Winkler Vacations from $369

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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.

The Latest Winkler vacation packages

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

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $471, price is now $369 per person
$369
per person
Oct 24 - Oct 27
found 22 hours ago
Roundtrip flight included
New York (NYC) to Winnipeg (YWG)
8.2/10 Very Good! (1,010 reviews)
I like the location and convenience to the shopping mall, casino and dining. There’s also a GT if you need to do some quick shopping or just little things like water and snacks.

Reviewed on Aug 18, 2025

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $513, price is now $389 per person
$389
per person
Oct 24 - Oct 27
found 22 hours ago
Roundtrip flight included
New York (NYC) to Winnipeg (YWG)
8.2/10 Very Good! (1,289 reviews)
Great location and the staff was friendly, and the breakfast was very good.

Reviewed on Aug 20, 2025

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $476, price is now $373 per person
$373
per person
Oct 24 - Oct 27
found 22 hours ago
Roundtrip flight included
New York (NYC) to Winnipeg (YWG)
8/10 Very Good! (1,042 reviews)
Its in great but did notice how the outside was so dirty ,pop cans , cigarette butts etc

Reviewed on Aug 19, 2025

Inn At The Forks

Inn At The Forks

3.5 out of 5
Downtown Winnipeg
Price was $833, price is now $673 per person
$673
per person
Oct 24 - Oct 27
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Winnipeg (YWG)
9/10 Wonderful! (1,001 reviews)
Situated in the historic Forks - the hotel was excellent, new and lots of great walking areas right outside. We easily parked in the parkade with our truck, and when we were ready for supper we ate at The Old Spahggitti Factory (also excellent) next door. I would stay here again.

Reviewed on Aug 18, 2025

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
Price was $570, price is now $476 per person
$476
per person
Oct 24 - Oct 27
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Winnipeg (YWG)
9/10 Wonderful! (1,250 reviews)
Check in staff was nice and kind but the room was smelly when I went in. The hair dryer was old(seemed dangerous) and too noisy.

Reviewed on Aug 20, 2025

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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

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
$90 nightly
The price is $100 total per night from Sep 7 to Sep 8
$100 total
Sep 7 - Sep 8
Total includes taxes and fees
8.8/10 Excellent! (537 reviews)
"Everything is beautiful here :)"

Reviewed on Aug 19, 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
$94 nightly
The price is $106 total per night from Sep 14 to Sep 15
$106 total
Sep 14 - Sep 15
Total includes taxes and fees
9.4/10 Exceptional! (280 reviews)
"Stay was quite nice, although there are a few things worth noting. We were in a suite capable of sleeping 6 people, there were only 2 bath towels, no flat sheet for the convertible bed, there was one small bar of soap for the sink and shower and the smallest bottle of shampoo. Staff was super helpful ..."

Reviewed on Aug 19, 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.

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Frequently asked questions

How much does a Winkler vacation package cost?
You can pick up a vacation package to this destination from $369 on Expedia. But how much your vacation 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?
December, January and February are the best times to look for cheap Winkler vacation packages. Choosing to travel in less busy months means you'll typically find reduced prices on flights and accommodations.
How many days is enough for Winkler?
With a well-planned itinerary, you can easily visit the most popular Winkler sights in a few days. But if you want to discover hidden gems or take day trips, think about booking your Winkler vacation for longer.
Is it worth booking a vacation package to Winkler?
Known for its festivals, culture and plenty of other highlights, you can be certain Winkler is a good vacation destination. Some of the top attractions to put on your to-do list? Check out Winkler Aquatic Centre and Meadow's Golf and Amusement Park during your Winkler vacation.
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 vacation package well in advance.
Is it cheaper to book a Winkler vacation as a package?
You can enjoy significant savings on your Winkler escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to view some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Winkler vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Winkler trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.