Deals on vacations and trips to Headingley

Save when you book Headingley package deals

Choose two or more items and save on your trip:

Headingley flight + hotel 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
per person
Aug 21 - Aug 24
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Winnipeg (YWG)
This eco-certified 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.
Sandman Hotel & Suites Winnipeg Airport

Sandman Hotel & Suites Winnipeg Airport

3 out of 5
St. James
per person
Aug 21 - Aug 24
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
per person
Aug 21 - Aug 24
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Winnipeg (YWG)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, express check-out, and dry cleaning are also offered.
Sandman Signature Winnipeg Airport Hotel & Suites

Sandman Signature Winnipeg Airport Hotel & Suites

3 out of 5
St. James
per person
Aug 21 - Aug 24
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Winnipeg (YWG)
This hotel features 2 restaurants and a bar/lounge. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free airport shuttle. A coffee shop is provided and the front desk is staffed around-the-clock.
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Winnipeg (YWG)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast and free WiFi. Traveling for business? Take advantage of the business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.

Top Headingley hotels deals

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
$116 nightly
The price is $130 total per night
$130 total
Jul 27 - Jul 28
Total includes 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
Motel 6 Headingley, MB - Winnipeg West

Motel 6 Headingley, MB - Winnipeg West

2 out of 5
4400 Portage Avenue, Hwy 101 North, Headingley, MB
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $135 total per night
$135 total
Jul 21 - Jul 22
Total includes 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.
Pool
Pet friendly
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
Get rates
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
Lakeview Signature, Trademark Collection by Wyndham

Lakeview Signature, Trademark Collection by Wyndham

3 out of 5
1999 Wellington Ave, Winnipeg, MB
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $144 total per night
$144 total
Aug 8 - Aug 9
Total includes taxes and fees
This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a 24-hour gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Free airport shuttle
Pet friendly
The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection

The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection

4 out of 5
222 Broadway, Winnipeg, MB
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $155 total per night
$155 total
Jul 20 - Jul 21
Total includes taxes and fees
A full-service spa, 2 restaurants, and a 24-hour gym are all featured at this eco-certified hotel. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. There's a bar/lounge on site, and concierge services and wedding services are also provided.
Spa
Pet friendly
Alt Hotel Winnipeg

Alt Hotel Winnipeg

3 out of 5
310 Donald Street, Winnipeg, MB
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $155 total per night
$155 total
Jul 20 - Jul 21
Total includes 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.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Headingley
View all properties
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

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

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

Frequently asked questions

How much are vacation packages to Headingley?
Your vacation dreams can be realized in Headingley from an impressive $527. 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