Headingley Holiday Rentals

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Holiday Rentals in Headingley

Interior
FREE PARKING NY Style Condo in Exchange District
10.0 out of 10, Exceptional, (39)
"A great place to stay for downtown business. Was able to walk to the Jets playoff game!!"
The price is NZ$255
per night
28 May - 29 May
FREE PARKING NY Style Condo in Exchange District
TV
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!
10.0 out of 10, Exceptional, (50)
"Extremely comfortable large condo. Really enjoyed the attention to detail! "
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!
Interior
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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Exterior
⭐️⭐️ theLOFTonJAMES ⭐️⭐️
10.0 out of 10, Exceptional, (43)
"This place was amazing—beyond our expectations! Though there are plenty of places to go within walking distance, you will most likely just want to stay in and admire the art gallery/museum-like charm of this place. There’s so much to look at, yet it’s still cozy and welcoming! Our host greeted us with wine and desserts, told us about the local hotspots, and checked in with us regularly to see if we needed anything. We can’t wait to come back and stay here!!"
The price is NZ$573
per night
15 May - 16 May
⭐️⭐️ theLOFTonJAMES ⭐️⭐️
Pool
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
Pool
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 NZ$518
per night
15 May - 16 May
Luxurious House in a Desired Location, King Bed
2 bedrooms, iron/ironing board, WiFi, bed sheets
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
Fridge, microwave, oven, stovetop
Oasis on the River
10.0 out of 10, Exceptional, (5)
"It was amazing to stay here. Gonna try to rent this house again. Told friends about it. The deer,geese,squirrels they were amazing to see in the backyard. Very nice. The floor is kinda wonky but other than that nicest place I stayed in on vrbo. Pricey but worth it. Too bad it wasn’t pet friendly so I could bring my dog next time. Enjoyed the stay."
Oasis on the River
Living area
Downtown luxury 1 bedroom sleeps 4 wifi and laundry across arena
10.0 out of 10, Exceptional, (2)
"Overall it was good."
The price is NZ$312
per night
19 May - 20 May
Downtown luxury 1 bedroom sleeps 4 wifi and laundry across arena
Fridge, microwave, oven, stovetop
Recently renovated home just a 7 minute walk from the St Boniface Hospital.
10.0 out of 10, Exceptional, (2)
"It was a great property, so authentic, kudos to Anna for keeping it historical with all the old stuff. The house was so charming with easy access to many places."
Recently renovated home just a 7 minute walk from the St Boniface Hospital.
Property grounds
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
Property grounds
Afan Home of Joy
9.8 out of 10, Exceptional, (6)
"Clean and comfortable"
The price is NZ$207
per night
21 May - 22 May
Afan Home of Joy
Fridge, microwave, oven, stovetop
Rare*Full Home in Downtown Winnipeg|Free Parking
9.6 out of 10, Exceptional, (5)
"Great location, clean, lots of room as advertised"
Rare*Full Home in Downtown Winnipeg|Free Parking
Property grounds
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
Interior
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 NZ$227
per night
28 May - 29 May
Cozy Private 1-bedroom Basement Suite with free parking
Living area
Luxurious 2 bedroom basement suit.
9.6 out of 10, Exceptional, (11)
"Very nice neighborhood,suite was beautiful "
Luxurious 2 bedroom basement suit.
Outdoor dining
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!!!
Fridge, microwave, oven, stovetop
3 floors character house
9.4 out of 10, Exceptional, (46)
"Very comfortable for us and our dog"
3 floors character house
Fridge, microwave, stovetop, coffee/tea maker
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
Exterior
Luxurious Downtown Loft Heated Parking Rooftop Patio BBQ Gym Coffee
9.4 out of 10, Exceptional, (9)
"Would love to stay here again. Great location"
Luxurious Downtown Loft Heated Parking 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.

Other types of properties in Headingley you may be interested in

Lobby
Motel 6 Headingley, MB - Winnipeg West
2.0 star property
9.0 out of 10, Wonderful, (1006)
"Very clean."
The price is NZ$177
per night
20 May - 21 May
Motel 6 Headingley, MB - Winnipeg West
Exterior
Best Western Plus Winnipeg West
2.5 star property
8.8 out of 10, Excellent, (1005)
"We keep on coming back here everytime we feel like away from home.I always keep in mind the deals here before booking.My kids love the pool and the breakfast is really awesome.We love this place.."
The price is NZ$219
per night
26 May - 27 May
Best Western Plus Winnipeg West
Water park
Victoria Inn Hotel and Convention Centre Winnipeg
3.0 star property
8.4 out of 10, Very good, (1351)
"The request you have to get room service"
The price is NZ$233
per night
27 May - 28 May
Victoria Inn Hotel and Convention Centre Winnipeg
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Headingley holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Headingley. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Headingley. Seeing all the best attractions is bound to make you fall in love with Headingley. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Headingley short-term rentals, that won’t be hard to do.

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.

Recent reviews of Headingley properties
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