Windsor Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
Top Flight + Hotel Deals in Windsor
Price found within the past 48 hours. Click for updated prices.
NobleDEN Hotel
Manhattan
€1,605
per person
12 Oct - 19 Oct
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (1,662 reviews)
Amazing staff, great location, spectacular views from the rooftop patio area. Sits right next to the Da Nico restaurant with the best food in Little Italy. I look forward to my next visit!
Reviewed on 1 Sept 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
€1,732
per person
12 Oct - 19 Oct
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,936 reviews)
This is the the best and most convenient location to stay around midtown time square area……you won’t ever regret this decision
Reviewed on 1 Sept 2026
The High Line Hotel
Manhattan
€2,223
per person
13 Oct - 20 Oct
found 7 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,004 reviews)
When I arrived, which was a half hour past check-in time, the room was still not ready. I also requested a high-floor, which they said they could accomodate, and then could not. FInally, on Hotels.com it banners that pets stay free. They do not.
Reviewed on 1 Sept 2026
Top hotels in Windsor
Hyatt Regency Princeton
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
€116
13 Sept - 14 Sept
includes taxes & fees
8.8/10 Excellent! (1,413 reviews)
"Had to request change of room for the first one smelled horrible. Some of le exit signs fixtures require better fixation and more aesthetic appearance. The carpets definitely need a deep cleaning"
Reviewed on 2 Sept 2026
Hilton East Brunswick Hotel & Executive Meeting Center
3 Tower Center Blvd East Brunswick NJ
Fully refundableReserve now, pay when you stay
€112
20 Sept - 21 Sept
includes taxes & fees
The Heldrich Hotel
10 Livingston Avenue New Brunswick NJ
Fully refundableReserve now, pay when you stay
€118
16 Sept - 17 Sept
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"Na"
Reviewed on 31 Aug 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.
Frequently asked questions
How much does a Windsor holiday package cost?
You can snap up a holiday package to this top destination from €1,605 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.
