New Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your New Windsor Vacation
There's no better way to travel than with one of our vacation packages to New Windsor. The rich history and spectacular views are two of the convincing reasons to spend some time in this captivating city. Dia Beacon, Storm King Art Center and Ice Time Sports Complex are just some of the attractions you'll want to explore during your trip to New Windsor. A couple of quick clicks is all it takes to put together a tailored New Windsor vacation on Expedia.
Top New Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Monroe - Woodbury
Price was CA $1,148, price is now CA $1,000 per person
CA $1,000
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.4/10 Exceptional! (1,046 reviews)
I was there for 1 night and didn’t do much just sleep for the night but it was pretty good.
Reviewed on Apr 9, 2026
New Windsor Hotel Deals
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave New Windsor NY
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from May 10 to May 11
CA $130
CA $147 total
May 10 - May 11
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
Yes
Reviewed on Apr 12, 2026
Homewood Suites Stewart Airport
180 Breunig Rd New Windsor NY
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Apr 19 to Apr 20
CA $196
CA $222 total
Apr 19 - Apr 20
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
The hotel is clean and well maintained and the breakfast was standard but pretty good. When I checked in I noticed the room was not what I reserved. The person at the desk refused to help. She said it’s Expedia’s fault and she can’t do anything about it. She said next time don’t use Expedia and you’ll ...
Reviewed on Apr 12, 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
The price is CA $147 per night from Apr 28 to Apr 29
CA $147
CA $174 total
Apr 28 - Apr 29
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
Breakfast is set up as a buffet style. The breakfast is actually very good
Reviewed on Apr 12, 2026
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.
What to do in New Windsor
Bear Mountain State Park+ BeaconTown 1-Day Tour From NY
CA $129
per adult
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
CA $1,070
per traveller
Explore a world of travel with Expedia
- Hotels near Bannerman Castle
- B&B in Beacon
- Cabin Rentals in Beacon
- Castles in Beacon
- Guest Houses in Beacon
- Holiday Park Resorts in Beacon
- Cheap Hotels in Beacon
- Family Hotels in Beacon
- Lgbt Friendly Hotels in Beacon
- Luxury Hotels in Beacon
- Beacon Hotels
- Motels in Beacon
- Resorts in Beacon
- B&B in Cornwall-on-Hudson
- Beach Hotel Hotels in Cornwall-on-Hudson
- Boutique Hotels in Cornwall-on-Hudson
- Cheap Hotels in Cornwall-on-Hudson
- Historic Hotels in Cornwall-on-Hudson
- Hotels with a Pool in Cornwall-on-Hudson
- Luxury Hotels in Cornwall-on-Hudson
- Marriott Hotels & Resorts in Cornwall-on-Hudson
- Pet-Friendly Hotels in Cornwall-on-Hudson
- Spa Hotels in Cornwall-on-Hudson
- Cornwall-On-Hudson Hotels
- Resorts in Cornwall-on-Hudson
- Hotels near Dia Beacon
- Firthcliffe Hotels
- Inns in Firthcliffe
- Hotels near Mount Saint Mary's College Newburgh
- New York Hotels
- Hotels near New York Military Academy
- B&B in Newburgh
- Cottages in Newburgh
- Beach Hotel Hotels in Newburgh
- Best Western Hotels in Newburgh
- Boutique Hotels in Newburgh
- Cheap Hotels in Newburgh
- Historic Hotels in Newburgh
- Hotels with a Pool in Newburgh
- Hotels with Free Airport Shuttle in Newburgh
- Hotels with Free Parking in Newburgh
- Hotels with an Indoor Pool in Newburgh
- Hotels with Kitchenettes in Newburgh
- Luxury Hotels in Newburgh
- Pet-Friendly Hotels in Newburgh
- Romantic Hotels in Newburgh
- Spa Hotels in Newburgh
- Newburgh Hotels
- Motels in Newburgh
- Vails Gate Hotels
- Resorts in Vails Gate
- Bannerman Castle
- Bear Mountain State Park
- Bear Mountain Vacations
- Brewster Vacations
- Charles Point Pier Park
- Cornwall Vacations
- Cronomer Hill Park
- Croton Landing Park
- Culinary Institute of America
- Eleanor Roosevelt National Historic Site
- Franklin D. Roosevelt Presidential Library and Museum
- Hudson River Valley Vacations
- Hudson Valley Vacations
- Hyde Park Station
- Ice Time Sports Complex
- Legoland® New York
- Lake Tiorati Beach
- Michie Stadium
- Milton Vacations
- Mohonk Preserve Visitor Center
- Mount Peter Ski Area
- Visit Newburgh
- Orange County Fair Speedway
- Orange Lake Vacations
- Palaia Vineyards Winery
- Peekskill Vacations
- Poughkeepsie Vacations
- Stormville Airport Antique Show & Flea Market
- Tuxedo Park Vacations
- West Point Vacations
- Woodbury Common Premium Outlets
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
