New Windsor Vacations from $307
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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.
Eaton DC
Downtown Washington D.C.
$307
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,609 reviews)
First, the best thing about this hotel is the staff. Always helpful and they responded to any request with alacrity. For example, when my daughter and I came back after a wedding, she called to have ice brought up to our room. During her conversation, she mentioned that her feet were hurting after all that dancing. When the staff member appeared at our door, he carried not only a bucket of ice, but a bag (triple bagged) of ice for her aches.
The hotel is a retro boutique hotel. When I entered my room, there was a turntable on the shelf as well as several vinyl records. Old photos decorated the walls. Bathroom fixtures were also old fashioned, although they functioned as well any more modern looking ones.
Returning after lunch, I noticed that there was a radio station broadcasting from the lobby. I particularly noticed it, because when I walked in, I saw a light on a recording booth that said "On Air."
A thoroughly pleasant stay!!
Reviewed on Oct 13, 2026
Kellogg Conference Hotel at Gallaudet University
Northeast
$321
per person
Nov 19 - Nov 23
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,011 reviews)
Very nice and quiet place, very close to the conference downtown DC well kept grounds as well.
I’d stay again and pricing is very good compared to downtown prices as well!
Reviewed on Oct 13, 2026
The Churchill Hotel near Embassy Row
Northwest
$484
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,018 reviews)
For such a historic hotel, it was well kept. The breakfast was delicious, the room was spacious, and I felt like a well-respected guest for the night.
Reviewed on Oct 13, 2026
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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.
New Windsor Hotel Deals
Sunday Morning at Savannahs
111 South Springdale Avenue, New Windsor New Windsor MD
$139 nightly
$148 total
Oct 16 - Oct 17
Total with taxes and fees
10/10 Exceptional! (1 review)
"Perfect getaway!"
Reviewed on Sep 27, 2026
Best Western Historic Frederick
420 Prospect Blvd Frederick MD
Fully refundableReserve now, pay when you stay
$77 nightly
$86 total
Oct 25 - Oct 26
Total with taxes and fees
8/10 Very Good! (1,017 reviews)
"Overall stay was 3 stars. Although the staff at the front desk was nice, they could/would not provide smaller bills for the vending machine after the credit card scanner wouldn't work. Breakfast was good, and the fresh yogurt machine was a plus. In the room, there were smells from the AC, heat wouldn't ..."
Reviewed on Oct 13, 2026
Inn at Cemetery Hill
613 Baltimore St Gettysburg PA
$162 nightly
$179 total
Nov 1 - Nov 2
Total with taxes and fees
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 $307 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.