New Windsor Vacations from $419

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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.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
per person
Sep 11 - Sep 14
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9/10 Wonderful! (1,791 reviews)
Very nice. Located in heart of Annapolis. Everything is walkable, harbor, naval academy, state house, restaurants and ships. Would stay here again.

Reviewed on Jun 30, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
10/10 Exceptional! (3 reviews)
Very difficult to pull up and take advantage of valet parking. Otherwise, everything was AMAZING!

Reviewed on Jun 29, 2025

La Quinta Inn & Suites by Wyndham Washington DC / NoMa

La Quinta Inn & Suites by Wyndham Washington DC / NoMa

3 out of 5
Northeast
Save 100% on your flight
per person
Sep 22 - Sep 27
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
7.8/10 Good! (123 reviews)
Nothing positive or negative to say

Reviewed on Jun 29, 2025

Pendry Washington DC - The Wharf

Pendry Washington DC - The Wharf

5 out of 5
Southwest
Save 100% on your flight
per person
Sep 18 - Sep 24
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (296 reviews)
The view was beautiful, but the room was small and definitely not worth $4,500.

Reviewed on Jun 28, 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Save 100% on your flight
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,477 reviews)
Clean and convenient

Reviewed on Jun 24, 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
$120 nightly
The price is $139 total per night from Jul 2 to Jul 3
$139 total
Jul 2 - Jul 3
Total includes taxes and fees
8.2/10 Very Good! (1,007 reviews)
"Me and my family truly enjoyed our stay . the staff was inviting and very helpful. the Room attendants helped me keep towels and trash bags stocked since my family would sleep really late. there's plenty of shopping very close by and lots of restaurants to choose from close by . this was our 2nd ..."

Reviewed on Jun 26, 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
$80 nightly
The price is $88 total per night from Jul 7 to Jul 8
$88 total
Jul 7 - Jul 8
Total includes taxes and fees
8.2/10 Very Good! (1,028 reviews)
Highly recommended
"I would highly recommend this hotel. It was a great stay."

Reviewed on Jun 25, 2025

Country Inn & Suites by Radisson, Frederick, MD
Holiday Inn Express and Suites Gettysburg by IHG
Holiday Inn Express and Suites Gettysburg by IHG
2.5 out of 5
1871 Gettysburg Village Drive, Gettysburg, PA
Fully refundable
$156 nightly
The price is $173 total per night from Jul 6 to Jul 7
$173 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (1,008 reviews)
"All good."

Reviewed on Jun 26, 2025

Holiday Inn Express and Suites Gettysburg by IHG
See all 302 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 $419 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.