Headingley Vacation Rentals

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Check prices for these dates

Tonight
Jul 27 - Jul 28
Tomorrow
Jul 28 - Jul 29
Next weekend
Aug 1 - Aug 3
In two weeks
Aug 8 - Aug 10

Vacation Rentals in Headingley

Cheerful Tuxedo House with Hot Tub
Relax in this inviting living space with comfortable seating and a stylish coffee table.

Cheerful Tuxedo House with Hot Tub

9.8 out of 10, Exceptional, (13)
"Fantastic place. Plenty of room, comfortable beds and great neighborhood. Hot tub was a perfect way to end the day. I’d definitely stay here again next time"
Cheerful Tuxedo House with Hot Tub
Full house in the best neighborhood of Winnipeg-Bridgwater Forest
Relax on the balcony with a sofa, table, and lush greenery, taking in the views of the water and surrounding buildings.

Full house in the best neighborhood of Winnipeg-Bridgwater Forest

7.4 out of 10, Good, (3)
"Property was as advertised. Second bed was more of a thick foam pad. Fine for a few nights. Would recommend and stay there again. Fantastic location easy access to everything we needed "
$120 nightly
The price is $140
Aug 5 - Aug 6
Total includes taxes and fees
Full house in the best neighborhood of Winnipeg-Bridgwater Forest
2500 sq ft 5 beds 3.5 bath New Home (2021)
Interior

2500 sq ft 5 beds 3.5 bath New Home (2021)

9.4 out of 10, Exceptional, (23)
"It is a nice place with a lot of rooms for a large group of people. We were 8 adults and all enjoyed the stay. "
$188 nightly
The price is $220
Aug 6 - Aug 7
Total includes taxes and fees
2500 sq ft 5 beds 3.5 bath New Home (2021)
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
Enjoy meals in the kitchen area with a dining space, featuring a refrigerator, microwave, and sink.

2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.

9.6 out of 10, Exceptional, (5)
"Super friendly people, fantastic place as was perfect for what we wanted and had many little extras. Would definitely try to get this place again if need a place to stay in the future "
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
Afan Home of Joy
Secure entrance with a modern door and clean design.

Afan Home of Joy

9.6 out of 10, Exceptional, (16)
"We enjoyed our 4-day stay, it was very clean, in a new home, quiet and spacious, and our hosts were very accomodating."
$107 nightly
The price is $125
Jul 28 - Jul 29
Total includes taxes and fees
Afan Home of Joy
2 Br/ 3 beds with free parking, wifi and much more
Relax in this inviting space with a flat-screen TV, comfortable sofa, and a dining area just beyond the glass door.

2 Br/ 3 beds with free parking, wifi and much more

9.4 out of 10, Exceptional, (19)
"Great over all location"
2 Br/ 3 beds with free parking, wifi and much more
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre
Cozy living space with a brick wall, large window, and comfortable couch.

Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre

10.0 out of 10, Exceptional, (5)
"Great proximity to nice restaurants"
$230 nightly
The price is $271
Aug 2 - Aug 3
Total includes taxes and fees
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre
Welcoming Private 2 Bedroom Suite
Stroll up the staircase to the deck, surrounded by an outdoor space with a water feature and scenic views.

Welcoming Private 2 Bedroom Suite

9.4 out of 10, Exceptional, (6)
"Fantastic property, excellent hosts! The beds were super comfy, everything we needed was accessible, and the place is in a fantastic location. Would definitely stay again, and highly recommend!"
$107 nightly
The price is $126
Jul 30 - Jul 31
Total includes taxes and fees
Welcoming Private 2 Bedroom Suite
(1703)Downtown Glasshouse Sophisticated 2BR1BATH +Fast WiFi(311)
Enjoy meals and socialize at the central island with seating for three.

(1703)Downtown Glasshouse Sophisticated 2BR1BATH +Fast WiFi(311)

8.8 out of 10, Excellent, (8)
"Great location, good service and support!"
(1703)Downtown Glasshouse Sophisticated 2BR1BATH +Fast WiFi(311)
FREE PARKING NY Style Condo in Exchange District
Experience communal dining and meetings in this spacious, open-plan area with metal beams, glass roof, and modern lighting fixtures.

FREE PARKING NY Style Condo in Exchange District

10.0 out of 10, Exceptional, (60)
"Beautiful condo, tastefully decorated and very comfortable "
$138 nightly
The price is $162
Aug 10 - Aug 11
Total includes taxes and fees
FREE PARKING NY Style Condo in Exchange District
Cozy 3BR near Airport/DTown/Mall
Enjoy cooking in this well-equipped kitchen with a microwave, refrigerator, and sink.

Cozy 3BR near Airport/DTown/Mall

9.2 out of 10, Wonderful, (15)
"Great place to stay. Nice to have the whole home to yourself. Check in and checkout were very easy. "
$220 nightly
The price is $258
Aug 3 - Aug 4
Total includes taxes and fees
Cozy 3BR near Airport/DTown/Mall
Cozy Home away from Home in a Basement with a separate entrance
Enjoy cooking in this well-equipped kitchen with a microwave, refrigerator, sink, and ample countertop space.

