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Top Holiday Rentals in Headingley

FREE PARKING NY Style Condo in Exchange District
10.0 out of 10, Exceptional, (38)
"The Condo was clean and our host accommodated our needs. I would recommend this property . We were in for a medical appointment, and was relieved when we arrived that the Condo was just as advertised, comfortable and very clean."
The price is £125
per night
14 May - 15 May
FREE PARKING NY Style Condo in Exchange District
Luxurious House in a Desired Location, King Bed
10.0 out of 10, Exceptional, (17)
"The property was clean and spacious! Everything was conveniently located. A perfect place to stay!"
The price is £267
per night
14 May - 15 May
Luxurious House in a Desired Location, King Bed
Bonavista Light House; a 2 bedroom Serene Suite
10.0 out of 10, Exceptional, (19)
"Lewis was an Excellent host - he goes above and beyond to make sure your stay is perfect and ours most definitely was - suite was very clean and super comfortable - we will absolutely be back again - no disappointments here at all."
Bonavista Light House; a 2 bedroom Serene Suite
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NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!
10.0 out of 10, Exceptional, (49)
"Extremely comfortable large condo. Really enjoyed the attention to detail! "
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!
⭐️⭐️ theLOFTonJAMES ⭐️⭐️
10.0 out of 10, Exceptional, (42)
"Nice place for a little getaway. Lots of interesting places in the area."
The price is £293
per night
5 May - 6 May
⭐️⭐️ theLOFTonJAMES ⭐️⭐️
King Bed Astounding Cinematic Sunset in trendy location, South City
10.0 out of 10, Exceptional, (30)
"A great homebase for Winnipeg vacation. Well equipped and well appointed home."
King Bed Astounding Cinematic Sunset in trendy location, South City
Bridgwater Haven. 2 Queen Beds. Private & Clean
10.0 out of 10, Exceptional, (2)
"This is a great location. It’s a walk-in basement just off walking paths in a new sub division. Very clean and has two bedrooms. We would definitely stay again. Thanks for everything."
Bridgwater Haven. 2 Queen Beds. Private & Clean
Modern house in trendy location in South Winnipeg-Bridgwater Area
10.0 out of 10, Exceptional, (13)
"Property centrally located to University, Dining and shopping. Property is fully equipped with everything to ensure a relaxed and enjoyable stay. Very clean and quiet neighbour hood. Would highly recommend this property for short or long term stays!!"
Modern house in trendy location in South Winnipeg-Bridgwater Area
Oasis on the River
10.0 out of 10, Exceptional, (5)
"Very clean and the view of the river was beautiful! Enjoyed going to thermea spa and had a great massage and facial."
Oasis on the River
Afan Home of Joy
9.8 out of 10, Exceptional, (6)
"Clean and comfortable"
The price is £102
per night
5 May - 6 May
Afan Home of Joy
Cozy Skyline Entire Condo in Downtown - Across from Bell MTS Centre
9.8 out of 10, Exceptional, (21)
"Very nice little condo downtown. Perfect for 2 people and very affordable. "
Cozy Skyline Entire Condo in Downtown - Across from Bell MTS Centre
Rare*Full Home in Downtown Winnipeg|Free Parking
9.6 out of 10, Exceptional, (4)
"Beautiful home, great area lots of things close by Safeway right around the corner, safe neighbourhood and awesome property manager"
Rare*Full Home in Downtown Winnipeg|Free Parking
Cozy Wolseley Home!!!
9.6 out of 10, Exceptional, (14)
"Such a cute little place! Clean, well stocked with little extras. Open, easy communication. Hope to book here the next time I am in Winnipeg!"
Cozy Wolseley Home!!!
Le Chalet: Stylish 4bdrm Getaway w/ Hot Tub, Pool
9.6 out of 10, Exceptional, (4)
"The kids loved the hot tub!! It was a great place to be together as a family!!"
Le Chalet: Stylish 4bdrm Getaway w/ Hot Tub, Pool
Cozy Private 1-bedroom Basement Suite with free parking
9.6 out of 10, Exceptional, (18)
"This small basement suite is clean, easy to find in convenient south-west location. Owner is very responsive."
The price is £112
per night
22 May - 23 May
Cozy Private 1-bedroom Basement Suite with free parking
The perfect Retreat
9.6 out of 10, Exceptional, (4)
"Owner was very friendly and house was well maintained "
The price is £148
per night
13 May - 14 May
The perfect Retreat
3 floors character house
9.4 out of 10, Exceptional, (46)
"Very comfortable for us and our dog"
3 floors character house
Restful 4 bedroom TownHome
9.4 out of 10, Exceptional, (3)
"Worked well for a couple hockey families to share during a evaluation camp over the weekend. Was very clean. Basic necessities available in kitchen and bath. Room in the back lane for two SUVs to park side x side. Would stay again. "
Restful 4 bedroom TownHome
Luxurious and Comfortable 3-Bedroom Bungalow Style House
9.2 out of 10, Wonderful, (12)
"Overall our stay was fantastic The house was clean and welcoming home away from home Only issue we had was the dishwasher, so we just washed the dishes"
Luxurious and Comfortable 3-Bedroom Bungalow Style House
Cozy Downtown Loft Rooftop Patio BBQ Gym Coffee
9.2 out of 10, Wonderful, (5)
"Great to be so close to downtown, parked in the parkade across the street and walked everywhere. Would certainly stay again."
Cozy Downtown Loft Rooftop Patio BBQ Gym Coffee
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See all available properties in Headingley
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.

Headingley Holiday Rental Travel Info

Other types of properties in Headingley you may be interested in

Motel 6 Headingley, MB - Winnipeg West
2.0 star property
9.0 out of 10, Wonderful, (1004)
"Nice and comfortable "
The price is £85
per night
13 May - 14 May
Motel 6 Headingley, MB - Winnipeg West
Best Western Plus Winnipeg West
2.5 star property
8.8 out of 10, Excellent, (1002)
"The property is excellent. Staff were great. Only downside was the noise of multiple hockey teams. Staff tried their best to supervise the kids while parents sat in the lobby drinking and socializing. It’s a great hotel just picked a busy weekend "
The price is £105
per night
20 May - 21 May
Best Western Plus Winnipeg West
Lakeview Signature, Trademark Collection by Wyndham
3.0 star property
8.8 out of 10, Excellent, (1316)
"So good to be able to walk to this hotel, when coming in late from a flight at Winnipeg Airport. Its always clean, quiet and comfortable. The staff is always pleasant and willing to help with anything we need. The waitress in the restaurant at breakfast is always so pleasant and efficient. It feels like staying with family. "
The price is £115
per night
17 May - 18 May
Lakeview Signature, Trademark Collection by Wyndham
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.

Everything you need to know about Headingley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Headingley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Headingley holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Headingley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Headingley holiday rentals we have selected for you start as low as £102 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Headingley rentals

At Expedia, we put the best Headingley holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Headingley?

Yes, there are holiday rentals in Headingley close to BellMTS Iceplex, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Headingley has a good selection of coffee shops. Make sure you have time to check out the hockey games and riverfront during your trip.

What are some of the best holiday rentals that Headingley has to offer?

Luxurious and Comfortable 3-Bedroom Bungalow Style House: This holiday home rental outside of Headingley is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Headingley?

Family-friendly attractions include BellMTS Iceplex and Thunder Rapids Fun Park, whereas Beaudry Provincial Park is a spot to enjoy the outdoors. While here, Red River Exhibition Park and John Blumberg Golf Course are other places worth a visit.

What are holiday rentals like in Headingley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Headingley. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for families.

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