Winkler Vacation Packages

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Your Winkler Vacation

Book a Winkler vacation package and prepare for a fantastic adventure. Well known for its welcoming locals and diversity, there's plenty to love about this interesting city. A trip to Winkler is a superb opportunity to do a bit of sightseeing. Check out renowned attractions like Winkler Aquatic Centre, Bethel Heritage Park and Winkler Golf Club. Whoever you're going away with and whether your budget is big or small, your ultimate Winkler vacation is just a few clicks away with Expedia.

Top Winkler Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Canad Inns Destination Centre Garden City

Canad Inns Destination Centre Garden City

3 out of 5
Leila-McPhillips Triangle
Price was CA $508, price is now CA $414 per person
CA $414
per person
Aug 13 - Aug 16
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Winnipeg (YWG)
8/10 Very good! (1,013 reviews)
Hotel was nice and rooms were clean. The pool area was nice as well. The slide was a nice addition and the water mushroom for the kids section was super cute.

Reviewed on Jun 29, 2026

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
Price was CA $614, price is now CA $463 per person
CA $463
per person
Aug 13 - Aug 16
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Winnipeg (YWG)
9/10 Wonderful! (1,679 reviews)
Room was clean, check in and out easy and quick. Food was good in restaurant.

Reviewed on Jun 29, 2026

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was CA $589, price is now CA $451 per person
CA $451
per person
Aug 13 - Aug 16
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Winnipeg (YWG)
8.4/10 Very good! (1,641 reviews)
Great location!

Reviewed on Jun 28, 2026

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was CA $564, price is now CA $454 per person
CA $454
per person
Aug 13 - Aug 16
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Winnipeg (YWG)
8.4/10 Very good! (1,003 reviews)
I stayed here for a solo trip. Check-in and check-out were smooth, but I had to wait for housekeeping to check my room before I could get my deposit refunded. That was a little annoying. The property has a tavern, so be prepared for intoxicated people sharing your floor, however, they were mostly well-behaved during my stay.

Reviewed on Jun 29, 2026

Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was CA $617, price is now CA $509 per person
CA $509
per person
Aug 13 - Aug 16
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Winnipeg (YWG)
8.4/10 Very good! (3,101 reviews)
Room was not cleaned when I asked several times

Reviewed on Jun 30, 2026

Ready to book your vacation to Winkler?

 

Choose your dates

Winkler Hotel Deals

Days Inn & Suites by Wyndham Winkler

Days Inn & Suites by Wyndham Winkler

2.5 out of 5
395 Boundary Trail Winkler MB
The price is CA $140 per night from Jul 5 to Jul 6
CA $140
CA $156 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (739 reviews)
"Clean rooms, friendly staff, and great amenities. The Breakfast was a nice touch. Eggs, bacon, waffles, yogurt, oatmeal, bagels, muffins. Yum!"

Reviewed on Jun 28, 2026

Days Inn & Suites by Wyndham Winkler
Best Western Plus Winkler

Best Western Plus Winkler

2.5 out of 5
1705 Diamond Dr Winkler MB
The price is CA $166 per night from Jul 19 to Jul 20
CA $166
CA $186 total
Jul 19 - Jul 20
includes taxes & fees
9.4/10 Exceptional! (358 reviews)
"Very good Breakfast"

Reviewed on Jun 29, 2026

Best Western Plus Winkler
Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
851 Main Street Winkler MB
Get rates
Quality Inn & Suites
See all 12 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Winkler attractions

Winkler Aquatic Centre

8.6/10 (14 reviews)
Bring your family to Winkler Aquatic Centre and enjoy the excitement of this amusement park in Winkler. Discover the stargazing spots while you're in the area.
See properties

Frequently asked questions

How much does a Winkler vacation package cost?
You'll find cheap prices from CA $414 on Expedia for your Winkler break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Winkler costs.
What are the cheapest months to go to Winkler?
If you're looking to score a cheap Winkler vacation package, consider planning a trip in January, May and November. You'll typically find better rates on hotels and airfares during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Winkler?
Generally, a handful of days is enough to visit the top sights during your Winkler vacation. But if you want to have more time to relax or take day trips, think about extending your trip.
Is it worth booking a vacation package to Winkler?
Well known for its festivals, culture and plenty of other highlights, you can be assured Winkler is a good vacation destination. Some of the most popular attractions to stick on your to-do list? Check out Winkler Aquatic Centre and PW Enns Centennial Concert Hall during your Winkler vacation.
How to find the best Winkler package deals?
Bagging a cheap Winkler package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most economical Winkler package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winkler vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Winkler vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Winkler?
If you're considering a spontaneous Winkler trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Winkler?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Winkler.
  2. Plan your budget wisely: In addition to the price of your hotel, you should factor in other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that may come up during your trip to Winkler.
  3. Decide how long to go for: Now that you're more familiar with Winkler, you can figure out the ideal length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the perfect Winkler vacation package for you.

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