New Windsor Vacation Packages

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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.

Top New Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ulysses, an Ash Hotel

Ulysses, an Ash Hotel

4 out of 5
Midtown
per person
Feb. 27 - Mar. 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (635 reviews)
Hotel has a cool vibe Friendly and helpful staff

Reviewed on Jan. 4, 2025

The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Feb. 9 - Feb. 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Washington (DCA)
8.8/10 Excellent! (1,534 reviews)
The room was beautiful, with coffee, little handcrafted chocolate truffle, water, spacious bathroom with great mirrors for putting on makeup, well lit, and with thoughful supplies of slippers and robes. I particularly loved the speakeasy downstairs. I did not get to check out the rooftop patio but I hope to return and do so one day. It is unique and idyllic. I will stay here again!

Reviewed on Jan. 2, 2025

Atlantic Sands Hotel & Conference Center

Atlantic Sands Hotel & Conference Center

3.5 out of 5
North Rehoboth
per person
Mar. 8 - Mar. 15
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
8.4/10 Very Good! (1,314 reviews)
Xmas decor was beautiful.

Reviewed on Jan. 5, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
per person
Feb. 8 - Feb. 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Washington (DCA)
9.4/10 Exceptional! (1,009 reviews)
I love the views. But it has changed since the property was the mandarin oriental. It needs to be renovated and updated.

Reviewed on Jan. 2, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
per person
Feb. 9 - Feb. 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Washington (DCA)
8.4/10 Very Good! (1,001 reviews)
The hotel is very average. For the amount we paid per night I was expecting way more. The hotel is outdated, the rooms and service were average. Not really worth it in my opinion.

Reviewed on Jan. 2, 2025

Ready to book your vacation to New Windsor?

 

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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 CA $127 per night from Jan. 12 to Jan. 13
CA $127
CA $147 total
includes taxes & fees
Jan 12 - Jan 13
8/10 Very Good! (1,010 reviews)
"Hotel very clean,no parking issues,no negative results at all."

Reviewed on Jan. 2, 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 CA $117 per night from Jan. 16 to Jan. 17
CA $117
CA $130 total
includes taxes & fees
Jan 16 - Jan 17
8.4/10 Very Good! (1,006 reviews)
"The staff the room and the overall experience"

Reviewed on Jan. 2, 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 CA $145 per night from Jan. 26 to Jan. 27
CA $145
CA $161 total
includes taxes & fees
Jan 26 - Jan 27
8.8/10 Excellent! (1,003 reviews)
"Great Stay!!"

Reviewed on Jan. 4, 2025

Hilton Garden Inn Frederick
See all 286 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a New Windsor vacation package cost?
You can snap up a vacation package to this destination from CA $785 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 many days is enough for New Windsor?
Usually, a handful of days is enough to check out the major attractions during your New Windsor vacation. 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 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.