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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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
per person
Oct 1 - Oct 4
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,000 reviews)
Wish there was coffee in the lobby at all times

Reviewed on Jul. 8, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
per person
Sep 27 - Sep 30
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,001 reviews)
The staff was very nice and attentive to issues, but overall the property was a bit run down, smaller for what you pay for, dog barking constantly next door, TV didn't work, and Rollaway wasn't in room as requested. The price is truly for location and history, but truly don't think worth the price when extras that would normally be included in the price of the hotel, you had to pay extra.

Reviewed on Jul. 13, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Oct 1 - Oct 4
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
10/10 Exceptional! (3 reviews)
It’s a nice facility. The room was clean and spacious. Bathroom was well appointed. They have a nice cocktail bar and a restaurant. I did not have dinner there, I did have a couple of cocktails and some apps in the cocktail bar. Definitely recommend making time to stop there.

Reviewed on Jul. 13, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
The property was beautiful and has an opportunity to eat at Dogon restaurant! Excellent food!

Reviewed on Jul. 11, 2025

Courtyard Silver Spring Downtown

Courtyard Silver Spring Downtown

3 out of 5
Downtown Silver Spring
Save 100% on your flight
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.8/10 Excellent! (1,000 reviews)
A good place to stay. But bring your own pillows, water, and food

Reviewed on Jul. 13, 2025

Ready to book your vacation to New Windsor?

 

Choose your dates

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 $127 per night from Jul 15 to Jul 16
CA $127
CA $147 total
Jul 15 - Jul 16
includes taxes & fees
8/10 Very Good! (1,035 reviews)
"I will stay again."

Reviewed on Jul. 13, 2025

Hyatt Place Baltimore/Owings Mills
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 $113 per night from Aug 6 to Aug 7
CA $113
CA $126 total
Aug 6 - Aug 7
includes taxes & fees
8.2/10 Very Good! (1,053 reviews)
"Fast check in. Comfortable bed."

Reviewed on Jul. 13, 2025

Country Inn & Suites by Radisson, Frederick, MD
Turf Valley Resort
Turf Valley Resort
3.5 out of 5
2700 Turf Valley Rd, Ellicott City, MD
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Jul 17 to Jul 18
CA $178
CA $202 total
Jul 17 - Jul 18
includes taxes & fees
8.6/10 Excellent! (904 reviews)
"We have stayed before and found that it is an excellent resort."

Reviewed on Jul. 10, 2025

Turf Valley Resort
See all 310 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 $721 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.