Headingley Vacation Rentals

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Vacation Rentals in Headingley

Dining
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
9.6 out of 10, Exceptional, (8)
"Good location to stay"
United States
Sarah
$109 nightly
The price is $128
Oct 20 - Oct 21
Total with taxes and fees
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
1 bedroom, iron/ironing board, free WiFi, bed sheets
Morning glory cottage
Morning glory cottage
8.8 out of 10, Excellent, (38)
"Good place "
United States
Roy H.
$73 nightly
The price is $85
Nov 5 - Nov 6
Total with taxes and fees
Morning glory cottage
Smart TV
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre
10.0 out of 10, Exceptional, (7)
"We stayed here for a few days and really enjoyed it. The old time freight elevator at the back entrance was so cool to ride in!"
Canada
Jennifer D.
$225 nightly
The price is $265
Oct 19 - Oct 20
Total with taxes and fees
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre
Exterior detail
Afan Home of Joy
Afan Home of Joy
9.6 out of 10, Exceptional, (21)
"We had an enjoyable stay, the place was clean and spacious with all the facilities and the host were great!We will definitely rent it again next time to come to Winnipeg. "
Canada
nayetc
$105 nightly
The price is $123
Oct 29 - Oct 30
Total with taxes and fees
Afan Home of Joy
Exterior
Luxury skyline entire condo in downtown with FREE 24/7 parking
Luxury skyline entire condo in downtown with FREE 24/7 parking
9.6 out of 10, Exceptional, (18)
"Great location. We enjoyed our 4 night stay!"
Canada
David
Luxury skyline entire condo in downtown with FREE 24/7 parking
Fridge, microwave, oven, stovetop
Home Away from Home! Family-sized vacations, group getaways, business trips,
Home Away from Home! Family-sized vacations, group getaways, business trips,
9.4 out of 10, Exceptional, (8)
"It was supplied all essential needs. It was in an excellent neighborhood. The place was clean and welcoming. Felt like home as we were evacuated from our placement in Flin Flon, Manitoba."
Canada
Annette P.
Home Away from Home! Family-sized vacations, group getaways, business trips,
Smart TV
2 Br/ 3 beds with free parking, wifi and much more
2 Br/ 3 beds with free parking, wifi and much more
9.2 out of 10, Wonderful, (26)
"Great location in a heritage building, comfortable and clean."
Canada
Marlena W.
2 Br/ 3 beds with free parking, wifi and much more
Outdoor dining
Maryland Homestay - Downtown Apartment
Maryland Homestay - Downtown Apartment
6.0 out of 10, (1)
$113 nightly
The price is $132
Oct 29 - Oct 30
Total with taxes and fees
Maryland Homestay - Downtown Apartment
Pool
The Wooden Nest | Your Comfy Relaxing Escape
The Wooden Nest | Your Comfy Relaxing Escape
10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. It had everything we needed and was close to amenities. The host was very response with all questions Would definitely book again."
Canada
Linda L.
$183 nightly
The price is $205
Oct 22 - Oct 23
Total with taxes and fees
The Wooden Nest | Your Comfy Relaxing Escape
Dining
FREE PARKING NY Style Condo in Exchange District
FREE PARKING NY Style Condo in Exchange District
10.0 out of 10, Exceptional, (66)
"Beautiful condo, tastefully decorated and very comfortable "
Canada
Theresa B.
$128 nightly
The price is $150
Oct 20 - Oct 21
Total with taxes and fees
FREE PARKING NY Style Condo in Exchange District
Fridge, microwave, stovetop, coffee/tea maker
Cozy Home away from Home in a Basement with a separate entrance
Cozy Home away from Home in a Basement with a separate entrance
9.8 out of 10, Exceptional, (8)
"Great location, easy access, everything you need."
Canada
Tony M.
$120 nightly
The price is $140
Oct 20 - Oct 21
Total with taxes and fees
Cozy Home away from Home in a Basement with a separate entrance
Exterior
🌎Modern 3 bedroom home w/street park’n close to ✈️
🌎Modern 3 bedroom home w/street park’n close to ✈️
