New Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
Northwest
Price was CA $1,003, price is now CA $731 per person
CA $731
per person
Sep 3 - Sep 7
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (2,188 reviews)
Nice little hotel near Union Station with good prices and nice staff. Restaurant is the Dubliner pub with great food
Reviewed on Jun 8, 2026
Kellogg Conference Hotel at Gallaudet University
Northeast
Price was CA $1,005, price is now CA $744 per person
CA $744
per person
Jul 15 - Jul 19
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very Good! (1,008 reviews)
Be sure to ask about the pass to get out to Union Market...you can't get out that way without the pass....which unhelpfully they don't mention.
Reviewed on Jun 5, 2026
The Churchill Hotel near Embassy Row
Northwest
Price was CA $925, price is now CA $705 per person
CA $705
per person
Jul 15 - Jul 19
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,011 reviews)
The staff was very kind sand accommodating. We arrived early and they worked hard to find us a room that was ready.
Reviewed on Jun 7, 2026
Club Quarters Hotel in Washington DC
Downtown Washington D.C.
Price was CA $939, price is now CA $733 per person
CA $733
per person
Jul 21 - Jul 24
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,892 reviews)
The noise level is outrageous. 2 nights in a high floor and I could hear everything outside the window down below. I have never stayed in a hotel that wasn’t sound proof when it comes to the windows. As a light sleeper I do not recommend. But if you can sleep through anything . It’s decent and right next to the metro train for easy access to everything.
Reviewed on Jun 8, 2026
New Windsor Hotel Deals
Inn at Cemetery Hill
613 Baltimore St Gettysburg PA
The price is CA $204 per night from Jun 11 to Jun 12
CA $204
CA $226 total
Jun 11 - Jun 12
includes taxes & fees
9.4/10 Exceptional! (1,037 reviews)
"Good breakfast, plenty of choices"
Reviewed on Jun 8, 2026
Country Inn & Suites by Radisson, Frederick, MD
5579 Spectrum Dr Frederick MD
Fully refundable
The price is CA $130 per night from Jul 2 to Jul 3
CA $130
CA $145 total
Jul 2 - Jul 3
includes taxes & fees
8.2/10 Very Good! (1,323 reviews)
"I have stay at The Country Inn and Suites in Frederick a number of times and have been happy with each stay. I had requested an accessible room and got it. The room was pleasant with sufficient lighting. Tho it would be nice to have a night lite in the bathroom. But this is a failing of many hotels. ..."
Reviewed on Jun 8, 2026
Hyatt Place Baltimore/Owings Mills
4730 Painters Mill Rd Owings Mills MD
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Jun 16 to Jun 17
CA $137
CA $158 total
Jun 16 - Jun 17
includes taxes & fees
8.2/10 Very Good! (1,286 reviews)
"The room had not been clean hair as every where from the shower on linens. Dust on bed and nightstand. Bed was comfortable however I brought my own bed lined and bath towels. For a Hyatt property I expected more. This was the my worst experience with a Hyatt property"
Reviewed on Jun 8, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
