Headingley Holiday Rentals

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Holiday Rentals in Headingley

Luxury 2 bed 2 Bath Across Jets Arena 16th Floor With Amazing View
8.8 out of 10, Excellent, (14)
"Rental is as advertised. If you want to be close to the action for jets games or concerts, this is the one. Great for 2 couples staying, as there are 2 bathrooms to offer some extra privacy. Some general aaesthetic maintenance needed in the space but nothing affecting our stay."
Luxury 2 bed 2 Bath Across Jets Arena 16th Floor With Amazing View
Basement guest suite with separate entrance
8.8 out of 10, Excellent, (23)
"Was an awesome place just what we needed ."
The price is AU$129
includes taxes & fees
8 June - 9 June
Basement guest suite with separate entrance
Luxurious and Comfortable 3-Bedroom Bungalow Style House
8.8 out of 10, Excellent, (13)
"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
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2 bed downtown sleeps 6 across jets arena
8.6 out of 10, Excellent, (17)
"Property was nice and close to the arena"
2 bed downtown sleeps 6 across jets arena
Cozy 3BR near Airport/DTown/Mall
9.0 out of 10, Wonderful, (2)
"Good communication: supplied everything we needed for a quick weekend in and out of Winnipeg and close to the airport."
The price is AU$357
includes taxes & fees
4 June - 5 June
Cozy 3BR near Airport/DTown/Mall
Executive Luxury 2 bed Spacious Downtown WIFI laundry across sleeps 6
7.4 out of 10, Good, (6)
" Great communication. Received the information needed to access the unit and had no issues to mention. Once in the unit, there was a binder with all the other tidbits of info needed. My son and I had a great time there and at the Jets game."
Executive Luxury 2 bed Spacious Downtown WIFI laundry across sleeps 6
3 floors character house
9.4 out of 10, Exceptional, (46)
"Very comfortable for us and our dog"
3 floors character house
FREE PARKING NY Style Condo in Exchange District
10.0 out of 10, Exceptional, (40)
"Excellent location, parking was a breeze. Definitely will book again."
The price is AU$234
includes taxes & fees
11 June - 12 June
FREE PARKING NY Style Condo in Exchange District
Gorgeous 2 bed Sleeps 6 w/ Surreal View Downtown Laundry Wifi
8.0 out of 10, Very good, (9)
"Was A good spot for our parents to stay back with our toddler while we went to a concert downtown. Very good location, check ahead of time to see if you can get parking. Hosts were helpful and quick to respond. The place was clean where it counted. Fresh sheets and towels etc. It could have used some dusting etc. It was early spring so the balcony and windows weren’t very clean which is understandable. Would definitely stay again."
Gorgeous 2 bed Sleeps 6 w/ Surreal View Downtown Laundry Wifi
Afan Home of Joy
9.8 out of 10, Exceptional, (7)
"Wonderful property, will definitely recommend"
The price is AU$191
includes taxes & fees
9 June - 10 June
Afan Home of Joy
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
Cozy Wolseley Home!!!
9.4 out of 10, Exceptional, (16)
"Excellent stay for small family. "
Cozy Wolseley Home!!!
Oasis on the River
9.8 out of 10, Exceptional, (6)
"Enjoyed the lovely river view especially early morning when environment is quite. The moon reflection in the river at 4am looks amazing."
Oasis on the River
Home away from home!
8.8 out of 10, Excellent, (8)
"It was a great stay with great amenities. Highly recommended for a comfortable stay."
The price is AU$208
includes taxes & fees
7 June - 8 June
Home away from home!
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!
10.0 out of 10, Exceptional, (52)
"This spot has a funky feel with lots of open space. Close to downtown without the busy streets."
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!
Oceanfront 4th Floor, 2 Bedroom Condo on the Boardwalk!
9.2 out of 10, Wonderful, (44)
"This condo hes a beautiful view of the ocean.Condo is equipped with everything you ever need.Steps away from boardwalk and the beach.The place was very clean ,comfy and cozy.Easy check-in, check-out.The menager was very helpful.We highly recommended this place."
Oceanfront 4th Floor, 2 Bedroom Condo on the Boardwalk!
Executive 2 bed Condo King bed great LOCATION
9.0 out of 10, Wonderful, (16)
"Overall this beats a hotel and I will stay here again but there were small issues as to be expected. 1. No sheets on either bed, just a comforter, this was very strange. 2. Could not get TV volume to work. 3. I dropped something in the bedroom and when I bent to pick it up there was stuff under the bed and nightstand. Hadn't been cleaned in a long time. View was great, location even better especially for anything going on at the arena. Parking was handy right next door. Price was decent and...
Executive 2 bed Condo King bed great LOCATION
⭐️⭐️ theLOFTonJAMES ⭐️⭐️
10.0 out of 10, Exceptional, (44)
"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 AU$526
includes taxes & fees
4 June - 5 June
⭐️⭐️ theLOFTonJAMES ⭐️⭐️
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
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."
The price is AU$496
includes taxes & fees
18 June - 19 June
King Bed Astounding Cinematic Sunset in trendy location, South City
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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 Home Travel Info

Other types of properties in Headingley you may be interested in

Best Western Plus Winnipeg West
2.5 star property
8.8 out of 10, Excellent, (1003)
"Enjoyed our stay was clean and breakfast options were good"
The price is AU$202
includes taxes & fees
17 June - 18 June
Best Western Plus Winnipeg West
Motel 6 Headingley, MB - Winnipeg West
2.0 star property
9.0 out of 10, Wonderful, (1005)
"Property was very quiet. Rooms were clean, and the staff were friendly. "
The price is AU$173
includes taxes & fees
25 June - 26 June
Motel 6 Headingley, MB - Winnipeg West
Victoria Inn Hotel and Convention Centre Winnipeg
3.0 star property
8.4 out of 10, Very good, (1390)
"I had a great stay at this hotel. I was very impressed with the way your staff was so welcoming to Indigenous people staying at the hotel. This means a lot to me as the parent of an indigenous child. "
The price is AU$219
includes taxes & fees
14 June - 15 June
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.

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, 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 favourite 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 depend 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 AU$129 per night. Entering your travel dates in the search wizard might find you 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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