New Windsor Vacations from $313

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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
Price was $531, price is now $313 per person
$313
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,002 reviews)

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 $666, price is now $445 per person
$445
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)
Nothing like any Sofitel I knew in other cities and worse than few years ago when I visited here. Bed sheaths were unclean( stain on it!) and even though I took them off, they put them back again. Will not come back here.

Reviewed on Nov 3, 2026

Harbor free indoor parking

Harbor free indoor parking

4 out of 5
Downtown Baltimore
Price was $575, price is now $388 per person
$388
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
No reviews

Eaton DC

Eaton DC

4.5 out of 5
Downtown Washington D.C.
Price was $660, price is now $452 per person
$452
per person
Jan 12 - Jan 17
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,633 reviews)
Great stay

Reviewed on Nov 1, 2026

Convention center Indoor free parking

Convention center Indoor free parking

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $460, price is now $316 per person
$316
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
No 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
$197 nightly
The price is $210 total per night from Dec 5 to Dec 6
$210 total
Dec 5 - Dec 6
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
$136 nightly
The price is $154 total per night from Nov 17 to Nov 18
$154 total
Nov 17 - Nov 18
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
$101 nightly
The price is $112 total per night from Nov 24 to Nov 25
$112 total
Nov 24 - Nov 25
Total with taxes and fees
9.2/10 Wonderful! (1,107 reviews)
"Great hotel in a great location. Rooms are well maintained and super clean. Staff was very friendly. Only thing I wasn’t aware of was a $50 hold that needed to be done when you check in"

Reviewed on Nov 4, 2026

Inn at Cemetery Hill
See all 340 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 $313 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.