Windsor Holidays

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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, 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.
Albergo Etico Roma

Albergo Etico Roma

3 out of 5
Flaminio
Save 100% on your flight
per person
26 Aug - 29 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Rome (FCO)
9.6/10 Exceptional! (266 reviews)
The only negative is there was an event one of our nights that went till midnight. It was very loud and hard to sleep. The breakfast was excellent and the service was excellent!

Reviewed on 11 Jul 2025

One Bedroom Balcony 1.5 BTH Palms Place StripSuite

One Bedroom Balcony 1.5 BTH Palms Place StripSuite

4.5 out of 5
per person
28 Aug - 4 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Las Vegas (LAS)
No reviews
Horseshoe Las Vegas

Horseshoe Las Vegas

4 out of 5
Las Vegas Strip
per person
10 Sept - 17 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Las Vegas (LAS)
7.8/10 Good! (10,356 reviews)
It was close to evening we wanted to experience.

Reviewed on 20 Jul 2025

Planet Hollywood Resort & Casino

Planet Hollywood Resort & Casino

4 out of 5
Las Vegas Strip
Save 100% on your flight
per person
25 Sept - 30 Sept
found 23 hours ago
Return direct flight included
Dublin (DUB) to Las Vegas (LAS)
8/10 Very Good! (17,363 reviews)
The elevator and room keys kept needing replacement. Other than that it was a great stay!

Reviewed on 20 Jul 2025

Treasure Island - TI Las Vegas Hotel & Casino

Treasure Island - TI Las Vegas Hotel & Casino

4 out of 5
Las Vegas Strip
per person
10 Sept - 17 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Las Vegas (LAS)
8.4/10 Very Good! (28,817 reviews)
There was a plumbing issue that made our room smell like sewage. It was extremely unbearable that we were forced to wait outside. Had to wait close to an hour until maintenance came.

Reviewed on 20 Jul 2025

Top hotels in Windsor

Manoir des Sables Hôtel & Golf

Manoir des Sables Hôtel & Golf

4 out of 5
90 Des Jardins Ave., Orford, QC
Fully refundable
8.2/10 Very Good! (1,007 reviews)
"..."

Reviewed on 14 Jul 2025

Get rates
Manoir des Sables Hôtel & Golf
Grand Times Hotel Sherbrooke

Grand Times Hotel Sherbrooke

4 out of 5
1, rue Belvedere Sud, Sherbrooke, QC
Fully refundable
8.2/10 Very Good! (1,007 reviews)
"The location of the property is perfect. The hotel is beautiful. The room is spacious and nicely decorated. The room we stayed has a fantastic view of the lake. Staff at the desk and housekeeping are friendly and helpful. Food is available at Marché de la Gare or shops near by."

Reviewed on 14 Jul 2025

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Grand Times Hotel Sherbrooke
Hôtel Chéribourg

Hôtel Chéribourg

4 out of 5
2603 Chemin Du Parc, Orford, QC
Fully refundableReserve now, pay when you stay
8/10 Very Good! (1,201 reviews)
"Good"

Reviewed on 19 Jul 2025

Get rates
Hôtel Chéribourg
See all 174 properties in Windsor
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'll find cheap prices from €301 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?

  1. Choose your travel dates: The things you plan to do in Windsor and your preferred season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.