New Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in New Windsor

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 2.628.200 ₫ per night from 7 Sept to 8 Sept
2.628.200 ₫
3.035.571 ₫ total
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very Good! (1,082 reviews)
"The only thing I didn’t like was the breakfast in the TV TV is way too update it"

Reviewed on 11 Aug 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 2.211.630 ₫ per night from 21 Aug to 22 Aug
2.211.630 ₫
2.454.910 ₫ total
21 Aug - 22 Aug
includes taxes & fees
8.2/10 Very Good! (1,078 reviews)
Highly recommend
"One of the best and decent prices. Breakfast was a little downhill from last year."

Reviewed on 12 Aug 2025

Country Inn & Suites by Radisson, Frederick, MD
Hilton Garden Inn Frederick

Hilton Garden Inn Frederick

3 out of 5
7226 Corporate Ct, Frederick, MD
Fully refundableReserve now, pay when you stay
The price is 2.770.123 ₫ per night from 31 Aug to 1 Sept
2.770.123 ₫
3.074.836 ₫ total
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
One night stay
"The bartender was awesome! Everyone was super nice and friendly. The only downfall too me was that beds were hard. Its totally a me problem, but yeah,they could have been softer."

Reviewed on 11 Aug 2025

Hilton Garden Inn Frederick
See all 314 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 holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday 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 holiday package, consider visiting in January, February and April. You'll usually find better rates on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for New Windsor?
Usually, a handful of days is enough to check out the major attractions during your New Windsor holiday. However, if you'd like to have some time to chill out or go on day trips, think about extending your itinerary.
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 holiday as a package?
You can enjoy significant savings on your New Windsor retreat by booking a personalised holiday 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 holiday 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 holiday package that brings all your bookings together.