick
Reviewed on Aug 24, 2025