Headingley vacation rentals

We found 270 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Headingley that are perfect for your trip. Vacation homes offer the amenities you expect for your stay with friends, family, or just your pet, such as parking and a fireplace. At the end of the day, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.
  • 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, yards and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about Headingley

Find out more about Headingley

Why visit Headingley

  1. Family-friendly attractions: Headingley offers a variety of activities suitable for all ages, making it perfect for family vacations.
  2. Cultural experiences: Explore local cultural venues and events that showcase the community's rich heritage.
  3. Natural beauty: Enjoy the serene landscapes and outdoor activities that blend city life with nature.
  4. Friendly community: Experience the welcoming atmosphere of Headingley and engage with local residents.
  5. Flexible accommodations: Choose from a range of vacation rentals, including cozy homes and modern condos.

Popular types of accommodation in Headingley

Discover the charm of Headingley with our selection of vacation rentals. Whether you’re looking for a cozy private vacation home, a modern condo, or a spacious apartment, we have the perfect accommodation for your stay. Our offerings include new apartments and bed townhouses, ensuring you find the ideal rental for your needs. Enjoy transparency, savings, and reassurance as you explore Headingley!

  • Houses: The top choice among visitors to Headingley, these homes offer spacious and comfortable accommodations for families and friends.
  • Condos: A popular option for those seeking modern amenities and a convenient location, condos provide a stylish stay in Headingley.
  • Apartments: Ideal for solo travellers or couples, apartments offer a cozy and private atmosphere for your getaway.
  • Cabins: Perfect for nature enthusiasts, cabins provide a rustic and tranquil retreat amidst the beautiful landscape.
  • Villas: For a touch of luxury, villas offer expansive spaces and upscale features for a memorable vacation experience.**

Top attractions in Headingley

Headingley, Manitoba, offers a delightful mix of family-friendly, city-themed, and business-oriented activities. Visitors can explore popular attractions such as event and conference venues, modern colleges and universities, and environmental centres. Whether you're seeking cultural experiences, outdoor adventures, or a vibrant city atmosphere, Headingley has something for everyone to enjoy during their stay.

  1. Red River Exhibition Park: This vibrant event venue, located 4.8km from Headingley, is perfect for those who enjoy business and networking events. It features a variety of exhibitions and entertainment, making it a lively spot to experience local culture.
  2. Glendale Golf and Country Club: Situated 4.8km from Headingley, this welcoming golf club offers a friendly atmosphere, perfect for both seasoned golfers and beginners. Enjoy a round of golf surrounded by beautiful landscapes.
  3. Historical Museum of St. James - Assiniboia: Located 8.0km away, this museum immerses visitors in local history and culture, showcasing fascinating exhibits that highlight the region’s rich heritage.

Things to do recommended for couples

Headingley offers delightful couple experiences! Enjoy a captivating performance at the Royal Winnipeg Ballet, only 17.7km away, for a blend of romance and culture. For adventure, head to Stony Mountain Ski Area, 29.0km away, where you can embrace the thrill of skiing together.

Things to do recommended for families

Your family will have a blast at the BellMTS Iceplex for ice skating, the John Blumberg Softball Complex for relaxation, and Academy Lanes West for arcade adventures, all within a short drive from Headingley. Enjoy a mix of sports, wellness, and family fun!

Things to do recommended for groups

Explore Polo Park for shopping and entertainment, enjoy a day at the John Blumberg Golf Course for some outdoor fun, and visit Forks Market for a taste of local culture and cuisine, all while soaking in the vibrant atmosphere of Headingley.

What do I need to keep in mind when booking a vacation in Headingley

If you're travelling with a group, family, pets, or planning an extended stay, it's important to filter your options according to your specific needs. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Headingley with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group activities. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Headingley with young kids: Travelling with young children can present its challenges. It’s important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Headingley: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many pet-friendly accommodations offer feeding bowls and beds, ensuring that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Headingley: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search as well.

Where to stay in Headingley

Headingley, Manitoba, is a charming destination perfect for family vacations and business trips alike. Explore the friendly community and experience the beautiful central area, where you’ll find a delightful mix of city life and nature. Venture into the heart of Headingley, where you can enjoy a welcoming atmosphere and engage with local attractions. Nearby, the essence of West Yorkshire adds to the allure, making your stay truly memorable.

  • Oak Bluff: Located 11.3km from Headingley, Oak Bluff is a vibrant community that appeals to outdoor enthusiasts and families alike. This charming city offers a variety of recreational activities, including access to national parks and a local stadium for sports events. Visitors can enjoy the education and entertainment facilities at the arena, as well as shopping at the local centre. The blend of adventure and family-oriented experiences makes Oak Bluff a delightful stop on your journey.
  • Tuxedo: Situated 12.9km from Headingley, Tuxedo is a picturesque neighbourhood known for its family-friendly atmosphere and outdoor adventures. The area features a shopping mall and a variety of shopping centres, making it a great destination for those looking to indulge in retail therapy. Nature lovers will appreciate the nearby parks and nature reserves, while culture enthusiasts can explore the local cultural centre. Tuxedo strikes a perfect balance between leisure and business, creating a well-rounded travel experience.
  • Brooklands: Just 14.5km from Headingley, Brooklands is a quaint village that offers a mix of family and business experiences. Visitors can explore the local shopping centres and malls, as well as enjoy the entertainment options at the arena. The village is home to modern educational institutions, such as a college university, and boasts a vibrant sports culture with its stadium and sports facilities. Brooklands provides a welcoming environment for families and professionals searching for a city-like experience while maintaining a small-town charm.

