Holiday Rentals Headingley from £84: Find Short-Term Rentals & Holiday Accommodations

Q: What are some of the best holiday rentals that Headingley has to offer?

Brilliant 4-bedroom house with AC in Winnipeg : This holiday home rental outside of Headingley offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

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In two weeks

In two months

In three months

In four months

Our top choices for Headingley holiday rentals

Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi

Transcona

includes taxes & fees

13 Jul - 14 Jul

Spacious & cozy family/group-sized home with backyard, deck & Gazebo!

Transcona

includes taxes & fees

4 Aug - 5 Aug

Luxury: Home Away from Home with Private Entrance

Transcona

Owen

includes taxes & fees

20 Jul - 21 Jul

Entire Guest Suite/Separate Entrance/Free Parking in Winnipeg

Transcona

Priscilla N.

includes taxes & fees

23 Jul - 24 Jul

Furnished basement with seperate entrance ,living room,washroom and kitchenette

Transcona

includes taxes & fees

11 Jul - 12 Jul

Royal Oak - 2-bedroom (King & Queen bed), Living Area, Kitchen and Full bathroom

Peguis

includes taxes & fees

8 Aug - 9 Aug

Cozy 1-Bedroom Private Basement Suite in Winnipeg. Separate Entrance.

Peguis

Robert L.

includes taxes & fees

8 Aug - 9 Aug

Blissful 2 bedroom basement in Winnipeg with Wifi, AC

Peguis

William M.

includes taxes & fees

12 Jul - 13 Jul

Family suit near costco with free parking and wifi

Peguis

includes taxes & fees

29 Jul - 30 Jul

Cozy 3-Bedroom Basement Suite with Private Entrance

Transcona

"The unit itself was very nice. Clean and well stocked for needs. Was advertised as a three bedroom but only two of them were accessible. Not sure why one bedroom was locked. Overall a nice place but one issue was the people upstairs must have had company and were extremely loud. A couple mornings there was a lot of stomping around at 6am. So the sound proofing between upstairs and downstairs isn’t great. Even so, I would still consider staying here again. Host was very quick in responding to...

Kyle M.

includes taxes & fees

13 Jul - 14 Jul

Afan Home of Joy (Private Entrance)

Peguis

Graham J.

includes taxes & fees

13 Jul - 14 Jul

Cozy 1BR Suite + Sitting Room | Quick Access to Regent East

Transcona

"The place was clean, host was very nice. There was some small things that didn’t go as planned. One was that there is a family living upstairs but they were quiet for the most part, they were loud sometimes but not too bad. There was a kid that came downstairs and opened the bedroom door while we were sleeping but the host took care of it quickly. They also only put three forks when there were four of us staying and other small things like that. Overall very nice place and would definitely stay...

Maddix

includes taxes & fees

10 Jul - 11 Jul

Cozy Nest - 1 Bedroom

St. Vital

includes taxes & fees

20 Jul - 21 Jul

Warm, Inviting Basement Suite • Quiet Stay in a Safe, Upscale Area

St. Vital

" Exceptional Stay – A True Home Away From HomeI had an outstanding stay at this beautiful B&B and would highly recommend it to anyone traveling for business or pleasure.The apartment was exceptionally clean, well-maintained, and thoughtfully equipped with everything I could possibly need. From the moment I arrived, it felt more like a home than a rental. Rachel has clearly put a great deal of thought into ensuring her guests are comfortable, providing not only all the necessities but also many...

marta s.

includes taxes & fees

8 Aug - 9 Aug

Golden Eagle, Basement Suite

Winnipeg

Simran K.

includes taxes & fees

22 Jul - 23 Jul

Morning glory cottage

Peguis

Caleb

Embassy Suites.

Peguis

Shastina

The perfect Retreat

Peguis

Erik

Cozy 1-bedroom with King size bed

Winnipeg

"The price was right. It looks ok until you started to look closer at the room. Things were not clean. The bed mattress was flat from people and smells . No top sheet. And the bed cover was dirty. The pillows smells. Did not use them. I was supposed to get a lock code and was not giving. No lock key for my room to lock up my things when I went out and was locked out two times from the house. I feel like a prisoner . No wifi was not giving a password also. And yes I asked for the door lock...

Lydia

includes taxes & fees

8 Aug - 9 Aug

Cozy Winnipeg Retreat

Peguis

Jaymee

includes taxes & fees

16 Jul - 17 Jul

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Top Headingley Hotel Reviews

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic 3 night stay in a spacious suite with a downtown view. Traveling with our dogs so we used room service from the Oval Room on a couple evening meals, they were delicious and fairly priced. The staff are friendly and helpful. The hotel is beautiful and with lots of walking opportunities. We enjoyed our stay very much and plan to return for more exploration. There is so much to see, I highly recommend The beautiful Fort Garry Hotel."

Comfort Inn South

10/10 Excellent

"We had a great stay! Gerald in reception was very welcoming and a very bubbly person, The room was very clean and the AC was blowing very cold which was a welcome feature during the hot Winnipeg summer. The breakfast was also good with a good selection of breads pancakes and beverages. All in all a great value for our money and will definitely consider staying there again for a staycation."

Find out more about Headingley

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, apart-hotels, 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 favorite 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 depends 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 £84 per night. Entering your travel dates in the search wizard you might find 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 Thunder Rapids Fun Park, 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?

Brilliant 4-bedroom house with AC in Winnipeg: This holiday home rental outside of Headingley offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that 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 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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Check prices for these dates

Our top choices for Headingley holiday rentals

Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi

Spacious & cozy family/group-sized home with backyard, deck & Gazebo!

Luxury: Home Away from Home with Private Entrance

Entire Guest Suite/Separate Entrance/Free Parking in Winnipeg

Furnished basement with seperate entrance ,living room,washroom and kitchenette

Royal Oak - 2-bedroom (King & Queen bed), Living Area, Kitchen and Full bathroom

Cozy 1-Bedroom Private Basement Suite in Winnipeg. Separate Entrance.

Blissful 2 bedroom basement in Winnipeg with Wifi, AC

Family suit near costco with free parking and wifi