New Windsor Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AED 148 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best New Windsor Vacation Packages

New Windsor Hotel Deals

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 AED 371 per night from Apr 23 to Apr 24
AED 371
AED 428 total
includes taxes & fees
23 Apr - 24 Apr
8/10 Very Good! (1,001 reviews)
"Rooms need microwaves. WiFi is spotty. Staff is very nice. Breakfast has a good variety. Should keep coffee, cream, and sugar available to guests 24/7."

Reviewed on 14 April 2025

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 AED 297 per night from Apr 28 to Apr 29
AED 297
AED 330 total
includes taxes & fees
28 Apr - 29 Apr
8.2/10 Very Good! (950 reviews)
"Clean, everything we needed, nice budget hotel close to food, gas and shopping."

Reviewed on 15 April 2025

Country Inn & Suites by Radisson, Frederick, MD
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 AED 603 per night from May 4 to May 5
AED 603
AED 670 total
includes taxes & fees
4 May - 5 May
9.2/10 Wonderful! (1,002 reviews)
"Very nice faculties. Shops in walking distance. Not far from battle fields and museums"

Reviewed on 13 April 2025

Inn at Cemetery Hill
See all 284 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.

Frequently asked questions

How much does a New Windsor vacation package cost?
You can snap up a vacation package to this destination 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, February and April. You’ll usually find better rates on hotels and airfares during these months — ideal for travelers wishing to save money.
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.
How to plan a trip to New Windsor?

  1. Choose your dates: The things you want to do in New Windsor and your preferred season will help you decide when to get away.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to put aside for your trip to New Windsor. Then, choose a hotel that fits your budget, whether that’s a wallet-friendly stay or a high-end retreat.
  3. Decide how many days away: Start by making a list of all the activities and attractions you want to experience in New Windsor. Then, estimate how long you’ll need at each, as well as any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that’s left is to choose a New Windsor vacation package that brings all your bookings together.

Discover the most popular places to visit in New Windsor

Old Westminster Winery

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