New Windsor Vacations from $302

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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.
citizenM Washington DC NoMa

citizenM Washington DC NoMa

4 out of 5
Northeast
Price was $492, price is now $302 per person
$302
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (2,975 reviews)
No parking on site, it was a bit of a hassle and expensive

Reviewed on Oct 27, 2026

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 $973, price is now $530 per person
$530
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,265 reviews)
NA

Reviewed on Oct 27, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was $1,062, price is now $598 per person
$598
per person
Dec 24 - Dec 28
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.6/10 Exceptional! (133 reviews)
tiny tiny room with no closet- not sure what the “resort fee” was for- but it was in town and by a trail so that was nice. Was definitely not worth what we paid- but they get you with convenience i guess… very clean room.

Reviewed on Oct 16, 2026

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
Price was $724, price is now $418 per person
$418
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,007 reviews)

citizenM Washington DC Georgetown

citizenM Washington DC Georgetown

4 out of 5
Northwest
Price was $536, price is now $341 per person
$341
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (186 reviews)

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Stay near popular New Windsor attractions

Old Westminster Winery

6.8/10 (11 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.
See properties

New Windsor Hotel Deals

Sunday Morning at Savannahs

Sunday Morning at Savannahs

4 out of 5
111 South Springdale Avenue, New Windsor New Windsor MD
$231 nightly
The price is $247 total per night from Oct 29 to Oct 30
$247 total
Oct 29 - Oct 30
Total with taxes and fees
10/10 Exceptional! (2 reviews)
"We had a girls night here. Everything was excellent. It was a beautiful facility. It has lots of charming character. You feel like you have simply left home and went to stay at your grandmother's house, which is a very good thing In my book I felt right at home. When we arrived there were snacks ..."

Reviewed on Oct 26, 2026

Sunday Morning at Savannahs
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
$136 nightly
The price is $154 total per night from Nov 9 to Nov 10
$154 total
Nov 9 - Nov 10
Total with taxes and fees
Turf Valley Resort
Inn at Cemetery Hill

Inn at Cemetery Hill

2 out of 5
613 Baltimore St Gettysburg PA
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $111 total per night from Nov 24 to Nov 25
$111 total
Nov 24 - Nov 25
Total with taxes and fees
Inn at Cemetery Hill
See all 350 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 $302 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.