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 $605, price is now CA $487 per person
CA $487
per person
Feb 4 - Feb 7
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.2/10 Very good! (1,005 reviews)

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was CA $663, price is now CA $519 per person
CA $519
per person
Feb 4 - Feb 7
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very good! (1,004 reviews)

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was CA $727, price is now CA $580 per person
CA $580
per person
Feb 4 - Feb 7
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very good! (1,756 reviews)
Stayed here while traveling for business. Location is good for downtown trips, but hotel is dated and room had a mild, musty smell, but was clean. Air conditioning in room was loud while on. Breakfast buffet was good enough. Staff was very friendly. Overall, I would stay here again when traveling for work.

Reviewed on Nov 13, 2026

Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was CA $685, price is now CA $564 per person
CA $564
per person
Feb 4 - Feb 7
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very good! (3,298 reviews)

Country Inn & Suites by Radisson, Winnipeg, MB

Country Inn & Suites by Radisson, Winnipeg, MB

2.5 out of 5
St. James
Price was CA $720, price is now CA $596 per person
CA $596
per person
Feb 4 - Feb 7
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
7.6/10 Good! (1,002 reviews)

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
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Dec 13 to Dec 14
CA $123
CA $138 total
Dec 13 - Dec 14
includes taxes & fees
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 CA $149 per night from Dec 6 to Dec 7
CA $149
CA $167 total
Dec 6 - Dec 7
includes taxes & fees
9.4/10 Exceptional! (400 reviews)
"This was the 2nd time I stayed here. The staff was very friendly and courteous. Rooms were clean and quiet. Breakfast was delicious. Would recommend 👌"

Reviewed on Nov 5, 2026

Best Western Plus Winkler
Studio 7 – Mighty, Modern, Fully Equipped

Studio 7 – Mighty, Modern, Fully Equipped

Winkler MB
The price is CA $99 per night from Nov 22 to Nov 23
CA $99
CA $131 total
Nov 22 - Nov 23
includes taxes & fees
8.8/10 Excellent! (5 reviews)
"It was a nice little spot. Best suited for 1 person. However, not designed for short people. (5'3") Had to stand on tip toes to see my entire face in the mirror. And dishes in kitchenette were difficult to reach due to high shelving."

Reviewed on Oct 12, 2026

Studio 7 – Mighty, Modern, Fully Equipped
See all 13 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

PW Enns Centennial Concert Hall

6.4/10 (5 reviews)
You can enjoy a show at PW Enns Centennial Concert Hall during your trip to 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 $487 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.