Windsor Vacations from ₩656,494
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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
The Latest Windsor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
Manhattan
₩896,000
per person
Oct 18 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,334 reviews)
Very small room, I called down to concierge and they could not understand my Australian accent and decided to just hang up in my ear, I called back and they just dismissed my complaint, I will not recommend this hotel
Reviewed on Sep 4, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
₩797,094
per person
Oct 18 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,936 reviews)
It should be more discount for parking cars nearby of hotel’s guests..
Reviewed on Sep 4, 2026
Find the Best Windsor Vacation Packages
Windsor Hotel Deals
Hyatt Regency Princeton
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
₩160,303
₩183,748 total
Sep 13 - Sep 14
includes taxes & fees
8.8/10 Excellent! (1,419 reviews)
"Very nice and clean."
Reviewed on Sep 4, 2026
Hilton East Brunswick Hotel & Executive Meeting Center
3 Tower Center Blvd East Brunswick NJ
Fully refundableReserve now, pay when you stay
₩154,830
₩177,473 total
Sep 20 - Sep 21
includes taxes & fees
7.4/10 Good! (1,267 reviews)
"Hotel Lobby & entrance is great, very clean & comfortable. Rooms need some renovation and updates. Restaurant options very limited and overpriced compared to other hotels & the quality of the food. Also, the items in the lobby's minimarket are excessively overpriced, $5 for a regular bottle of water!!! ..."
Reviewed on Sep 3, 2026
The Heldrich Hotel
10 Livingston Avenue New Brunswick NJ
Fully refundableReserve now, pay when you stay
₩158,278
₩187,757 total
Sep 27 - Sep 28
includes taxes & fees
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 Windsor vacation package cost?
You can snap up a vacation package to this top destination from ₩656,494 on Expedia. But how much your vacation to Windsor costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Windsor?
January, February and March are the best times to look for cheap Windsor vacation packages. Opting to travel in less busy months means you'll typically find lower prices on hotels and flights.
How many days is enough for Windsor?
Typically, a handful of days is enough to explore the main sights during your Windsor vacation. But if you prefer to have some time to relax or go on day trips, think about extending your itinerary.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Windsor package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalize your Windsor escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you have your Windsor travel dates locked in, book as early as you can to snap up some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Windsor?
- Choose the perfect time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to go to Windsor.
- Set your budget: Factor in costs like food, flights and transportation when working out how much to set aside for your trip to Windsor. Then, pick a property that fits your budget, whether that's an economical stay or a more luxurious getaway.
- Decide your trip length: Consider how long you'd like to spend exploring Windsor. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Windsor vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
