Deals on vacations and trips to Headingley

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Headingley flight + hotel vacation packages

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 $920, price is now $825 per person
$825
per person
May 10 - May 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
This smoke-free hotel features free water park access, a nightclub, and a restaurant. Bring the family and enjoy the children's pool, waterslide, and kid-friendly dining. Enjoy the indoor pool and perks like free self parking and free WiFi.
Sandman Hotel & Suites Winnipeg Airport

Sandman Hotel & Suites Winnipeg Airport

3 out of 5
St. James
Price was $1,206, price is now $989 per person
$989
per person
May 10 - May 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like free self parking.
Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $1,092, price is now $930 per person
$930
per person
May 10 - May 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Bring the family and enjoy the children's pool, waterslide, and kid-friendly dining. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $1,059, price is now $909 per person
$909
per person
May 10 - May 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Bring the family and enjoy the free kid's club, children's pool, and kid-friendly dining. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Days Inn & Suites by Wyndham Winnipeg Airport Manitoba

Days Inn & Suites by Wyndham Winnipeg Airport Manitoba

2.5 out of 5
St. James
Price was $1,195, price is now $1,096 per person
$1,096
per person
May 10 - May 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Top Headingley hotels deals

Motel 6 Headingley, MB - Winnipeg West

Motel 6 Headingley, MB - Winnipeg West

2 out of 5
4400 Portage Avenue Headingley MB
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $106 total per night
$106 total
Mar 22 - Mar 23
Total with taxes and fees
An indoor pool, free self parking, and laundry facilities are featured at this motel. WiFi in public areas is free. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.
Best Western Plus Winnipeg West

Best Western Plus Winnipeg West

2.5 out of 5
4140 Portage Avenue Headingley MB
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $150 total per night
$150 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
1808 Wellington Ave Winnipeg MB
Free Cancellation
Reserve now, pay when you stay
$117 nightly
The price is $139 total per night
$139 total
Mar 17 - Mar 18
Total with taxes and fees
Free water park access, a gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the indoor pool and perks like free WiFi and a free airport shuttle.
Pool
Hot Tub
The Grand Winnipeg Airport Hotel by Lakeview

The Grand Winnipeg Airport Hotel by Lakeview

4 out of 5
1979 Wellington Ave. Winnipeg MB
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $134 total per night
$134 total
Apr 3 - Apr 4
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, express check-out, and a computer station are also offered.
Free WiFi
Restaurant
Alt Hotel Winnipeg

Alt Hotel Winnipeg

3 out of 5
310 Donald Street Winnipeg MB
$111 nightly
The price is $131 total per night
$131 total
Mar 31 - Apr 1
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.
Birchwood Inn, BW Premier Collection

Birchwood Inn, BW Premier Collection

3 out of 5
2520 Portage Ave Winnipeg MB
Free Cancellation
Reserve now, pay when you stay
$117 nightly
The price is $138 total per night
$138 total
Mar 17 - Mar 18
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
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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.

Popular places to visit

John Blumberg Golf Course

Enjoy a round of golf in Headingley at John Blumberg Golf Course. Experience the area's fascinating museums or attend a sporting event.

John Blumberg Golf Course

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.

Thunder Rapids Fun Park

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.

John Blumberg Softball Complex

Frequently asked questions

How much are vacation packages to Headingley?
Your vacation dreams can be realized in Headingley from an impressive $825. Vacation packages include flights and hotels, and they'll make your booking nice and easy. The only thing you'll have to focus on is what amazing attraction you'll head to first.
How long should my Headingley vacation be?
About 2 nights is what most tourists book for their Headingley trip. That's a good guide, but there's loads more to uncover if you allow yourself a couple of extra days.
Where can I get the best vacation package deals for Headingley?
Travelocity is the only place you need to go to score a fantastic Headingley package deal. Select from as many as 400 air carriers and 1,000,000 properties across the globe and craft a vacation package that fits your style. With so many options at hand, you'll have plenty of inspiration for your next big adventure.
Why should I book my Headingley vacation bundle via Travelocity?
We offer 24/7 support, high-quality service and a Price Match Guarantee. Life is one big journey — and we have incredible destinations for you to journey to all across the world. Roam with us and your wallet will thank you for it.
Can I save money on my Headingley car rental if I combine it with a hotel or flight?
Combining your bookings into a Headingley vacation package will save you a handsome sum. Choose a car and flight; a flight, car and hotel; or a hotel and car. There's no better way to discover the greater Headingley area than with your own ride. You can also add experiences and tours to your Travelocity package.
What is there to do in Headingley?
Take advantage of the great photo-ops at BellMTS Iceplex, one of the most famous attractions in Headingley. There's a lot more to discover around this exciting city, so make sure you have enough time to explore some off-the-beaten-path gems.
Where should I stay when visiting Headingley?
Many people stay at the Best Western Plus Winnipeg West. It's sure to be a great base for your Headingley getaway.

Photos of local treasures

Browse Headingley vacation photos for more inspiration