New Windsor Vacations from $156

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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 Arboretum

Hotel Arboretum

2 out of 5
Northeast
Price was $328, price is now $156 per person
$156
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8/10 Very Good! (1,007 reviews)
The Hotel Buffett was good. Most of the staff was friendly.

Reviewed on Aug 25, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was $968, price is now $488 per person
$488
per person
Nov 6 - Nov 11
found 18 hours ago
Roundtrip flight included
Miami (MIA) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful place! Amazing staff!

Reviewed on Aug 21, 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
Price was $388, price is now $222 per person
$222
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
Convenient external room door made it easy walking my dog. Did not have to walk thru.obby.

Reviewed on Aug 24, 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 $1,221, price is now $714 per person
$714
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.4/10 Exceptional! (1,000 reviews)
I love the area. Thenparking situation was awful. Hotel doesnt validate the parking where you could get a discount.

Reviewed on Aug 24, 2025

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $370, price is now $217 per person
$217
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.8/10 Excellent! (1,643 reviews)
Great location! The room itself was pretty clean,

Reviewed on Aug 25, 2025

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Discover the most popular places to visit in New Windsor

Old Westminster Winery

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

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
$90 nightly
The price is $100 total per night from Sep 3 to Sep 4
$100 total
Sep 3 - Sep 4
Total with taxes and fees
8.2/10 Very Good! (1,090 reviews)
"The hotel is quite and clean."

Reviewed on Aug 21, 2025

Country Inn & Suites by Radisson, Frederick, MD
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
$100 nightly
The price is $116 total per night from Sep 7 to Sep 8
$116 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (1,089 reviews)
Nice but needs more for money
"Had long wait to check in due to rooms not being ready for an hour & half past check in, difficult since driving for many hours from out of state with 4 tired kids! First room had No water or refrigerator in working condition, so had to Repack and move to another double room . Pool was huge but VERY ..."

Reviewed on Aug 21, 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
$109 nightly
The price is $121 total per night from Aug 31 to Sep 1
$121 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Very nice property and location. Very accommodating and the staff was professional and courteous."

Reviewed on Aug 24, 2025

Hilton Garden Inn Frederick
See all 314 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.

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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 $156 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.