Headingley Vacation Packages
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Your Headingley Vacation
When a getaway to the city is calling, answer it with a vacation package to Headingley. The neighborhood of Downtown Winnipeg, which is great for markets, cafes and bars and pubs, makes a fantastic base for your adventures. Fill your itinerary with visits to Assiniboia Downs, BellMTS Iceplex and Unicity Mall, some of the attractions you just have to see during a trip to Headingley. Don't delay visiting this city any longer. The perfect Headingley vacation is a couple of clicks away with Expedia.
Top Headingley Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
Downtown Winnipeg
Price was CA $600, price is now CA $552 per person
CA $552
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
9.2/10 Wonderful! (1,072 reviews)
The charm of the Garry is historic and fabulous. Staff are very attentive. Location in great.
Reviewed on Mar 8, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
St. James
Price was CA $803, price is now CA $642 per person
CA $642
per person
Apr 21 - Apr 25
found 1 hour ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very Good! (2,832 reviews)
Just needs a shower in the pool area unless I missed it. Overall, it was okay however, there were children knocking on room doors and running off. Thanks to front desk for responding to this.
Reviewed on Mar 11, 2026
Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
Price was CA $2,060, price is now CA $1,741 per person
CA $1,741
per person
Apr 19 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTZ) to Winnipeg (YWG)
9/10 Wonderful! (1,578 reviews)
It was nice, the staff were very helpful and friendly.
I will definitely be back.
Reviewed on Mar 11, 2026
The Fairmont Winnipeg Gold Experience
Exchange District
Price was CA $811, price is now CA $728 per person
CA $728
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very Good! (33 reviews)
Enjoyed the Fairmont Gold Experience. Gold Lounge was closed for renovations on our last day, but the hotel took great care of us in the restaurant for breakfast. We will be back.
Reviewed on Feb 5, 2025
Headingley Hotel Deals
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Mar 25 to Mar 26
CA $184
CA $206 total
Mar 25 - Mar 26
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
Easy access for a late might stop. Friendly staff, nice room and a decent breakfast.
Reviewed on Mar 8, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Mar 13 to Mar 14
CA $179
CA $212 total
Mar 13 - Mar 14
includes taxes & fees
8.4/10 Very Good! (2,855 reviews)
Just needs a shower in the pool area unless I missed it. Overall, it was okay however, there were children knocking on room doors and running off. Thanks to front desk for responding to this.
Reviewed on Mar 11, 2026
The Grand Winnipeg Airport Hotel by Lakeview
1979 Wellington Ave. Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Mar 21 to Mar 22
CA $137
CA $163 total
Mar 21 - Mar 22
includes taxes & fees
9.2/10 Wonderful! (1,359 reviews)
The room was great - comfortable and clean. Check in was easy.
Reviewed on Mar 8, 2026
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.
Discover the most popular places to visit in Headingley
Thunder Rapids Fun Park
Bring the kiddos to Thunder Rapids Fun Park and enjoy some excitement at this theme park in Headingley. Stroll along the riverfront or attend a sporting event in the area.
John Blumberg Softball Complex
Catch an event at John Blumberg Softball Complex during your trip to Headingley. Stroll along the riverfront or attend a sporting event in the area.
Explore a world of travel with Expedia
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- Assiniboia Downs
- Assiniboine Park
- Assiniboine Park Zoo
- Beaudry Provincial Park
- Bristol Aerospace Limited
- Brooklands Vacations
- Canadian Forces Base Winnipeg
- Corydon Avenue
- Fortwhyte Alive Center
- Glendale Golf and Country Club
- Grant Park Shopping Centre
- Grant's Old Mill Museum
- John Blumberg Softball Complex
- Kid City
- Leo Mol Sculputure Garden
- Little Mountain Park
- Mcphillips Station Casino
- Polo Park
- Prairie Dog Central Railway
- Red River College
- Red River Exhibition Park
- Saint Francois Xavier Vacations
- Speedworld Indoor Kart Track
- The Players Course
- Thunder Rapids Fun Park
- Tuxedo Vacations
- U-Puttz Thrill Zone
- Unicity Mall
- University of Winnipeg
- Visit Birchwood
- Visit Westdale
- Winnipeg Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
