New Windsor Vacations

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Find the Best New Windsor Vacation Packages

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
The price is AEDĀ 446 per night from Aug 9 to Aug 10
AEDĀ 446
AEDĀ 496 total
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (1,021 reviews)
"Very good location and cute but rooms were small. Beds were hard and there was dust on furniture and out feet were dirty from walking on the floors in the room. Could be cleaner."

Reviewed on 17 July 2026

Inn at Cemetery Hill
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
The price is AEDĀ 360 per night from Jul 23 to Jul 24
AEDĀ 360
AEDĀ 416 total
23 Jul - 24 Jul
includes taxes & fees
8.2/10 Very Good! (1,340 reviews)
"Itā€™s super cleaning and organized the staff very professional as well"

Reviewed on 16 July 2026

Hyatt Place Baltimore/Owings Mills
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
The price is AEDĀ 323 per night from Aug 16 to Aug 17
AEDĀ 323
AEDĀ 358 total
16 Aug - 17 Aug
includes taxes & fees
8.2/10 Very Good! (1,349 reviews)
"My family and I frequent this hotel at least 3-5 times a year. Itā€™s very clean, the staff is very nice and helpful."

Reviewed on 16 July 2026

Country Inn & Suites by Radisson, Frederick, MD
See all 346 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.

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

Frequently asked questions

How much does a New Windsor vacation package cost?
You can pick up a vacation package to this top destination on Expedia. But how much your vacation to New Windsor costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to New Windsor?
If you'd like to snag a cheap New Windsor vacation package, consider traveling in January, February and April. You'll usually find better prices on airfares and hotels during these months ā€” perfect for a budget-friendly getaway.
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 some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect New Windsor package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your New Windsor getaway 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 escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to New Windsor?
If you've got your New Windsor vacation dates finalized, book as early as you can to bag some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to New Windsor?

  1. Choose your travel dates: The things you want to do in New Windsor and your preferred season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will probably be the biggest expense during your trip to New Windsor.
  3. Decide your trip length: Think about how much time you want to spend discovering New Windsor. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a New Windsor vacation package that brings all your bookings together.