Headingley Vacation Rentals from $103: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Headingley?

3000 sq.ft 5 Beds , 4 bedrooms 3 Full Bath : This vacation home rental outside of Headingley offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Headingley vacation rentals

Cheerful Tuxedo House with Hot Tub

Tuxedo

peter S.

$583 nightly

Mar 2 - Mar 3

Total with taxes and fees

Separate Entrance Basement Suite

Fort Garry

Alabi A.

$91 nightly

Mar 1 - Mar 2

Total with taxes and fees

Prairie Luxury 2 Bedrooms Home

Fort Garry

Bels45

$169 nightly

Mar 2 - Mar 3

Total with taxes and fees

Welcoming Private 2 Bedroom Suite

Fort Garry

Mila D.

$111 nightly

Mar 4 - Mar 5

Total with taxes and fees

2 bedrooms, iron/ironing board, WiFi, bed sheets

Mary's Luxury Suite

Fort Garry

Patricia S.

$115 nightly

Mar 3 - Mar 4

Total with taxes and fees

3000 sq.ft 5 Beds , 4 bedrooms 3 Full Bath

Fort Garry

Val D.

$241 nightly

Mar 1 - Mar 2

Total with taxes and fees

Golden Eagle, Basement Suite

Winnipeg

Lesly

$94 nightly

Mar 1 - Mar 2

Total with taxes and fees

Magnificent Stylish Escape

Fort Garry

$1,027 nightly

Feb 28 - Mar 1

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Private vacation homes

Condos

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Headingley Hotel Reviews

Super 8 by Wyndham Winnipeg East MB

10/10 Excellent

"Room was clean, front desk staff was so helpful and nice."

Find out more about Headingley

Everything you need to know about Headingley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Headingley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Headingley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Headingley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Headingley. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Headingley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $103 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Headingley rentals

At Expedia, we put the best Headingley vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Headingley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Headingley vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Headingley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Headingley?

Yes, you can find vacation rentals in Headingley close to Thunder Rapids Fun Park, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Headingley has a good selection of coffeehouses. Make sure you have time to check out the hockey games and riverfront during your trip.

What are some of the best vacation rentals in Headingley?

3000 sq.ft 5 Beds , 4 bedrooms 3 Full Bath: This vacation home rental outside of Headingley offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

What can I see and do in Headingley?

While exploring the area, visit family-friendly sights like Thunder Rapids Fun Park, or get outside and enjoy nature at Assiniboine Park. While here, John Blumberg Golf Course and John Blumberg Softball Complex are other places worth a visit.

What are vacation rentals like in Headingley?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Headingley. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.

Room 1

Check prices for these dates