Windsor Holidays from £305

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Your Windsor Holiday

When a city stay is calling, answer it with a Windsor holiday package. With all your travel needs in place before you leave, all you have to do here is concentrate on having fun. Every trip to Windsor should include a little sightseeing. le Parc Historique de la Poudriere de Windsor is a superb place to kick off your exploring. Your Windsor holiday is just a few clicks away. Browse airfares, hotels and more on Expedia for a trip that's tailored to suit your travel style.

The Latest Windsor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
EXE Domus Aurea

EXE Domus Aurea

3 out of 5
Rome City Centre
per person
31 Aug - 5 Sept
found 1 day ago
Return flight included
London (LGW) to Rome (FCO)
8/10 Very Good! (476 reviews)
Good location and friendly staff. Although this didn’t bother me, it could be a bit noisy at night due to some night walkers on the street.

Reviewed on 19 Nov 2024

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
per person
15 Sept - 21 Sept
found 7 hours ago
Return flight included
London (LGW) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Everything was amazing- The accommodations, the property decor, the staff like Adrian and Chef Luis were very personable and welcoming. Our room was upgraded from partial ocean view to full as we were celebrating our 23rd wedding anniversary, so that was a nice touch. We would definitely book again.

Reviewed on 31 May 2025

Relais de la Poste

Relais de la Poste

3 out of 5
Rome City Centre
per person
18 Sept - 21 Sept
found 2 days ago
Return flight included
London (LGW) to Rome (FCO)
9.2/10 Wonderful! (527 reviews)
We had a very good stay here! The hotel staff were incredibly friendly and helpful with everything. The hotel's location is great and surrounded by a bunch of shopping destinations. The room itself was nice, but a bit small. We thought we paid for a slightly bigger room than we got, so the size of the room was a bit surprising at first. Also, we did get our room cleaned but they did not give us towels or clean certain areas. However, our stay here was mostly positive and we would recommend staying here! Its a great location.

Reviewed on 22 Jun 2025

Màs Boutique Hotel

Màs Boutique Hotel

3 out of 5
Rome City Centre
per person
14 Sept - 19 Sept
found 1 day ago
Return flight included
London (LGW) to Rome (FCO)
9.4/10 Exceptional! (29 reviews)
Very clean and safe hotel with spacious rooms, despite the hotel itself being old and compact with a limited number of rooms. The staff is very nice, and the area is beautiful, lively, and fun.

Reviewed on 15 Jun 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
6 Aug - 14 Aug
found 1 day ago
Return flight included
London (LGW) to New York (JFK)
9.8/10 Exceptional! (1,212 reviews)
Very neat hotel! Great to stay at travel!

Reviewed on 23 Jun 2025

Oceana Santa Monica, LXR Hotels & Resorts

Oceana Santa Monica, LXR Hotels & Resorts

5 out of 5
Wilshire Montana
per person
1 Aug - 8 Aug
found 1 day ago
Return flight included
London (LON) to Los Angeles (LAX)
9.2/10 Wonderful! (456 reviews)
Very nice location and clean properties

Reviewed on 16 Aug 2024

Windsor Essential Information

Language
English
Currency
Canadian dollars
Population
5,400
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC
Top Sights
Centre dInterpretation de lArdoise, Centre dInterprétation de lHistoire de Sherbrooke and Sherbrooke Golf Club

Our pick of the best Windsor Hotel Deals

OTL Gouverneur Sherbrooke
OTL Gouverneur Sherbrooke
5 out of 5
3131 rue King Ouest, Sherbrooke, QC
Stay at this 5-star luxury hotel in Sherbrooke. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
9.6/10 Exceptional! (1,540 reviews)
"Amazing stay and great breakfast"

Reviewed on 22 Jun 2025

OTL Gouverneur Sherbrooke
Manoir des Sables Hôtel & Golf
Manoir des Sables Hôtel & Golf
4 out of 5
90 Des Jardins Ave., Orford, QC
Stay at this 4-star spa hotel in Orford. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms in their ...
8.2/10 Very Good! (1,007 reviews)
"We liked everything very much, the hotel and entertainment are thought out for any weather, the room is comfortable, everything was super that we even decided to extend our stay for 1 day"

Reviewed on 20 Jun 2025

Manoir des Sables Hôtel & Golf
Grand Times Hotel Sherbrooke
Grand Times Hotel Sherbrooke
4 out of 5
1, rue Belvedere Sud, Sherbrooke, QC
Stay at this 4-star business-friendly hotel in Sherbrooke. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,002 reviews)
"Location near the Lac du Nations, cleanliness, quiet, artwork, everything seemed new."

Reviewed on 5 Jun 2025

Grand Times Hotel Sherbrooke
See all 169 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Windsor travel package cost?
Starting from just £305, a package is your passport to inexpensive travel. Custom build your Windsor escape by choosing from our extensive range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Windsor travel package?
Don't stress if you're rethinking your Windsor travel package --- it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We realise your circumstances can suddenly change, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to Windsor?
Secure flights that fit in with your schedule, add a hotel to your booking and see how much you save with a Windsor holiday package. It's as easy as that! From flights and hotels to rental cars and activities, Expedia makes travelling on a budget easy. And with more than 550 partner airlines and 1,000,000 properties throughout the world to select from, you won't be short of choice.
Does Expedia offer Book Now, Pay Later Windsor holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has worked out a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book an incredible getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying a little each month works for you, choose this option at checkout.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Windsor?
There's lots to explore in Windsor, so spend your nights close to its top sights and maximize your time sightseeing. Le Parc Historique de la Poudriere de Windsor is one spot to add to your must-see list.
What are the top hotels in Windsor?
Reserve a room at Hotel Zero 1. It's one of the neighbourhood's most in-demand hotels. Another top option in Windsor is Le Chabrol Hotel & Suites.
How far in advance should I book my Windsor holiday?
Browse Expedia to compare international fares as soon as you know your travel dates. You can generally purchase a ticket up to a year before departure. If you can't find your preferred air carrier, or you're booking late, don't worry. Cheap fares to Windsor sometimes emerge within weeks of the date of departure.
What does an Expedia Windsor travel package include?
Packages include rental cars, hotels and flights, but you can mix and match them to create your ideal Windsor holiday. You can also add on a few activities and experiences once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score deals you won't find anywhere else.
What should I know before booking a Windsor travel package?
Booking all the parts of your trip together is one of the best ways to save. Bundle your car rentals, flights and hotels into a neat little package. But your options don't end at hotels. Expedia offers all kinds of properties, including holiday rentals like mountain cabins and serviced residences. You've got choices galore!
Can I choose my airline with a Windsor Expedia travel package?
With a travel package, you're always in charge. Whether you'd like to fly to Windsor in first class or coach, simply select from the available airline options. Expedia has access to over 550 airline partners throughout the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.