New Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
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

SIXTY DC

2 out of 5
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

Salamander Washington DC

5 out of 5
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

The Churchill Hotel near Embassy Row

4 out of 5
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

Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
Northwest
Price was CA $1,002, price is now CA $686 per person
CA $686
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
8.8/10 Excellent! (2,052 reviews)
The hotel was great!

Reviewed on Aug. 21, 2025

Ready to book your vacation to New Windsor?

 

Choose your dates

New Windsor Hotel Deals

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 $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

Country Inn & Suites by Radisson, Frederick, MD
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 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

Hyatt Place Baltimore/Owings Mills
Hilton Garden Inn Frederick

Hilton Garden Inn Frederick

3 out of 5
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

Hilton Garden Inn Frederick
See all 312 properties in New Windsor
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a New Windsor vacation package cost?
You can pick up a vacation package to this top destination from CA $491 on Expedia. But how much your vacation to New Windsor costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to New Windsor?
If you'd like to snag a cheap New Windsor vacation package, consider travelling in January, February and April. You'll usually find better prices on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for New Windsor?
Usually, a handful of days is enough to check out the top attractions during your New Windsor vacation. However, if you want to have more time to relax or go on day tours, consider extending your trip.
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 some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect New Windsor package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your New Windsor getaway 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 escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to New Windsor?
If you've got your New Windsor vacation dates finalized, book as early as you can to bag some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to New Windsor?

  1. Choose your travel dates: The things you want to do in New Windsor and your preferred season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will probably be the biggest expense during your trip to New Windsor.
  3. Decide your trip length: Think about how much time you want to spend discovering New Windsor. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a New Windsor vacation package that brings all your bookings together.

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