Windsor Holidays from AU$2,803
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Your Windsor Holiday
Organising your next travel adventure is a breeze with a Windsor holiday package. The neighbourhood of Princeton Meadows, which is good for golfing, makes a good launchpad to uncover the marvels of this lively city. Fill your trip to Windsor with tours of some of its most popular attractions. Where to first? Make a move for Working Dog Winery. Your ideal Windsor holiday is a couple of clicks away. Browse hotels, airfares and more on Expedia for a trip that's tailored just for you.
The Latest Windsor Holiday Deals
Price found within the past 48 hours. Click for updated prices.
42 Hotel
AU$2,803
per person
1 Nov - 8 Nov
found 18 hours ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (944 reviews)
I stayed here for a night while moving my daughter into college nearby. The hotel is amazing. Everything about it was wonderful. From the staff, to the rooms, to the amenities. Breakfast was delicious. There’s no allocated parking but plenty of street parking in the neighborhood. Definitely will be staying here in all future visits to Brooklyn.
Reviewed on 17 Aug 2026
The Fifth Avenue Hotel
Manhattan
AU$6,132
per person
1 Nov - 8 Nov
found 18 hours ago
Return flight included
Sydney (SYD) to New York (JFK)
9.6/10 Exceptional! (262 reviews)
Lovely, attentive staff and a genuinely helpful concierge who booked us a fantastic dinner.
I really can’t say enough about the entire staff from the moment we checking until to the end. This Hotel has One the most beautiful restaurant with fantastic service and food. I truly loved my room . The maid was keeping the room clean and paid so much attention to little details that my wife and I cared so much about. . Five star and Fantastic breakfast and dinner!!! All the waiters staff very professional and friendly.
I highly recommend this hotel.
Reviewed on 12 Aug 2026
NobleDEN Hotel
Manhattan
AU$3,333
per person
1 Nov - 8 Nov
found 18 hours ago
Return flight included
Sydney (SYD) to New York (JFK)
9.8/10 Exceptional! (1,634 reviews)
NobleDEN is a great hotel placed perfectly near little Italy and Chinatown. Subway stops were not far away you are surrounded by great food options. The staff were very nice, friendly and accommodating. Always greeted you when you left and returned. Would stay here again. The view from the roof was pretty and a nice spot to relax. The rooms were clean and kept tidy. House keeping was friendly and helpful.
Reviewed on 17 Aug 2026
Margaritaville Resort Times Square
Manhattan
AU$3,071
per person
1 Nov - 8 Nov
found 18 hours ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (4,305 reviews)
Fun pool and rooftop bars. Love that you can see the Times Square ball from the rooftop bar.
Food was average with chicken tenders being chewy and a dip over hot from the microwave.
Reviewed on 18 Aug 2026
Windsor Holiday
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Mercer Airport (TTN) |
Max Temp Winter | 4ºC |
Max Temp Summer | 27ºC |
Our pick of the best Windsor Hotel Deals
Hyatt Regency Princeton
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
AU$190
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
AU$177
19 Aug - 20 Aug
includes taxes & fees
7.4/10 Good! (1,240 reviews)
"Did not attend restaurants"
Reviewed on 18 Aug 2026
Holiday Inn East Windsor - Cranbury Area by IHG
399 Monmouth St Hightstown NJ
Fully refundable
AU$156
30 Aug - 31 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 AU$2,803 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.
