New Windsor Vacations from $378

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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.
Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Save 100% on your flight
Price was $574, price is now $378 per person
$378
per person
Jul 24 - Jul 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,001 reviews)
It’s very clean and in great area close to the shopping mall

Reviewed on May 13, 2026

The Bethesdan Hotel, Tapestry Collection by Hilton

The Bethesdan Hotel, Tapestry Collection by Hilton

4 out of 5
Bethesda Downtown
Save 100% on your flight
Price was $1,342, price is now $883 per person
$883
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,828 reviews)
Si quieres conocer Washington DC y quieres un hotel excelente calidad-precio, este es perfecto!. En si el hotel muy comodo (3.5- 4 estrellas), el cuarto excelente. Comodo y bien equipado. Abajo un bar, restaurante y su pequeña tienda. El sector súper tranquilo para caminar sin problemas. La calle de atrás hay full restaurantes, tiendas, etc. Alado del hotel hay un restaurante super bien ranqueado y un supermercado a media cuadra. El servicio al cliente bueno, nada del otro mundo. Ubicación: a 10 minutos caminando a la estación de tren y a 3 minutos en bus. La parada del bus es literalmente al pie. Desde la estación de metro hasta el centro de Washington son 30-35 min. En general, incluso al aeropuerto puedes moverte super bien en Metro sin necesidad de taxis o Uber. Relación costo/beneficio 100/100. Recomendado.

Reviewed on May 17, 2026

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
Price was $1,528, price is now $1,021 per person
$1,021
per person
Jul 19 - Jul 24
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,152 reviews)
Very well maintained property and friendly staff. I highly recommend to anyone wanting to stay in the area

Reviewed on May 18, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $715, price is now $484 per person
$484
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Unexpected upgrade at check in. Was much appreciated!

Reviewed on May 16, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $774, price is now $526 per person
$526
per person
Jul 11 - Jul 14
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Baltimore (BWI)
9.6/10 Exceptional! (67 reviews)
Everything was perfect, thank you!

Reviewed on May 15, 2026

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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

Inn at Cemetery Hill

Inn at Cemetery Hill

2 out of 5
613 Baltimore St Gettysburg PA
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $153 total per night from May 20 to May 21
$153 total
May 20 - May 21
Total with taxes and fees
9.4/10 Exceptional! (1,008 reviews)
"My stay was wonderful! Great place to stay."

Reviewed on May 18, 2026

Inn at Cemetery Hill
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
$97 nightly
The price is $108 total per night from Jun 14 to Jun 15
$108 total
Jun 14 - Jun 15
Total with taxes and fees
8.2/10 Very Good! (1,302 reviews)
"The staff was not friendly except at check in. Nobody would say "hello" when you entered the building. I have not seen this at other hotels."

Reviewed on May 17, 2026

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
$96 nightly
The price is $106 total per night from May 28 to May 29
$106 total
May 28 - May 29
Total with taxes and fees
6.8/10 (1,009 reviews)
"X"

Reviewed on May 18, 2026

Eisenhower Hotel & Conference Center
See all 345 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 $378 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.