Best time to go to Headingley

If you're planning a trip to Headingley, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and July, while off-peak times, like February and October to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January5.2°F (-14.9°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
February5.2°F (-14.9°C)No Rain (Dry)Mostly CloudySlightly LowSlightly Low
March22.5°F (-5.3°C)No Rain (Dry)Mostly CloudySlightly HighSlightly Low
April37.4°F (3.0°C)No Rain (Dry)Mostly CloudySlightly HighAverage
May53.6°F (12.0°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
July68.7°F (20.4°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
September59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
October43.7°F (6.5°C)Light RainMostly SunnySlightly LowAverage
November26.8°F (-2.9°C)No Rain (Dry)Mostly CloudySlightly LowAverage
December11.1°F (-11.6°C)No Rain (Dry)Mostly CloudyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking an extended stay for even greater savings. To discover a Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo's innovative Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and organize your travel arrangements. You can now access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Travel to friendly Headingley

The area's festivals and museums are just a few of the reasons to vacation in Headingley. Travelers to this welcoming city praise the hockey games, riverfront and coffeehouses. 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 searching for attractions to see in the area? Venture out of your vacation home and experience everything that makes Headingley a fun spot to vacation. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Assiniboia Downs (3.3 mi / 5.3 km)
  • Assiniboine Park Zoo (6.7 mi / 10.8 km)
  • Thermëa - Winnipeg (11.4 mi / 18.4 km)
  • Buhler Recreation Park (18.3 mi / 29.4 km)
  • Tinkertown (18.4 mi / 29.6 km)
  • BellMTS Iceplex (3 mi / 4.8 km)

Exploring the natural features in Headingley

Whether you're an active traveler or just want to take in the scenery, Headingley is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Assiniboine Park (6.9 mi / 11.1 km)
  • Plaza at the Forks (11.7 mi / 18.8 km)
  • Saint Norbert Provincial Heritage Park (13.5 mi / 21.8 km)
  • Leo Mol Sculputure Garden (6.9 mi / 11.1 km)
  • FortWhyte Alive Center (8.1 mi / 13 km)
  • Little Mountain Park (8.9 mi / 14.3 km)

Transportation to and around Headingley

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

Frequently asked questions

What is the best area to stay in Headingley when booking a vacation rental?
When considering a vacation rental in Headingley, Manitoba, one of the most appealing areas to stay is around the Headingley Riverfront. This lovely neighbourhood offers a serene atmosphere with scenic views of the Assiniboine River, making it superb for those who appreciate nature and outdoor activities. The riverfront area is not only picturesque but also provides access to walking trails and parks, ideal for leisurely strolls or picnics.

Another excellent option is the Headingley Business Park area, which is conveniently located near local amenities and services. This neighbourhood is close to popular attractions such as the Assiniboine Park Zoo, where visitors can enjoy a day of exploring wildlife, and the nearby Assiniboine Park itself, which features beautiful gardens and recreational facilities.
How much does it cost to rent a vacation home in Headingley?
Prices for vacation rentals in Headingley vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Headingley to more spacious homes.
Are there any discounts for Headingley vacation house rentals?
You can find great discounts on house rentals in Headingley on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Headingley?
A long-stay vacation rental in Headingley is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Headingley vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Headingley with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Headingley for a vacation rental?
March marks the beginning of the peak season in Headingley, Manitoba, making it a popular choice for those looking to enjoy springtime adventures. This month typically ushers in milder temperatures, averaging around 5°C, which provides a comfortable climate for outdoor activities like hiking and cycling. As the snow melts away, the vibrant natural scenery reawakens, inviting visitors to explore the beautiful trails and parks nearby.

The peak season extends from March through May, attracting nature enthusiasts and families eager to experience the blossoming landscapes. During this time, Headingley hosts various community events and outdoor festivals, creating a lively atmosphere that complements the stunning surroundings.

For those seeking a more budget-friendly option, consider visiting in October. This month presents a unique opportunity to witness the beautiful autumn foliage and enjoy the tranquil ambiance of Headingley. The crisp air and the stunning fall colours make for great walking conditions, allowing for peaceful exploration of the area.
How early should I book a Headingley vacation rental?
Book your Headingley vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Headingley?
In Headingley, visitors can discover several attractions that showcase the region's charm. The Assiniboine River offers picturesque views and opportunities for outdoor activities, such as kayaking and fishing. Vacation rentals in this area often feature spacious designs with scenic vistas, making them ideal for families or groups looking to enjoy the natural surroundings.
Can I change or cancel my Headingley home rental booking on Vrbo?
To find Headingley vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Headingley vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Vacation Rentals ideas

People also search for