
New Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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Better together
Save up to CA $1,096 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.

Hotel Arboretum
Northeast
Price was CA $758, price is now CA $491 per person
CA $491
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
8/10 Very Good! (968 reviews)
People camping on the medium strip between highways. Stranger in front of hotel door cornered me and talked for over 30 minutes when all I wanted to do is get in my room and chill.
Reviewed on Aug. 18, 2025

SIXTY DC
Downtown Washington D.C.
Price was CA $1,321, price is now CA $795 per person
CA $795
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
9.8/10 Exceptional! (28 reviews)
Accommodating staff,professional,pleasant. Clean,I’d stay again!
Reviewed on Aug. 20, 2025

Salamander Washington DC
Southwest
Price was CA $2,143, price is now CA $1,301 per person
CA $1,301
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
9.4/10 Exceptional! (1,002 reviews)
This hotel was beautiful, spotless, exceptional staff and the food was delicious. We will only stay here when we're back in DC.
Reviewed on Aug. 20, 2025

The Churchill Hotel near Embassy Row
Northwest
Price was CA $1,057, price is now CA $690 per person
CA $690
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
8.8/10 Excellent! (1,821 reviews)
I really enjoyed staying at a smaller hotel with charm! The staff is so nice and the location is great. Would stay here again.
Reviewed on Aug. 16, 2025
New Windsor Hotel Deals

Country Inn & Suites by Radisson, Frederick, MD
5579 Spectrum Dr, Frederick, MD
Fully refundable
The price is CA $119 per night from Aug 27 to Aug 28
CA $119
CA $132 total
Aug 27 - Aug 28
includes taxes & fees
8.2/10 Very Good! (1,088 reviews)
"Front desk staff were welcoming & friendly. Many dining options nearby. Convenient location. Room was clean. Breakfast was typical-waffles eggs sausage potatoes pastrues yogurt etc Coffee available throughout the stay. Beds wete comfortable with ample pillows and extra blankets. Overall a nice ..."
Reviewed on Aug. 16, 2025

Hyatt Place Baltimore/Owings Mills
4730 Painters Mill Rd, Owings Mills, MD
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Sep 7 to Sep 8
CA $139
CA $160 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very Good! (1,096 reviews)
"Convenient"
Reviewed on Aug. 19, 2025

Hilton Garden Inn Frederick
7226 Corporate Ct, Frederick, MD
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 31 to Sep 1
CA $151
CA $168 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
Good
"Friendly staff, clean, bathroom just needs updating."
Reviewed on Aug. 18, 2025
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.
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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.