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 Garden City

Canad Inns Destination Centre Garden City

3 out of 5
Leila-McPhillips Triangle
Price was $870, price is now $757 per person
$757
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) 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.
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $990, price is now $840 per person
$840
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) 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.
Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $888, price is now $763 per person
$763
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) 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.
Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was $950, price is now $817 per person
$817
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) 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.
Country Inn & Suites by Radisson, Winnipeg, MB

Country Inn & Suites by Radisson, Winnipeg, MB

2.5 out of 5
St. James
Price was $967, price is now $846 per person
$846
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Winnipeg (YWG)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

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
$85 nightly
The price is $95 total per night
$95 total
Nov 29 - Nov 30
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
$142 nightly
The price is $159 total per night
$159 total
Nov 29 - Nov 30
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
$100 nightly
The price is $118 total per night
$118 total
Dec 12 - Dec 13
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
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
$102 nightly
The price is $120 total per night
$120 total
Nov 14 - Nov 15
Total with 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
Inn At The Forks

Inn At The Forks

3.5 out of 5
75 Forks Market Rd Winnipeg MB
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $135 total per night
$135 total
Dec 11 - Dec 12
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and wedding services are also provided.
Spa
Pet friendly
Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
1824 Pembina Hwy Winnipeg MB
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $100 total per night
$100 total
Dec 7 - Dec 8
Total with taxes and fees
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.
Pool
Hot Tub
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.

Stay near popular Headingley attractions

John Blumberg Softball Complex

8.0/10 (13 reviews)
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.
See properties

Frequently asked questions

How much are vacation packages to Headingley?
Your vacation dreams can be realized in Headingley from an impressive $757. 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

A rural landscape with a field of tall grass, two grain silos, and a wooden barn under a colorful sky.