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.
Sandman Hotel & Suites Winnipeg Airport

Sandman Hotel & Suites Winnipeg Airport

3 out of 5
St. James
Price was CA $434, price is now CA $359 per person
CA $359
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.2/10 Very Good! (1,279 reviews)
Was a great place to stay! Thank you..

Reviewed on Aug. 28, 2025

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
Price was CA $801, price is now CA $646 per person
CA $646
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Winnipeg (YWG)
9/10 Wonderful! (1,263 reviews)
Convenient and clean

Reviewed on Aug. 29, 2025

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was CA $794, price is now CA $643 per person
CA $643
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Winnipeg (YWG)
7.8/10 Good! (1,059 reviews)
Very quiet. Appreciated that a keycard was required to get to our floor. Added an extra level of security.

Reviewed on Aug. 29, 2025

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was CA $755, price is now CA $619 per person
CA $619
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Winnipeg (YWG)
8.2/10 Very Good! (1,013 reviews)
What a joy this place is. Would definitely stay here again. Staff is amazing, polite, friendly, helpful. Inn is clean, organized, quiet. Pool was amazing. They even were able to check us in early even though we would have been happy to wait till it was time.

Reviewed on Aug. 28, 2025

Canad Inns Destination Centre Garden City

Canad Inns Destination Centre Garden City

3 out of 5
Leila-McPhillips Triangle
Price was CA $738, price is now CA $609 per person
CA $609
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Winnipeg (YWG)
8/10 Very Good! (1,011 reviews)
The bath room down grades due to poo caulking condition.

Reviewed on Aug. 30, 2025

Ready to book your vacation to Winkler?

 

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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 $124 per night from Sep 7 to Sep 8
CA $124
CA $139 total
Sep 7 - Sep 8
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 $132 per night from Sep 21 to Sep 22
CA $132
CA $148 total
Sep 21 - Sep 22
includes taxes & fees
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 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.