Windsor Holidays

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    Save up to €900 when you book a flight and hotel together*

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Top Flight + Hotel Deals in Windsor

Price found within the past 48 hours. Click for updated prices.
Hotel Delle Civette

Hotel Delle Civette

3 out of 5
Nomentano
Save 100% on your flight
Price was €652, price is now €346 per person
€346
per person
17 Aug - 21 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Rome (FCO)
9.6/10 Exceptional! (312 reviews)
Excellent breakfast, and staff. Air conditioning was kind of hot.

Reviewed on 5 Jul 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €2,446, price is now €1,444 per person
€1,444
per person
16 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
Line up for elevators Had to walk down 15 flights after waiting for over 15 minutes . Sheets worn out and not comfortable

Reviewed on 15 Jul 2026

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,884, price is now €1,115 per person
€1,115
per person
16 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8/10 Very good! (2,471 reviews)
Great location!

Reviewed on 15 Jul 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €2,370, price is now €1,406 per person
€1,406
per person
16 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
This place is clean and new. Location is perfect. We would return.

Reviewed on 15 Jul 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,294, price is now €796 per person
€796
per person
10 Sept - 14 Sept
found 7 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
i dont want to write anything but its forcing me to. Everything was fine.

Reviewed on 15 Jul 2026

Top hotels in Windsor

Manoir Des Sables, an Ascend Collection Hotel

Manoir Des Sables, an Ascend Collection Hotel

4 out of 5
90 Des Jardins Ave. Orford QC
Fully refundableReserve now, pay when you stay
The price is €103 per night from 9 Aug to 10 Aug
€103
9 Aug - 10 Aug
includes taxes & fees
8.4/10 Very good! (1,324 reviews)
"It was quite clean and enjoyed the hot tub and sauna,friendly staff!"

Reviewed on 15 Jul 2026

Manoir Des Sables, an Ascend Collection Hotel
Hotel Cheribourg, an Ascend Collection Hotel

Hotel Cheribourg, an Ascend Collection Hotel

4 out of 5
2603 Chemin Du Parc Orford QC
Fully refundableReserve now, pay when you stay
The price is €93 per night from 26 Jul to 27 Jul
€93
26 Jul - 27 Jul
includes taxes & fees
8.2/10 Very good! (1,231 reviews)
"Correct"

Reviewed on 15 Jul 2026

Hotel Cheribourg, an Ascend Collection Hotel
Comfort Inn Sherbrooke - Estrie

Comfort Inn Sherbrooke - Estrie

2.5 out of 5
4295 boul. Bourque Sherbrooke QC
Fully refundableReserve now, pay when you stay
The price is €101 per night from 19 Jul to 20 Jul
€101
19 Jul - 20 Jul
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
"Essayer d’enlever les tapis qui sentent beaucoup l’humidité, l’air climatisé est très bruyant,le déjeuner était correct sans plus. Nous avons été très bien accueilli, le stationnement est super pour les chambres au bas surtout"

Reviewed on 12 Jul 2026

Comfort Inn Sherbrooke - Estrie
See all 189 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.

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.
See properties

Frequently asked questions

How much does a Windsor holiday package cost?
You'll find cheap prices from €346 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.