Photo by Tourism Winnipeg/Dan Harper

Winnipeg Holiday Rentals

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Holiday Rentals in Winnipeg

FREE PARKING NY Style Condo in Exchange District

Exchange District
10.0 out of 10, Exceptional, (71)
"Neat and tidy; well appointed; very comfortable; lovely location"
Canada
Maryke W.
The price is AU$243
includes taxes & fees
16 Dec - 17 Dec
FREE PARKING NY Style Condo in Exchange District

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

Osborne Village
10.0 out of 10, Exceptional, (76)
"Very nice condo in a great location. We really enjoyed our stay here during a short family vacation. "
Canada
Jacob
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!

Fully Furnished Basement Unit – Private Entrance Included

St. Vital
8.4 out of 10, Very good, (7)
"Well maintained and very clean."
Canada
Calvin G.
The price is AU$159
includes taxes & fees
7 Dec - 8 Dec
Fully Furnished Basement Unit – Private Entrance Included

Morning glory cottage

Peguis
8.6 out of 10, Excellent, (40)
"Good place "
United States
Roy H.
The price is AU$133
includes taxes & fees
16 Dec - 17 Dec
Morning glory cottage

3 floors character house

Winnipeg
9.6 out of 10, Exceptional, (73)
"Got everything you need for your stay in Winnipeg and can’t beat the price! "
Canada
Francois C.
3 floors character house

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

Exchange District
9.4 out of 10, Exceptional, (10)
"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.
The price is AU$436
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre

St B. Living

Central St. Boniface
9.6 out of 10, Exceptional, (16)
"Very clean rental. Easy to access and property owner was very responsive. "
United States
Jill F.
The price is AU$200
includes taxes & fees
16 Dec - 17 Dec
St B. Living

The perfect Retreat

Peguis
8.4 out of 10, Very good, (5)
"Owner was very friendly and house was well maintained "
Canada
Erik
The price is AU$132
includes taxes & fees
11 Dec - 12 Dec
The perfect Retreat

Afan Home of Joy

Peguis
9.6 out of 10, Exceptional, (22)
"Hosts very friendly, good location!"
Canada
Chris K.
The price is AU$190
includes taxes & fees
16 Dec - 17 Dec
Afan Home of Joy

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

Transcona
9.6 out of 10, Exceptional, (10)
"Good location to stay"
United States
Sarah
The price is AU$185
includes taxes & fees
6 Dec - 7 Dec
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.

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

St. Vital
9.2 out of 10, Wonderful, (10)
"The place is clean, cozy and affordable. The accommodations were spot on accurate and the host Christiana answered any questions quickly. I would recommend this location to travelers."
United States
Charles
The price is AU$217
includes taxes & fees
7 Dec - 8 Dec
Cozy Home away from Home in a Basement with a separate entrance

🌎Modern 3 bedroom home w/street park’n close to ✈️

Weston
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.
The price is AU$816
includes taxes & fees
16 Dec - 17 Dec
🌎Modern 3 bedroom home w/street park’n close to ✈️

theLOFTonJAMES, Historic Exchange District, Exposed Brick & Beams, High Ceilings

Exchange District
10.0 out of 10, Exceptional, (61)
"The place was very nice and clean. It’s in a great location near restaurants and bars."
United States
Steve M.
The price is AU$570
includes taxes & fees
7 Dec - 8 Dec
theLOFTonJAMES, Historic Exchange District, Exposed Brick & Beams, High Ceilings

Kelvista's suite

St. Vital
9.4 out of 10, Exceptional, (10)
"A comfortable and affordable place to stay! The host is great with communication and the suite is lovely!"
Canada
Laura
The price is AU$204
includes taxes & fees
2 Jan - 3 Jan 2026
Kelvista's suite

*Spacious w/ Style | Free Parking | 7 min Airport*

King Edward
9.4 out of 10, Exceptional, (6)
"Great place with a great location, lots of things in walking distance. "
United States
Tyler s.
The price is AU$312
includes taxes & fees
8 Dec - 9 Dec
*Spacious w/ Style | Free Parking | 7 min Airport*

Private Basement Apartment with separate entrance

St. Vital
10.0 out of 10, Exceptional, (1)
"Perfect for a 1 night stay. Just passing through. "
Canada
Norman
The price is AU$171
includes taxes & fees
9 Dec - 10 Dec
Private Basement Apartment with separate entrance

Golden Eagle, Basement Suite

Winnipeg
10.0 out of 10, Exceptional, (1)
"Very clean and as advertised. Beds were very comfortable."
Canada
Harold
The price is AU$176
includes taxes & fees
10 Dec - 11 Dec
Golden Eagle, Basement Suite

Chesskings Guest House - Unit 2 Notredame Avenue

West Alexander
2.0 out of 10, (2)
"They cancelled on me the day i was spose to check in so i dont recommended anyone staying here ever!!!"
Canada
Rick .j.
The price is AU$164
includes taxes & fees
16 Dec - 17 Dec
Chesskings Guest House - Unit 2 Notredame Avenue

Prairie Luxury 2 Bedrooms Home

Fort Garry
9.2 out of 10, Wonderful, (5)
"Great space. Host was very responsive to our requests."
Canada
Bels45
The price is AU$335
includes taxes & fees
5 Jan - 6 Jan 2026
Prairie Luxury 2 Bedrooms Home

Cheerful Tuxedo House with Hot Tub

Tuxedo
9.8 out of 10, Exceptional, (28)
"Amazing stay, beautiful area, house had everything you need and more! "
United States
Ashley and H.
The price is AU$1,097
includes taxes & fees
16 Dec - 17 Dec
Cheerful Tuxedo House with Hot Tub
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 Winnipeg Hotel Reviews

Find out more about Winnipeg

Everything you need to know about Winnipeg 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 Winnipeg 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 Winnipeg holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winnipeg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winnipeg. 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 Winnipeg 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 Winnipeg holiday rentals we have selected for you start as low as AU$132 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winnipeg rentals

At Expedia, we put the best Winnipeg 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 Winnipeg 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 Winnipeg 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 Winnipeg. 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 holiday rentals in Winnipeg?

Yes, there are holiday rentals in Winnipeg close to Assiniboine Park Zoo, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and scenic riverfront in Winnipeg. The fascinating museums and entertainment choices are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Winnipeg has to offer?

Morning glory cottage: This highly rated holiday home rental in Winnipeg 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. Other favourite homes for rent in Winnipeg are Afan Home of Joy and 3 floors character house.

How many holiday rentals are there in Winnipeg?

Expedia has 271 holiday rentals for your stay in Winnipeg.

What can I see and do in Winnipeg?

Assiniboine Park Zoo and BellMTS Iceplex are a couple of the family-friendly sights, whereas cultural attractions include Canadian Museum for Human Rights and Burton Cummings Theatre. While here, Thermëa - Winnipeg and St. Vital Centre are other places worth a visit.

What are holiday rentals like in Winnipeg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winnipeg. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to 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 great choice for family trips or small group gatherings.