New Windsor Vacations from $198

Book a Hotel + Flight or Car together to unlock savings

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 Rendale Washington DC

Hotel Rendale Washington DC

3.5 out of 5
Northwest
Save 100% on your flight
Price was $293, price is now $198 per person
$198
per person
Aug 31 - Sep 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
7.8/10 Good! (1,459 reviews)
Overalls good experience. Basic Coffee ☕️ maker would make our stay little more comfortable.

Reviewed on Jun 8, 2026

Rachael's Inner Harbor Boutique Inn

Rachael's Inner Harbor Boutique Inn

3 out of 5
Ridgely's Delight
Save 100% on your flight
Price was $945, price is now $629 per person
$629
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
10/10 Exceptional! (4 reviews)
Beautiful and spacious

Reviewed on May 21, 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 $685, price is now $459 per person
$459
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,001 reviews)
We really liked the size of the room. It was in a nice walkable location and it was clean. Quick trip and very happy.

Reviewed on Jun 14, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $485, price is now $328 per person
$328
per person
Sep 4 - Sep 7
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,012 reviews)
This is a safe, nice hotel on a college campus in a great location of DC. The staff was friendly and professional. The only thing we had an issue is with allergies. Seemed like a dust issue as the rooms all have the air conditioning with recycled air. Overall great property.

Reviewed on Jun 15, 2026

Hotel Washington

Hotel Washington

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $689, price is now $469 per person
$469
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (2,422 reviews)
Everything was perfect

Reviewed on Jun 13, 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
$146 nightly
The price is $162 total per night from Jun 17 to Jun 18
$162 total
Jun 17 - Jun 18
Total with taxes and fees
9.4/10 Exceptional! (1,048 reviews)
"Great location, thankful for free parking, and helpful staff."

Reviewed on Jun 15, 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
$91 nightly
The price is $101 total per night from Jul 12 to Jul 13
$101 total
Jul 12 - Jul 13
Total with taxes and fees
8.2/10 Very Good! (1,333 reviews)
"This is an older hotel obviously. The staff was excellent, the room was okay and the breakfast was very limited. We probably won't stay there again but might be fine for most people."

Reviewed on Jun 15, 2026

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
$98 nightly
The price is $113 total per night from Jun 28 to Jun 29
$113 total
Jun 28 - Jun 29
Total with taxes and fees
8.2/10 Very Good! (1,297 reviews)
"Unfortunately, the room was humid. The carpet was damp near the sink. The carpet and couch had stains. The room phone was visibly dirty."

Reviewed on Jun 15, 2026

Hyatt Place Baltimore/Owings Mills
See all 349 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 $198 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.