Headingley Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Headingley

Luxury 2 bed 2 Bath Across Jets Arena 16th Floor With Amazing View
8.6 out of 10, Excellent, 15 reviews
"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
3 floors character house
9.4 out of 10, Exceptional, 46 reviews
"Very comfortable for us and our dog"
3 floors character house
Cozy Wolseley Home!!!
9.4 out of 10, Exceptional, 16 reviews
"Excellent stay for small family. "
Cozy Wolseley Home!!!
Save an average of 15% on thousands of hotels when you're signed in
Basement guest suite with separate entrance
8.8 out of 10, Excellent, 23 reviews
"Was an awesome place just what we needed ."
The price is CA $60
CA $114 total
includes taxes & fees
Jun 9 - Jun 10
Basement guest suite with separate entrance
Cozy 3BR near Airport/DTown/Mall
9.0 out of 10, Wonderful, 2 reviews
"Good communication: supplied everything we needed for a quick weekend in and out of Winnipeg and close to the airport."
The price is CA $170
CA $319 total
includes taxes & fees
Jun 9 - Jun 10
Cozy 3BR near Airport/DTown/Mall
Luxurious and Comfortable 3-Bedroom Bungalow Style House
8.8 out of 10, Excellent, 13 reviews
"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
2 bed downtown sleeps 6 across jets arena
8.6 out of 10, Excellent, 17 reviews
"Property was nice and close to the arena"
2 bed downtown sleeps 6 across jets arena
Executive Luxury 2 bed Spacious Downtown WIFI laundry across sleeps 6
7.4 out of 10, Good, 6 reviews
" 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
Gorgeous 2 bed Sleeps 6 w/ Surreal View Downtown Laundry Wifi
8.0 out of 10, Very good, 9 reviews
"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
FREE PARKING NY Style Condo in Exchange District
10.0 out of 10, Exceptional, 40 reviews
"Excellent location, parking was a breeze. Definitely will book again."
The price is CA $104
CA $210 total
includes taxes & fees
Jun 11 - Jun 12
FREE PARKING NY Style Condo in Exchange District
Oasis on the River
9.8 out of 10, Exceptional, 6 reviews
"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
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!
10.0 out of 10, Exceptional, 52 reviews
"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 !!
Rare*Full Home in Downtown Winnipeg|Free Parking
9.6 out of 10, Exceptional, 5 reviews
"Great location, clean, lots of room as advertised"
Rare*Full Home in Downtown Winnipeg|Free Parking
Restful 4 bedroom TownHome
9.4 out of 10, Exceptional, 3 reviews
"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
Home away from home!
8.8 out of 10, Excellent, 8 reviews
"It was a great stay with great amenities. Highly recommended for a comfortable stay."
The price is CA $99
CA $186 total
includes taxes & fees
Jun 11 - Jun 12
Home away from home!
⭐️⭐️ theLOFTonJAMES ⭐️⭐️
10.0 out of 10, Exceptional, 44 reviews
"Let’s start with the basics - very clean, spacious, comfortable, very well stocked, excellent host. All five stars. But the truly amazing aspect of this unit was the absolutely incredible work they did on the interior design. Basically, they gutted an old warehouse and created an amazing living space. Warm and inviting, yet incorporating dozens of antique fixtures and features to remind you this was a very old building. We were literally amazed and totally impressed. We sent pictures to all of...
The price is CA $299
CA $469 total
includes taxes & fees
Jun 9 - Jun 10
⭐️⭐️ theLOFTonJAMES ⭐️⭐️
Afan Home of Joy
9.8 out of 10, Exceptional, 7 reviews
"Wonderful property, will definitely recommend"
The price is CA $85
CA $170 total
includes taxes & fees
Jun 10 - Jun 11
Afan Home of Joy
King Bed Astounding Cinematic Sunset in trendy location, South City
10.0 out of 10, Exceptional, 30 reviews
"A great homebase for Winnipeg vacation. Well equipped and well appointed home."
King Bed Astounding Cinematic Sunset in trendy location, South City
Oceanfront 4th Floor, 2 Bedroom Condo on the Boardwalk!
9.2 out of 10, Wonderful, 44 reviews
"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!
Luxurious House in a Desired Location, King Bed
10.0 out of 10, Exceptional, 19 reviews
"Beautiful home, all you need for cooking, including bbq on deck. Host is responsive and provides key info required for an excellent experience. Really close to any amenity you need and minutes from major artery to get where you need to go. Overall, a great stay, highly recommend."
Luxurious House in a Desired Location, King Bed
Don't see what you're looking for?
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 Vacation 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, 1,012 reviews
"We booked last minute to avoid a late night 3.5 hour drive home in the rain. The service was good, staff was pleasant late at night and there were cold drinks at reception and a complimentary tube of toothpaste once I realized I had forgotten ours. The beds were comfortable, room was clean. Great place to wait out the night coming or going from Winnipeg for out of towners. "
The price is CA $140
CA $157 total
includes taxes & fees
Jun 30 - Jul 1
Motel 6 Headingley, MB - Winnipeg West
Best Western Plus Winnipeg West
2.5 star property
8.8 out of 10, Excellent, 1,005 reviews
"We came for a soccer tournament and it was so close and convenient! "
The price is CA $164
CA $183 total
includes taxes & fees
Jun 23 - Jun 24
Best Western Plus Winnipeg West
Victoria Inn Hotel and Convention Centre Winnipeg
3.0 star property
8.4 out of 10, Very good, 1,401 reviews
"I enjoyed everything about the hotel, except seeing intoxicated guessed which i know you can't actually control. "
The price is CA $185
CA $219 total
includes taxes & fees
Jun 16 - Jun 17
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Headingley?

Yes, you can find vacation rentals in Headingley close to BellMTS Iceplex, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Headingley has a good selection of coffeehouses. Make sure you have time to check out the hockey games and riverfront during your trip.

What are some of the best vacation rentals in Headingley?

Luxurious and Comfortable 3-Bedroom Bungalow Style House: This vacation 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 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 vacation rentals like in Headingley?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Headingley. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.

Recent reviews of Headingley properties
Expedia verified reviews