Winkler Holidays

    deals illustration
    Better together
    Save up to S$134 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Winkler

Days Inn & Suites by Wyndham Winkler
Days Inn & Suites by Wyndham Winkler
2.5 out of 5
395 Boundary Trail, Winkler, MB
Fully refundableReserve now, pay when you stay
The price is S$127 per night from 3 Aug to 4 Aug
S$127
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (510 reviews)
"Good value"

Reviewed on 6 Jul, 2025

Days Inn & Suites by Wyndham Winkler
Best Western Plus Winkler
Best Western Plus Winkler
2.5 out of 5
1705 Diamond Dr, Winkler, MB
Fully refundableReserve now, pay when you stay
The price is S$131 per night from 3 Aug to 4 Aug
S$131
3 Aug - 4 Aug
includes taxes & fees
9.4/10 Exceptional! (265 reviews)
"The hotel is great. We are loving the pool. Our dog is even enjoying the hotel. They gave us a nice room near the back door so we could take her out to go to the bathroom easy. We really like the town of Winkler. Janzens Paint is a really cool store with lots of games and hobby stuff, the kids loved ..."

Reviewed on 29 Jun, 2025

Best Western Plus Winkler
Quality Inn & Suites
Quality Inn & Suites
2.5 out of 5
851 Main Street, Winkler, MB
8.8/10 Excellent! (317 reviews)
"Always a good place sad its gone"

Reviewed on 2 May, 2025

Get rates
Quality Inn & Suites
See all 14 properties in Winkler
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 Winkler holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday to Winkler costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Winkler?
If you're hoping to book a cheap Winkler holiday package, consider planning a trip in January, May and November. You'll typically find better rates on hotels and flights during these quieter months --- ideal for budget-conscious travellers.
How many days is enough for Winkler?
Typically, a handful of days is enough to check out the main attractions during your Winkler holiday. But if you'd like to have some time to unwind or go on day trips, consider extending your itinerary.
Is it worth booking a holiday package to Winkler?
Whether you're planning to visit attractions such as Winkler Aquatic Centre and PW Enns Centennial Concert Hall, or want to experience its terrific festivals and culture, a Winkler holiday will leave you with lasting memories. Book your trip with Expedia and find out why Winkler is such a good holiday destination.
How to find the best Winkler package deals?
Use Expedia's filters to find some terrific Winkler package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Winkler package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Winkler holiday as a package?
You can enjoy significant savings on your Winkler escape by booking a customised holiday package. Check the "Package" heading, then enter your travel dates and destination to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Winkler?
If you've got your Winkler travel dates finalized, book as early as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Winkler?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Winkler.
  2. Set your budget: Factor in costs such as flights, food and transportation when calculating how much to save for your trip to Winkler. Then, choose a property that matches your budget, whether that's a low-cost option or a more upscale getaway.
  3. Determine how many days away: Start by making a list of all the activities and sights you'd like to experience in Winkler. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your accommodation and airfare: After you've nailed down your travel dates and duration, book the ideal Winkler holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.