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.
Super 8 By Wyndham Baltimore Northwest

Super 8 By Wyndham Baltimore Northwest

2 out of 5
Woodlawn
Price was CA $1,327, price is now CA $933 per person
CA $933
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.2/10 Very good! (1,047 reviews)
I got charged after getting kicked out.

Reviewed on Jul 4, 2026

Element by Marriott Arundel Mills BWI Airport

Element by Marriott Arundel Mills BWI Airport

3 out of 5
Arundel Mills
Price was CA $1,513, price is now CA $995 per person
CA $995
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (1,006 reviews)
It was ok. I liked the aesthetic of the lobby. Couldn’t use the pool it was closed for renovations. The room was alright. Kinda small. I wouldn’t put more than 2 in there. The bed was comfy. The bathroom was small. It had a rain shower. I hate rain showers. The shower had no racks so I had to sit my stuff on the floor in the shower. Not much counter space The doors to the room and the bathroom are super heavy. The bathroom floor got really wet from the shower. But the water was nice and hot. I really liked the kitchenette area. It was a nice size mini fridge The breakfast was ok. I would stay here again.

Reviewed on Jun 29, 2026

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $1,622, price is now CA $1,091 per person
CA $1,091
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (1,000 reviews)
The Sheraton is in a great location, we were there for a family wedding and close to everything. Parking was very easy on site (for a fee). There was no breakfast included so we didn’t make it down to the restaurant but there is a very convenient Starbucks in the lobby. The only negative I would say is when you get off the elevator on the floor it felt very humid and hot bc there seemed to always be someone doing laundry. Highly recommend

Reviewed on Jul 2, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was CA $1,629, price is now CA $1,116 per person
CA $1,116
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.2/10 Very good! (2,806 reviews)
Very clean room

Reviewed on Jul 4, 2026

Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was CA $1,370, price is now CA $963 per person
CA $963
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.6/10 Excellent! (1,000 reviews)
Solo travel for work. Great stay!

Reviewed on Jul 2, 2026

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 $139 per night from Jul 12 to Jul 13
CA $139
CA $161 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very good! (1,322 reviews)
"Coffee machine was not working."

Reviewed on Jul 4, 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 CA $131 per night from Jul 29 to Jul 30
CA $131
CA $145 total
Jul 29 - Jul 30
includes taxes & fees
8.2/10 Very good! (1,339 reviews)
"Upon arrival, the room was NOT available to check in at 3pm. I was asked to wait until the room was cleaned. That was a HUGH inconvenience because I had traveled the entire morning and was ready to rest! The room was semi clean and the pillows were really small. We made it work for one night."

Reviewed on Jul 4, 2026

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 CA $190 per night from Jul 26 to Jul 27
CA $190
CA $211 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"Great central location right at Cemetary Hill. Many shops, restaurants and memorials within walking distance. Friendly staff, good breakfast options and well kept properly. No pool so if that's a priority this property wont be for you."

Reviewed on Jul 4, 2026

Inn at Cemetery Hill
See all 349 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.
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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 from CA $933 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 travelling in January, February and April. You'll usually find better prices on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for New Windsor?
Usually, a handful of days is enough to check out the top attractions during your New Windsor vacation. However, if you want to have more time to relax or go on day tours, consider extending your trip.
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 travelling 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.

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