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.
YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
per person
Jun. 5 - Jun. 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.4/10 Very Good! (1,874 reviews)
Hotel was convienient to all attractions. Limited supplies in the room we needed additional towels and washcloths and could not get anyone on the phone to bring to us. Husband went to lobby and got one, only to be taken away in the morning cleaning and not replaced. Also thought the charge for food each day was a bit sketchy - we did not use it nor wanted it. Price was less per night only to be inflated with surcharges making it the same price as other hotels.

Reviewed on Apr. 28, 2025

Airlie Hotel

Airlie Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun. 20 - Jun. 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (280 reviews)
This place is beautiful and amazing. Better than expected. We had a stay.

Reviewed on Mar. 30, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
per person
Jul. 6 - Jul. 12
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Washington (DCA)
8.2/10 Very Good! (1,010 reviews)
Place was nice. Clean comfy, I would take my family there again.

Reviewed on Apr. 29, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
per person
Jun. 5 - Jun. 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,003 reviews)
Comfortable lobby lounge area. Accommodating staff . Location is terrific. Easy access to the new wharf area with wonderful restaurants. And across the street for Starbucks because the only downside is the expensive buffet breakfast which is quite ordinary.

Reviewed on Apr. 26, 2025

The Westin Alexandria Old Town

The Westin Alexandria Old Town

4 out of 5
Eisenhower East
Save 100% on your flight
per person
Jul. 3 - Jul. 10
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9/10 Wonderful! (1,001 reviews)
Awesome place to stay

Reviewed on Apr. 21, 2025

Ready to book your vacation to New Windsor?

 

Choose your dates

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 $140 per night from May 6 to May 7
CA $140
CA $161 total
includes taxes & fees
May 6 - May 7
8/10 Very Good! (1,010 reviews)
"We were in another location and tHyatt literally saved the day as we needed to leave that terrible place. They allowed us to chack in early adn were very sweet. Every employee we interacred with showed kindness. I am forever grateful."

Reviewed on Apr. 27, 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 $115 per night from May 18 to May 19
CA $115
CA $127 total
includes taxes & fees
May 18 - May 19
8.2/10 Very Good! (1,007 reviews)
"This was reasonably priced, in a great location for me to get to a wedding venue, and it had everything I needed."

Reviewed on Apr. 25, 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
The price is CA $216 per night from May 13 to May 14
CA $216
CA $240 total
includes taxes & fees
May 13 - May 14
9.2/10 Wonderful! (1,011 reviews)
"One of the most amazing hotel staff’s ever."

Reviewed on Apr. 28, 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.

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 $898 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.