Cozy Home away from Home in a Basement with a separate entrance

10.0 out of 10, Exceptional, (5)
"My wife and I stayed in Winnipeg for a few nights in Dec 2022. The suite was easily accessible, located in the lower level of a house in a residential neighborhood. Was refreshing to get away from 'corporate' for a bit. Bed was comfortable and everything that we needed was provided - even creamers for the coffee. We didn't use the TV, but apparently it has several thousand channels so you can surf to your heart's content. The host, Christiana, was very attentive and made sure we had all that we...
$96 nightly
The price is $112
Jul 31 - Aug 1
Total includes taxes and fees
Cozy Home away from Home in a Basement with a separate entrance
King Bed Astounding Cinematic Sunset in trendy location, South City
Relax in a serene hot tub surrounded by a tranquil wooded area.

King Bed Astounding Cinematic Sunset in trendy location, South City

10.0 out of 10, Exceptional, (44)
"Great stay. "
$342 nightly
The price is $402
Aug 4 - Aug 5
Total includes taxes and fees
King Bed Astounding Cinematic Sunset in trendy location, South City
Rare*Full Home in Downtown Winnipeg|Free Parking
Enjoy cooking and dining in this well-equipped kitchen with a spacious island, sink, and ample seating.

Rare*Full Home in Downtown Winnipeg|Free Parking

9.8 out of 10, Exceptional, (19)
"My family and I spent a wonderful 10 days. We were very comfortable and the location cannot be beat."
Rare*Full Home in Downtown Winnipeg|Free Parking
Kelvista's suite
Fully equipped kitchen with integrated appliances, coffee maker, kettle, toaster, and sink.

Kelvista's suite

9.6 out of 10, Exceptional, (5)
"This property was amazing would love to stay here again "
$107 nightly
The price is $126
Aug 11 - Aug 12
Total includes taxes and fees
Kelvista's suite
Spacious 2 BR 1 BATH - NEAR DOWNTOWN
Stunning two-story home with a central bay window and well-manicured surroundings.

Spacious 2 BR 1 BATH - NEAR DOWNTOWN

$275 nightly
The price is $323
Aug 17 - Aug 18
Total includes taxes and fees
Spacious 2 BR 1 BATH - NEAR DOWNTOWN
Winnipeg Radiant Home - A peaceful neighborhood with separate entrance
Stroll along the winding pathway to a charming wooden staircase.

Winnipeg Radiant Home - A peaceful neighborhood with separate entrance

8.8 out of 10, Excellent, (3)
"The suite was located on a quiet street but close to a main street so it was easy getting around. It was sparsely furnished and could have used extra bath towels, face clothes, and blankets. The floor under the bed needs be to be thoroughly cleaned. Considering the affordable cost, it was a good value overall."
$74 nightly
The price is $87
Aug 3 - Aug 4
Total includes taxes and fees
Winnipeg Radiant Home - A peaceful neighborhood with separate entrance
Executive Luxury 2 bed Spacious Downtown WIFI laundry
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, white cabinetry, and a large window offering a city view.

Executive Luxury 2 bed Spacious Downtown WIFI laundry

7.4 out of 10, Good, (13)
"Communication was spotty - similar to other reviews. Good location, apartment was nice and fairly clean. "
Executive Luxury 2 bed Spacious Downtown WIFI laundry
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!
Relax in this stylish living room with a large window offering a view of the surrounding area, a flat-screen TV, and a comfortable sofa.

NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!

10.0 out of 10, Exceptional, (64)
"Very nice apartment. Great location and the parking garage was very nice!"
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!
Luxury 2 bed 2 bath across jets arena 16th floor with amazing view
Enjoy expansive city views from the large windows in this stylish living area with a sofa, armchairs, and dining table.

Luxury 2 bed 2 bath across jets arena 16th floor with amazing view

8.0 out of 10, Very Good, (36)
"Would stay again "
Luxury 2 bed 2 bath across jets arena 16th floor with amazing view
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.
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Top Headingley Hotel Reviews

Radisson Hotel Winnipeg Downtown

Radisson Hotel Winnipeg Downtown

10/10 Excellent
"Enjoyed our stay"
T 2-night trip
Posted 18 hours ago
Radisson Hotel Winnipeg Downtown

Frequently asked questions

Can I find a vacation rental in Headingley?

Yes, you can find vacation rentals in Headingley close to Thunder Rapids Fun Park, 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?

Cheerful Tuxedo House with Hot Tub : This vacation home rental outside of Headingley offers a fireplace, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Headingley?

While exploring the area, visit family-friendly sights like Thunder Rapids Fun Park, or get outside and enjoy nature at Assiniboine Park. While here, John Blumberg Softball Complex and Beaudry Provincial Park 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.