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.
Planet Hollywood Resort & Casino
Las Vegas Strip
€949
per person
24 Oct - 30 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Las Vegas (LAS)
8.4/10 Very good! (24,416 reviews)
Thanks to the guest agent Marilyn! She was very professional and knowledgeable also recommended a room with an incredible view of the heart of the strip. We were not disappointed. Night time entertainment in the casino was extraordinary. Great DJ! He had even the seniors nodding their head and singing along, lol!!
Reviewed on 1 Sept 2026
Pelican Hotel
South Beach
€1,255
per person
5 Nov - 12 Nov
found 12 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.2/10 Wonderful! (499 reviews)
I’ve stayed in several hotels in South Beach and the Pelican is the best. By far the best. The food is excellent and the staff is so friendly and helpful. For the price, it is a superb value. Plus it is a smaller hotel which means it is not overrun with visitors.
Reviewed on 31 Aug 2026
Top hotels in Windsor
Manoir Des Sables, an Ascend Collection Hotel
90 Des Jardins Ave. Orford QC
Fully refundable
€90
21 Sept - 22 Sept
includes taxes & fees
Hotel Cheribourg, an Ascend Collection Hotel
2603 Chemin Du Parc Orford QC
Fully refundableReserve now, pay when you stay
€80
21 Sept - 22 Sept
includes taxes & fees
Hôtel Le Président
3535, rue King Ouest Sherbrooke QC
Fully refundableReserve now, pay when you stay
€111
13 Sept - 14 Sept
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.
Stay near popular Windsor attractions
le Parc Historique de la Poudriere de Windsor
Find out about the history of Windsor with a stop at le Parc Historique de la Poudriere de Windsor. You can enjoy the restaurants while in the area.
Frequently asked questions
How much does a Windsor holiday package cost?
You'll find cheap prices from €701 on Expedia for your Windsor getaway. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
January, February and November are the best times to look for cheap Windsor holiday packages. Opting to travel in less busy periods means you can typically find better prices on accommodation and flights.
How many days is enough for Windsor?
Generally, a handful of days is enough to visit the main sights during your Windsor holiday. However, if you want to have more time to relax or go on day tours, think about extending your itinerary.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Windsor package deal straight away, just change your dates and search again. Keep in mind 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?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a customised Windsor holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Windsor?
If you're planning a spontaneous Windsor holiday, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Windsor?
- Choose your travel dates: The things you plan to do in Windsor and your preferred season can help you decide when to travel.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and flights. Your hotel will likely be the biggest expense during your trip to Windsor.
- Decide how long to go for: Now that you're up to speed on Windsor, you can figure out the ideal length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to see.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Windsor holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
