New Windsor Vacations from $194

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest New Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $332, price is now $194 per person
$194
per person
Nov 11 - Nov 14
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,015 reviews)
Staff was excellent

Reviewed on Oct 10, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $885, price is now $431 per person
$431
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.8/10 Exceptional! (55 reviews)
The room was small and limited in space to move around. Staff were easy to talk to and receive support. Overall, the location provided many options for walking to historic locations or to take a short uber drive to the Capital, White House or many other areas of interest.

Reviewed on Oct 10, 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
Price was $453, price is now $257 per person
$257
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
Bed was super comfy. Restaurant was good. Friendly staff. Clean.

Reviewed on Oct 10, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was $596, price is now $345 per person
$345
per person
Dec 28 - Dec 31
found 15 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,010 reviews)
Parking is expensive and the pool wasn’t actually heated.

Reviewed on Oct 11, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $626, price is now $382 per person
$382
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,002 reviews)
Bathroom was outdated and bathtub was poorly kept. Staff was pleasant overall and the property itself was decent.

Reviewed on Oct 10, 2025

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Discover the most popular places to visit in New Windsor

Old Westminster Winery

4/5(2 reviews)

You can enjoy a tasting or tour at Old Westminster Winery during your travels to New Windsor. While in this family-friendly area, you can enjoy the restaurants.

Old Westminster Winery

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
$93 nightly
The price is $107 total per night from Nov 2 to Nov 3
$107 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (1,139 reviews)
"The staff was very friendly and kind."

Reviewed on Oct 8, 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
$87 nightly
The price is $96 total per night from Nov 4 to Nov 5
$96 total
Nov 4 - Nov 5
Total with taxes and fees
8.2/10 Very Good! (1,146 reviews)
"Not what I would have expected from a Radisson property."

Reviewed on Oct 11, 2025

Country Inn & Suites by Radisson, Frederick, MD
Eisenhower Hotel & Conference Center

Eisenhower Hotel & Conference Center

3 out of 5
2634 Emmitsburg Road, Gettysburg, PA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $110 total per night from Nov 10 to Nov 11
$110 total
Nov 10 - Nov 11
Total with taxes and fees
6.6/10 (1,005 reviews)
"Awesome time"

Reviewed on Oct 6, 2025

Eisenhower Hotel & Conference Center
See all 332 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.

New Windsor Essential Information

Language
English
Currency
U.S dollars
Population
1,400
Max Temp Winter
40ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a New Windsor vacation package cost?
You can snap up a vacation package to this destination from $194 on Expedia. However, how much your vacation to New Windsor costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to New Windsor?
If you'd like to snag a cheap New Windsor vacation package, consider visiting in January, September and December. You'll generally find lower prices on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for New Windsor?
With a well-organized schedule, you can easily hit the main New Windsor attractions in a handful of days. But if you prefer to discover hidden gems or take day trips, think about booking your New Windsor vacation for longer.
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 a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect New Windsor package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your New Windsor adventure 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 retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to New Windsor?
Enjoy fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment New Windsor trip.
Does Expedia offer Book Now, Pay Later New Windsor vacation packages?
Jet off on your perfect trip to New Windsor with Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until your next paycheck — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stay on budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.