10.0 out of 10, Exceptional, (3)
"This property is beautiful. The owner is top hostess she went above and beyond for us. Will definitely being staying here again"
Canada
Aldeana L.
$451 nightly
The price is $530
Oct 20 - Oct 21
Total with taxes and fees
🌎Modern 3 bedroom home w/street park’n close to ✈️
Exterior detail
Fully Furnished Basement Unit – Private Entrance Included
Fully Furnished Basement Unit – Private Entrance Included
9.0 out of 10, Wonderful, (4)
"Nice place "
Canada
hanad m.
$88 nightly
The price is $102
Oct 29 - Oct 30
Total with taxes and fees
Fully Furnished Basement Unit – Private Entrance Included
Smart TV, fireplace, foosball, books
Cheerful Tuxedo House with Hot Tub
Cheerful Tuxedo House with Hot Tub
9.8 out of 10, Exceptional, (21)
"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"
Canada
Mike
$467 nightly
The price is $548
Oct 22 - Oct 23
Total with taxes and fees
Cheerful Tuxedo House with Hot Tub
Terrace/patio
Full house in the best neighborhood of Winnipeg-Bridgwater Forest
Full house in the best neighborhood of Winnipeg-Bridgwater Forest
6.0 out of 10, (6)
"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 "
United States
Erik S.
$107 nightly
The price is $126
Oct 29 - Oct 30
Total with taxes and fees
Full house in the best neighborhood of Winnipeg-Bridgwater Forest
Fridge, microwave, oven, stovetop
Flamingo Home! A family-friendly home with 4 bedrooms and 3 bathrooms.
Flamingo Home! A family-friendly home with 4 bedrooms and 3 bathrooms.
9.0 out of 10, Wonderful, (13)
"Amazing home, host, neighborhood! Spacious, clean and lovely-absolutely loved staying here with my family!"
United States
Roxanne M.
Flamingo Home! A family-friendly home with 4 bedrooms and 3 bathrooms.
Exterior detail
Private Cozy 1 Bedroom Basement Suite
Private Cozy 1 Bedroom Basement Suite
10.0 out of 10, Exceptional, (3)
"Nice clean place to stay"
United States
Thomas B.
$105 nightly
The price is $123
Oct 29 - Oct 30
Total with taxes and fees
Private Cozy 1 Bedroom Basement Suite
Pool
Trendy & Central | New Home
Trendy & Central | New Home
10.0 out of 10, Exceptional, (1)
$181 nightly
The price is $203
Oct 29 - Oct 30
Total with taxes and fees
Trendy & Central | New Home
2 bedrooms, WiFi, bed sheets
Suite with facilities to make you feel at home
Suite with facilities to make you feel at home
$9,422 nightly
The price is $11,092
Oct 20 - Oct 21
Total with taxes and fees
Suite with facilities to make you feel at home
Outdoor dining
Maryland Homestay - Downtown Apartment
Maryland Homestay - Downtown Apartment
6.0 out of 10, (4)
"It should state there are just two rooms and the kitchen, location was good everything was walking distance. Was ok for our first time. "
Canada
Jessica M.
$113 nightly
The price is $132
Oct 20 - Oct 21
Total with taxes and fees
Maryland Homestay - Downtown Apartment
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

Sandman Signature Winnipeg Airport Hotel & Suites

Sandman Signature Winnipeg Airport Hotel & Suites

10/10 Excellent
"Great hotel! Kids loved pool and water slide"
Shauna 2-night trip
Posted 2 days ago
Sandman Signature Winnipeg Airport Hotel & Suites

Find out more about Headingley

Everything you need to know about Headingley vacation rentals

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

Headingley vacation 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 low season months. For more hustle and bustle, you may prefer to visit Headingley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $85 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Headingley rentals

At Expedia, we put the best Headingley vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Morning glory cottage: This vacation home rental outside of Headingley has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

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 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.