Winkler Vacations from $1,019

A Winkler vacation package lets you combine round-trip flights, hotel stays, and rental cars. Many hotels in Winkler offer free breakfast, a convenient perk for travelers. You can also often add an airport shuttle service to your package, especially useful when flying into Winnipeg James Armstrong Richardson International Airport (YWG).


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

When you bundle, you can save up to 30%*. To save money on a Winkler package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

For families, a Winkler vacation package built around a stay at Best Western Plus Winkler (rated 9.4 out of 10) is a strong choice. This hotel, about 1 mile from central Winkler, offers an indoor pool and kitchenettes, with travelers often praising the great rooms and overall well-maintained facilities.


Couples or general travelers looking for a comfortable stay might consider a Winkler vacation package including Days Inn & Suites by Wyndham Winkler, rated 8.7 out of 10. Located about a 10-minute walk from central Winkler, it features an indoor pool, hot tub, and a bar/lounge, and travelers frequently highlight the clean pool and kind staff.

Winkler is primarily an urban and family-friendly destination, offering a blend of recreational activities and local culture. The city's heritage is showcased at Bethel Heritage Park, about a 5-minute walk from central Winkler, which explains the area's Mennonite settlement history.


For cultural immersion, you can visit the Pembina Thresherman's Museum, which showcases historical buildings and agricultural items, or enjoy performances at the PW Enns Centennial Concert Hall, about a 10-minute walk from the city center. The Winkler Arts and Culture Centre also organizes local art programming. The city hosts events like the Harvest Festival in mid-August and Canada Day celebrations on July 1, making a Winkler vacation package a good choice for those interested in community events and local heritage.

A Winkler vacation offers a variety of activities, from exploring local history to enjoying recreational facilities:


Browse and book things to do in Winkler on Expedia.

For a Winkler vacation package, a rental car offers the most flexibility, especially if you plan to explore beyond the city limits. Winkler is well-connected to other communities via its highway system, including a 4-lane divided highway to Morden. However, within the city, an on-demand transit service was launched in 2024, providing shuttle service within city limits, and local taxis are also available.


If your Winkler vacation packages with flights include arrival at Winnipeg James Armstrong Richardson International Airport (YWG), which is about 59 miles away, a rental car or pre-arranged shuttle would be necessary for the journey to Winkler.

Winkler vacation package hotels are generally conveniently located, with options close to the city center and its attractions. For example, Days Inn & Suites by Wyndham Winkler, rated 8.7 out of 10, is about a 10-minute walk from central Winkler. The Best Western Plus Winkler, rated 9.4 out of 10, is also well-situated about 1 mile from the city's heart.


These central locations make it easy to access local sights and amenities during your stay.

Winkler vacation package hotels in the city center often place you within walking distance of local amenities. For instance, Days Inn & Suites by Wyndham Winkler, rated 8.7 out of 10, is about a 10-minute walk from central Winkler, where you'll find various shops and dining options. Travelers often praise the spotless rooms and clean pool at this hotel. The Best Western Plus Winkler, rated 9.4 out of 10, is also conveniently located about 1 mile from central Winkler, with guests frequently highlighting its great location and good breakfast.


These hotels offer easy access to nearby attractions like Bethel Heritage Park and Valley Bowling Lanes, both about a 5-minute walk from the city center, making it simple to explore on foot.

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Winkler vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

To find last-minute vacation packages to Winkler, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Free cancellation on a Winkler vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Winkler getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.