Winner Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Winner vacation deals
Price found within the past 48 hours. Click for updated prices.
- Falko Hotel
Sept 4 - Sept 8Falko Hotel + Flight
Meise3 nights4.0 star property8.6/10 - Excellent (46 reviews)"The staff was very courteous and friendly. However, the room we were assigned on the first night was quite a shock. The shower was located in the bedroom with only a single glass wall for separation. There was no sofa and only one chair in the room, as well as just one small bath towel provided. Overall, the room felt more like a closet than a proper hotel room. Given the price we paid, we expected a much more decent accommodation. The following day, I requested a different room, which we..."Reviewed December 17, 2025Roundtrip • Montreal (YMQ) - Brussels (BRU)YUL - BRU • Nonstop BRU - YUL • 1 stopCA $1,115CA $935found 1 day agoper traveller - Monsieur Ernest
Sept 7 - Sept 12Monsieur Ernest + Flight
Historical Center Bruges4 nights3.0 star property9.0/10 - Wonderful (504 reviews)"We had a wonderful stay - the hotel is in a quiet location but only a few minutes walk from lots of shops, restaurants and cafes. The hotel itself has friendly, helpful staff and a lovely courtyard garden for coffee in the morning or a drink in the evening. Rooms have everything you need and a comfortable bed. Would return and highly recommend to others!"Reviewed July 5, 2026Roundtrip • Montreal (YMQ) - Brussels (BRU)YUL - BRU • Nonstop BRU - YUL • NonstopCA $1,672CA $1,267found 1 day agoper traveller - A Place - Boutique Hotel Emile
Sept 10 - Sept 15A Place - Boutique Hotel Emile + Flight
South Antwerp4 nights3.0 star property9.8/10 - Exceptional (72 reviews)"A beautiful, small hotel in the quiet south of Antwerp that felt like a luxurious escape during traveling. The rooms are so cozy and well stocked with amenities and thoughtful touches that did not go missed. The staff is truly outstanding in their hospitality, support, friendliness, and knowledge. Truly a great, memorable experience all around. "Reviewed December 5, 2025Roundtrip • Montreal (YUL) - Brussels (BRU)YUL - BRU • Nonstop BRU - YUL • NonstopCA $1,422CA $1,131found 1 day agoper traveller - The Augustin
Sept 20 - Sept 26The Augustin + Flight
Lower Town5 nights4.0 star property8.4/10 - Very good (1,002 reviews)"For the price, this hotel was very disappointing. The advertises a top-rated breakfast, but in our experience it wasn’t even worth €5. The scrambled eggs were contaminated with pork juices because the same serving spoon was used for both the eggs and the bacon. In a country like Belgium, where halal options are widely available, I expected better attention to avoiding cross-contamination. The amenities were poor. There was no YouTube or Netflix on the TV, and when I mentioned it at reception,..."Reviewed July 14, 2026Roundtrip • Toronto (YTO) - Brussels (BRU)YYZ - BRU • 1 stop BRU - YYZ • 1 stopCA $1,913CA $1,600found 1 day agoper traveller - Hotel de Orangerie by CW Hotel Collection - Small Luxury Hotels of the World
Sept 7 - Sept 12Hotel de Orangerie by CW Hotel Collection - Small Luxury Hotels of the World + Flight
Historical Center Bruges4 nights4.0 star property9.6/10 - Exceptional (1,001 reviews)Roundtrip • Montreal (YMQ) - Brussels (BRU)YUL - BRU • Nonstop BRU - YUL • NonstopCA $2,213CA $1,881found 1 day agoper traveller
Winner Hotel Deals
9.2 out of 10, Wonderful, (51 reviews)
9.2/10
Wonderful
(51 reviews)
The price is CA $192
CA $192
CA $215 total
includes taxes & fees
Sep 1 - Sep 2
9.2 out of 10, Wonderful, (218 reviews)
9.2/10
Wonderful
(218 reviews)
"Hotel was quiet and peaceful. Just what I wanted. Breakfast was good and my room was cleaned daily."
The price is CA $195
CA $195
CA $218 total
includes taxes & fees
Aug 13 - Aug 14
8.6 out of 10, Excellent, (95 reviews)
8.6/10
Excellent
(95 reviews)
"All good. Bed was quite small, breakfast was a little basic. Ideal for a overnight work stay though. Nice and close to town centre."
The price is CA $228
CA $228
CA $256 total
includes taxes & fees
Aug 16 - Aug 17
Hotel De Vossemeren by Center Parcs
Hotel De Vossemeren by Center Parcs3.5 star property
10.9 km from Winner
8.2 out of 10, Very good, (53 reviews)
8.2/10
Very good
(53 reviews)
"Was difficult to locate hotel. Excellent breakfast"
The price is CA $182
CA $182
CA $204 total
includes taxes & fees
Aug 30 - Aug 31
7.0 out of 10, Good, (33 reviews)
7.0/10
Good
(33 reviews)
"The reception staff was terrible, I parked in the underground carpark and all the reception staff cared about was the 12euro payment. after paying i didn't get a recpite as I personally had no VAT number. When i asked where my room was the answer i got was "round there""
The price is CA $243
CA $243
CA $273 total
includes taxes & fees
Aug 16 - Aug 17
7.6 out of 10, Good, (10 reviews)
7.6/10
Good
(10 reviews)
The price is CA $154
CA $154
CA $209 total
includes taxes & fees
Aug 20 - Aug 21
De Watermolen
De Watermolen11.6 km from Winner
8.2 out of 10, Very good, (43 reviews)
8.2/10
Very good
(43 reviews)
The price is CA $291
CA $291
CA $326 total
includes taxes & fees
Aug 2 - Aug 3
9.0 out of 10, Wonderful, (117 reviews)
9.0/10
Wonderful
(117 reviews)
The price is CA $195
CA $195
CA $218 total
includes taxes & fees
Aug 11 - Aug 12
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.
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 Winner vacation package cost?
You can pick up a vacation package to this popular destination from CA $935 on Expedia. But how much your vacation to Winner costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Winner?
If you'd like to score a cheap Winner vacation package, consider visiting in January, February and March. You'll generally find lower rates on flights and hotels during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Winner?
With a well-organized itinerary, you can easily tick off the top Winner attractions in a few days. But if you want to discover lesser-known spots or take day trips, consider booking your Winner vacation for longer.
How to find the best Winner package deals?
Begin your search for a Winner package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Winner package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winner escape underway.
Is it cheaper to book a Winner vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can customize your Winner escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Winner?
Land incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Winner adventure.
How to plan a trip to Winner?
- Pick your travel dates: The things you plan to do in Winner and your preferred season can help you decide when to go.
- Budget wisely: As well as the cost of your stay, you should consider other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Winner.
- Work out your trip length: Think about how long you want to spend exploring Winner. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored Winner vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.