Deals on vacations and trips to Headingley

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

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
Price was $780, price is now $726 per person
$726
per person
Feb 11 - Feb 13
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
This smoke-free hotel features free water park access, a nightclub, and 2 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Enjoy the indoor pool and perks like free self parking.
Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was $866, price is now $792 per person
$792
per person
Feb 11 - Feb 13
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
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.
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $808, price is now $742 per person
$742
per person
Feb 11 - Feb 13
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

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

4 out of 5
Downtown Winnipeg
Price was $831, price is now $778 per person
$778
per person
Feb 11 - Feb 13
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
A full-service spa, 2 restaurants, and a 24-hour gym are all featured at this Victorian 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.
Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $772, price is now $727 per person
$727
per person
Feb 11 - Feb 13
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

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
$74 nightly
The price is $82 total per night
$82 total
Dec 22 - Dec 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.
Pool
Pet friendly
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
$124 nightly
The price is $139 total per night
$139 total
Dec 31 - Jan 1, 2026
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
$96 nightly
The price is $114 total per night
$114 total
Dec 23 - Dec 24
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
Sandman Hotel & Suites Winnipeg Airport

Sandman Hotel & Suites Winnipeg Airport

3 out of 5
1750 Sargent Ave Winnipeg MB
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $140 total per night
$140 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
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.
Pool
Hot Tub
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

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

4 out of 5
222 Broadway Winnipeg MB
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $137 total per night
$137 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
A full-service spa, 2 restaurants, and a 24-hour gym are all featured at this Victorian 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
Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
1415 Regent Ave W Winnipeg MB
Free Cancellation
Reserve now, pay when you stay
$74 nightly
The price is $87 total per night
$87 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
Parking included
Free WiFi
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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

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 $726. 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