New Windsor Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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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.

Top New Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Phoenix Park Hotel
Sofitel Washington DC Lafayette Square
Kellogg Conference Hotel at Gallaudet University
Club Quarters Hotel in Washington DC
Tysons Corner Marriott

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New Windsor Hotel Deals

Hyatt Place Baltimore/Owings Mills

Hyatt Place Baltimore/Owings Mills

3 out of 5
4730 Painters Mill Rd Owings Mills MD
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Jul 26 to Jul 27
CA $139
CA $161 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very good! (1,304 reviews)
"Great place"

Reviewed on Jun 25, 2026

Hyatt Place Baltimore/Owings Mills
Inn at Cemetery Hill

Inn at Cemetery Hill

2 out of 5
613 Baltimore St Gettysburg PA
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jul 26 to Jul 27
CA $190
CA $210 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"Great location, clean hotel and very comfortable bed. I would definitely stay here again. Friendly staff also. Shout out to Karen for helping us with a minor problem. She was wonderful."

Reviewed on Jun 26, 2026

Inn at Cemetery Hill
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr Frederick MD
Fully refundable
The price is CA $144 per night from Jul 5 to Jul 6
CA $144
CA $160 total
Jul 5 - Jul 6
includes taxes & fees
8.2/10 Very good! (1,331 reviews)
"All was good except if you boom via other platforms this hotel isn’t great with accommodations."

Reviewed on Jun 24, 2026

Country Inn & Suites by Radisson, Frederick, MD
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.

Stay near popular New Windsor attractions

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.