Headingley holiday rentals

We found 310 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Headingley that are perfect for your trip. Holiday homes provide the best amenities for you and your friends, family or even pets, such as a pool and a washer and dryer. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Travel to friendly Headingley

The area's festivals and museums are just some of the reasons to come on holiday to Headingley. Travellers to this welcoming city praise the hockey games, riverfront and coffee shops. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Headingley

Are you looking for attractions to see while you're in town? Venture out of your cosy holiday rental and experience everything that makes Headingley a fun place to get away to. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Assiniboia Downs (3.6 mi / 5.7 km)
  • Assiniboine Park Zoo (6.7 mi / 10.8 km)
  • Thermëa - Winnipeg (11.4 mi / 18.4 km)
  • The Meadows at East St. Paul Golf Course (17.5 mi / 28.1 km)
  • Buhler Recreation Park (18.3 mi / 29.4 km)
  • BellMTS Iceplex (3 mi / 4.8 km)

Exploring the natural features in Headingley

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Headingley is a great spot to appreciate mother nature. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Assiniboine Park (6.9 mi / 11.1 km)
  • Plaza at the Forks (11.7 mi / 18.8 km)
  • Leo Mol Sculputure Garden (6.9 mi / 11.1 km)
  • FortWhyte Alive Center (8.1 mi / 13 km)
  • Old Market Square (11.3 mi / 18.3 km)
  • St. Vital Park (11.4 mi / 18.3 km)

Transport to and around Headingley

The nearest airport is in Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.), located 7.9 mi (12.7 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Headingley?
Property type, length of stay and season are some things that can influence the price of a holiday home. Simply click on your dates of travel to find your perfect match. From cosy cabins to sprawling luxury villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Headingley?
The average price for a holiday home close to the beach in Headingley depends on when you’re going and the style and size of property you’re searching for. You can quickly and easily find prices on Stayz by entering your preferred travel dates and destination. Then use our filter tool to pick the number of bedrooms and amenities that you require, like air conditioning, WiFi and a hot tub.
What are the top attractions for families in Headingley?
Keeping the kids happy during your holiday in Headingley is a breeze with these leading family-friendly attractions:

  • Assiniboine Park Zoo
  • Assiniboine Park
  • Western Canada Aviation Museum

How old do you have to be to rent a holiday home in Headingley?
It’s a good idea to check with the Headingley holiday home you’re looking at on Stayz as age restrictions differ. However, typically it’s 16, 18 or 21.
How long can I rent a holiday home in Headingley for?
It all depends on the Headingley property. To see all available options offering extended stays, just enter your travel dates and number of people into the Stayz search page. You can enjoy having the whole place to yourself, along with comforts such as air conditioning, a kitchen and a yard where the kids can burn off energy. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

More Holiday Rentals ideas

People also search for