New Windsor Vacations from $174
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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.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
$847
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,261 reviews)
DO NOT PAY FOR BREAKFAST!!!!! I just stayed two nights at the Sofitel Hotel in Washington DC. Everything was perfect until breakfast time the following morning.
Both days we had to wait over half hour to be seated for breakfast. I almost lost my tour. Besides waiting for a long time. Food took another 20 minutes to arrive at our table. And another 10 minutes to get the check. Clearly they are under staff.
The second morning, the line for breakfast was longer. We needed to drive fours hours to go back home. So I went to the front desk and asked to be credited back for one day for our breakfast since we couldn't wait for over one hour and a half to have breakfast. They told me NO, the it was part of a package and I said, I selected the breakfast option. I paid more to have the breakfast, is not like the hotel includes the breakfast in your rate. The breakfast is a sit down breakfast, it is not a buffet. The manager said that he can only do a room service and that it was going to be faster. He said take it or leave it. He said if "you don't use it you loose it", What type of customer service is that. I saw a lot of people complaining. Some people left saying that they will dispute the charges.
The Hotel is in a perfect location, everything was clean. I have no other complain besides the breakfast taking a long time. Tourist usually have tours schedules and breakfast should not take this long. I am very disappointed at this hotel brand.
Reviewed on Sep 7, 2026
Kellogg Conference Hotel at Gallaudet University
Northeast
$514
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,005 reviews)
The room had a good massage chair that worked well! The first day there was a fishy smell all across the property and the room smelled like it had been smoked in.
Reviewed on Sep 7, 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
Inn at Cemetery Hill
613 Baltimore St Gettysburg PA
$142 nightly
$158 total
Sep 13 - Sep 14
Total with taxes and fees
9.4/10 Exceptional! (1,096 reviews)
"Nice little spot in the middle of town, very homey feel."
Reviewed on Sep 8, 2026
Hyatt Place Baltimore/Owings Mills
4730 Painters Mill Rd Owings Mills MD
Fully refundableReserve now, pay when you stay
$98 nightly
$113 total
Sep 15 - Sep 16
Total with taxes and fees
Best Western Historic Frederick
420 Prospect Blvd Frederick MD
Fully refundableReserve now, pay when you stay
$82 nightly
$91 total
Sep 16 - Sep 17
Total with taxes and fees
8/10 Very Good! (1,005 reviews)
"The television was almost uselessl The services it subscribed to had a terrible choice of channels. The machine itself was hard to use. The bathroom could have used an electric outlet for a night light."
Reviewed on Sep 7, 2026
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 $174 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.
