Headingley holiday lettings

We found 267 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.

Holiday rentals with weekly discounts - Headingley

Showing deals for:21 Nov - 28 Nov
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Find out more about Headingley

Find out more about Headingley

Why visit Headingley

  • Sports Enthusiasts' Haven: Visit Headingley Stadium for exciting local sporting events and a lively atmosphere.
  • Outdoor Activities: Enjoy scenic golf courses and family-friendly parks, perfect for a day of relaxation and recreation.
  • Charming Accommodation: Choose from private holiday homes, cosy condos, and stylish apartments for a comfortable stay.
  • Cultural Experiences: Explore modern colleges and local attractions that showcase Headingley's rich heritage.
  • Local Hospitality: Experience the warmth of Headingley's community with its welcoming locals and delightful eateries.

Popular types of accommodation in Headingley

If you're looking for the perfect getaway in Headingley, you've come to the right place. Our most popular types of accommodation include houses, cosy condos, and stylish apartments. Whether you're seeking Headingley holiday rentals, holiday lettings, or accommodation near Headingley, we have a range of options to suit your needs. Enjoy transparency, savings, and reassurance as you explore your ideal holiday home in this charming area.

  • Houses: The top choice for visitors to Headingley, these homes offer a comfortable and spacious environment, ideal for families or groups.
  • Condos: A close second, condos provide modern amenities and are perfect for those seeking convenience and a home-away-from-home feel.
  • Apartments: Third in popularity, apartments are an excellent option for couples or solo travellers looking for a cosy stay.
  • Cabins: Fourth on the list, cabins offer a charming escape surrounded by nature, making them a favourite for outdoor enthusiasts.
  • Villas: Rounding out the options, villas deliver a touch of luxury and spacious living for a truly indulgent getaway.**

Top attractions near Headingley

Headingley, Manitoba, offers a delightful mix of attractions for families and business travellers alike. You can explore event venues, modern colleges, and scenic golf courses, catering to those seeking cultural and outdoor experiences. Notable points of interest include Headingley Stadium and various local attractions that enhance your visit. Whether you’re after a leisurely day out or a bustling city experience, Headingley has something for everyone.

  • Red River Exhibition Park: A vibrant event venue hosting a range of exhibitions and conferences, just 1.9km from Headingley. Enjoy a professional atmosphere with diverse activities and entertainment throughout the year.
  • Glendale Golf and Country Club: A welcoming golf course and country club located 1.9km away, perfect for enthusiasts. Engage with friendly locals while enjoying a leisurely round of golf amidst beautiful surroundings.
  • Beaudry Provincial Park: An expansive national park, 2.5km from Headingley, offering thrilling outdoor adventures. Experience stunning scenery and various trails ideal for hiking, biking, and nature exploration.

Things to do recommended for couples

If you're seeking a romantic getaway in Headingley, consider a captivating evening with the Royal Winnipeg Ballet, just 6.8km away, where culture and elegance intertwine. Alternatively, enjoy an exhilarating day at Stony Mountain Ski Area, 11.2km away, perfect for couples who love adventure and the outdoors.

Things to do recommended for families

In Headingley, families can skate at the BellMTS Iceplex, enjoy leisure at John Blumberg Softball Complex, and have a blast at Thunder Rapids Fun Park. These activities offer a perfect blend of adventure, relaxation, and fun for everyone.

Things to do recommended for groups

Explore Polo Park, a vibrant shopping centre 5.6km from Headingley, perfect for group shopping and entertainment. Enjoy a round of golf at John Blumberg Golf Course, located in Headingley, or visit the Forks Market, a bustling public market 7.5km away, ideal for local delicacies and culture.

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

When travelling with a group, family, or pets, or if you're seeking extended stays, it’s important to filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Headingley with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many others on Vrbo.
  • Traveling to Headingley with young kids: Travelling with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with suitable facilities, 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 holiday isn’t truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Headingley: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Headingley

Headingley, Manitoba, offers a delightful blend of family-friendly activities and charming city vibes. Visitors can explore nearby attractions, enjoy cosy cottages, and experience the warmth of local hospitality. Perfect for families and business travellers alike, Headingley serves as an excellent base for exploring the surrounding regions, where romantic getaways and tropical atmospheres await. Whether you seek adventure or relaxation, this lovely destination has something for everyone.

  • Oak Bluff: Oak Bluff is an inviting city located 4.3km from Headingley, offering a delightful blend of outdoor adventure and family-friendly activities. Visitors can immerse themselves in the natural beauty of the nearby national state park, or enjoy the excitement of the local arena entertainment facility. The city also boasts a shopping centre, perfect for those looking to indulge in a bit of retail therapy. Highlights include a historic village that showcases the area’s rich heritage, making Oak Bluff a wonderful destination for families seeking both adventure and education.
  • Tuxedo: Tuxedo, situated 5.0km from Headingley, is a charming neighbourhood that caters to families and business travellers alike. The area features a variety of shopping centres and a shopping mall, offering ample opportunities for a leisurely day out. Golf enthusiasts will appreciate the local golf course, while nature lovers can explore the nearby park, cultural centre, and nature reserve. Tuxedo is perfect for those looking to combine family outings with a touch of business, all within a serene and picturesque setting.
  • Brooklands: Brooklands, a quaint village located 5.6km from Headingley, provides a vibrant community atmosphere ideal for families and business-themed travellers. The village features shopping centres and an arena entertainment facility, ensuring there’s plenty to see and do. Local attractions include a modern college university and a sports facility stadium, making it a great spot for sports enthusiasts and students alike. Brooklands offers a blend of urban convenience with a charming village feel, making it a fantastic destination for a well-rounded vacation experience.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can result in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy area for you to plan new journeys, continue from where you last paused, or view and arrange your travel plans. You’ll discover your saved or booked properties neatly organised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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 (3.3 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 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)
  • 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)

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 rental 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 Vrbo holiday rentals offer amazing value.
How much does it cost to rent a beach house in Headingley?
The average price for a holiday rental 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 Vrbo 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 rental in Headingley?
It's a good idea to check with the Headingley holiday home you're looking at on Vrbo as age restrictions differ. However, typically it's 16, 18 or 21.
How long can I rent a holiday rental 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 Vrbo 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.

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