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
per person
Oct 5 - Oct 10
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very Good! (1,013 reviews)
, I liked that the place was kid friendly.

Reviewed on Aug. 2, 2025

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
9/10 Wonderful! (1,241 reviews)
Staff was rude, uninformed, and the restaurant food was about worse I have ever eaten. Sorry, had potential but came up short.

Reviewed on Aug. 2, 2025

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
per person
Oct 5 - Oct 10
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.2/10 Very Good! (1,000 reviews)
Easy exit out of city

Reviewed on Aug. 4, 2025

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
per person
Oct 5 - Oct 10
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very Good! (1,032 reviews)
Restauriert was excellent for breakfast. Dinner service was good. Kitchen slow

Reviewed on Aug. 2, 2025

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
per person
Oct 5 - Oct 10
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
7.6/10 Good! (1,004 reviews)
Nice room Good shower Check in quick

Reviewed on Jul. 20, 2025

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 $134 per night from Aug 7 to Aug 8
CA $134
CA $150 total
Aug 7 - Aug 8
includes taxes & fees
8.8/10 Excellent! (526 reviews)
"It was great experience."

Reviewed on Jul. 25, 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
The price is CA $125 per night from Aug 31 to Sep 1
CA $125
CA $140 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (273 reviews)
"Very nice stay"

Reviewed on Aug. 2, 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 May 2, 2025

Get rates
Quality Inn & Suites
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

Discover the most popular places to visit in Winkler

Bethel Heritage Park

Explore the great outdoors at Bethel Heritage Park, a lovely green space in Winkler. Discover the stargazing spots while you're in the area.

Bethel Heritage Park

Winkler Aquatic Centre

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.

Winkler Aquatic Centre

PW Enns Centennial Concert Hall

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.

PW Enns Centennial Concert Hall

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.

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