New Windsor Vacations from $136

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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.

The Latest New Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

4 out of 5
Mount Vernon
Save 100% on your flight
Price was $259, price is now $136 per person
$136
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (979 reviews)
I love a good unique stay which is what Ulysses was but it lacked some basic accommodations.. also the parking is super weird and it's crazy that they don't offer valet parking .. I also think it's weird that your not able to control the heat and or air individually in your room

Reviewed on Nov 29, 2025

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was $1,485, price is now $671 per person
$671
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip flight included
Miami (MIA) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
The staff especially Marcus & Noam, the valet. I hope I spelled that correctly.

Reviewed on Nov 20, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was $545, price is now $256 per person
$256
per person
Jan 8 - Jan 11
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
Dining room upgrade and staff are excellent

Reviewed on Nov 30, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $821, price is now $412 per person
$412
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,084 reviews)
Great hotel in an excellent location that is close to most museums

Reviewed on Nov 27, 2025

SIXTY DC

SIXTY DC

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,058, price is now $571 per person
$571
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip flight included
Miami (MIA) to Washington (DCA)
9.4/10 Exceptional! (76 reviews)
Clean, smart and comfortable

Reviewed on Nov 30, 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
$84 nightly
The price is $97 total per night from Dec 21 to Dec 22
$97 total
Dec 21 - Dec 22
Total with taxes and fees
8.2/10 Very Good! (1,195 reviews)
Beautiful hotel and room. Nice breakfast selections.

Reviewed on Nov 25, 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
$88 nightly
The price is $97 total per night from Dec 21 to Dec 22
$97 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (1,013 reviews)
Very loud with kids running amok

Reviewed on Nov 25, 2025

Hilton Garden Inn Frederick
Marriott Owings Mills Metro Centre

Marriott Owings Mills Metro Centre

4 out of 5
10101 Grand Central Avenue Owings Mills MD
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $153 total per night from Dec 8 to Dec 9
$153 total
Dec 8 - Dec 9
Total with taxes and fees
9.2/10 Wonderful! (443 reviews)
Everything was great, the room was exactly like the pictures, but even better in person. Very clean & friendly staff, i felt valued, i definitely will be coming back.

Reviewed on Nov 24, 2025

Marriott Owings Mills Metro Centre
See all 331 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.

Find the Best New Windsor Vacation Packages

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 $136 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.