Windsor Holidays
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Windsor Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Dutch Hotel Long Island City New York , Belvilla District 6 Formerly Sonder
Queens
S$1,040
per person
22 Sept - 25 Sept
found 2 hours ago
Return flight included
Toronto (YYZ) to New York (JFK)
7/10 Good! (452 reviews)
Upon checking in, I had to be transferred two times because the room’s AC condensation was dripping onto the floor and made it wet which I slipped on. I caught myself. The second room was the same situation so I was transferred into a third room..Naveen the man that was helping me was the only good part of this experience. We tried his best although was just by himself there is basically no other help at this property other than Navene. The gym is not operational and that was not stated the rooms however our actually nice although my TV was not working..
Reviewed on 8 Aug, 2026
Hotel Riu Plaza New York Times Square
Manhattan
S$1,918
per person
22 Sept - 25 Sept
found 2 hours ago
Return flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (3,255 reviews)
Loved staying at this hotel. Location was perfect to Times Square. The room was clean and the views were stunning. Breakfast was top class. No complaints.
Reviewed on 9 Aug, 2026
YOTEL New York Times Square
Manhattan
S$1,288
per person
22 Sept - 25 Sept
found 2 hours ago
Return flight included
Toronto (YYZ) to New York (JFK)
7.8/10 Good! (2,955 reviews)
Millie, the cleaner, was very helpful. However, I’m not sure the reception staff really wanted to be there. The lady at reception was yawning while talking to us, sitting cross-legged, and generally seemed like she didn’t enjoy what she was doing. The other guy wasn’t able to help us with the check-in, and when we reached the check-in counter, there were no key cards available.
Overall, I had the feeling that I was disturbing them during my stay rather than being welcomed as a guest.
Reviewed on 8 Aug, 2026
Top hotels in Windsor
Hyatt Regency Princeton
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
S$173
7 Sept - 8 Sept
includes taxes & fees
Hilton East Brunswick Hotel & Executive Meeting Center
3 Tower Center Blvd East Brunswick NJ
Fully refundableReserve now, pay when you stay
S$161
13 Aug - 14 Aug
includes taxes & fees
DoubleTree by Hilton Princeton
4355 US Highway 1 at Ridge Rd. Princeton NJ
Fully refundableReserve now, pay when you stay
S$149
23 Aug - 24 Aug
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 holiday package cost?
You can snap up a holiday package to this top destination from S$1,040 on Expedia. But how much your holiday 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 holiday 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 holiday. 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 holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalise 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 holiday 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, favourite 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 customised Windsor holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
