House Sitting in Headingley

Find a loving house sitter to watch over your pets and your home.

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Top rated Headingley house sitters

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Kristin C.
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Kristin C.
Star Sitter
$50
total per night
5.0 out of 5 stars
32 reviews
12 repeat clients
15 years of experience
Winnipeg, MB, R2Y

We loved having Kristin dog-sit for us! Kristin truly went above & beyond from buying our dog Odin a special toy to cleaning our oven! It made our holiday even more enjoyable having the peace of mind that Odin & our home were being so well looked after!

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Darryl F.
Sitter Profile Image: Rp S.
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Rp S.
$45
total per night
5.0 out of 5 stars
91 reviews
28 repeat clients
24 years of experience
Winnipeg, MB, R2L

Rp is truly a one of a kind dog sitter. This is our 3rd booking with Rp. We trust him and know that our 3 fur babies are in great hands while we are away. It is also nice to come home to a clean house. Thank you Rp, for your outstanding service, we are very grateful we found you!

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Caley O.
Sitter Profile Image: Amanda B.
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Amanda B.
$45
total per night
24 years of experience
Winnipeg, MB, R3J

About: I have taken care of animals since I can remember. Between caring for my dogs and cat at home or my grandma’s horses, I have always been around animals. As my dog is high energy, I have taken numerous courses on how to help train and guide her through life. These courses has extended my knowledge on how to take care of dogs and love them even more! I am currently working full time and in school however, due to the flexibility in my schedule, I am able to take care of your furry loved ones round the clock! I am able to adapt to your routine to make sure that your pet(s) aren’t thrown off by a new routine created by a new person. This allows for a smoother transition while you are away. I am also comfortable walking dogs of all ages and reactivity as I have well versed experience with reactive dogs.

Sitter Profile Image: Chloe B.
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Chloe B.
$45
total per night
10 years of experience
Winnipeg, MB, R3K

About: I’ve grown up with dogs my whole life and currently own two — one big and one small — and have also worked with dogs, which has strengthened my confidence handling different breeds, personalities, and energy levels. I truly treat every pet like my own and take the time to understand their unique needs, whether they’re energetic puppies who love playtime or calmer seniors who prefer a slower pace. I’m patient, attentive, and very mindful of keeping pets on their normal routines to help them feel comfortable and secure. My goal is always to create a safe, loving, and stress-free environment while you’re away. I’m reliable, communicative, and happy to provide regular photo updates so you can feel completely at ease knowing your pet is in caring hands. Pet care fits naturally into my daily routine, as I already care for my own dogs every day. I have a flexible schedule and can easily plan my days around walks, feeding times, playtime, and check-ins to ensure your pet gets consistent attention and care. Safety and trust are my top priorities when caring for pets in their own home. I carefully follow all instructions regarding feeding, walks, medications, and routines to ensure your pet feels comfortable and secure. I’m very mindful of keeping doors and gates secure during visits and use safe, attentive leash handling on walks. I respect your home as if it were my own and make sure everything is left clean and exactly as I found it. My goal is to provide dependable, stress-free care so both you and your pet feel completely at ease.

Sitter Profile Image: Shayleece R.
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Shayleece R.
$45
total per night
5.0 out of 5 stars
7 reviews
3 repeat clients
10 years of experience
Winnipeg, MB, R2Y

Another fantastic job. Really took care of my dog like he was hers. Communication was good. Even though I was several time zones away. Always ready to do right by my dog. If you really want someone that will care for your pet and has great communication skills, Shayleece is fantastic.

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Aaron S.
Sitter Profile Image: Orin T.
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Orin T.
$48
total per night
4.3 out of 5 stars
11 reviews
1 repeat client
3 years of experience
Winnipeg, MB, R3K

About: Dog lover with 3+ years of hands-on experience, including raising my own from puppyhood. Calm, caring, and reliable — your pup will feel right at home with me! I'm available throughout the week with at least one day’s notice. Pet care fits easily into my routine, and I always make time to give each pet the love and attention they deserve. I offer a calm, pet-friendly home in a quiet neighborhood with a secure backyard for safe outdoor play and relaxation. Pets are always supervised and cared for with love and attention. I stick to their routine, provide a clean and cozy environment, and make sure they feel safe, relaxed, and at home.

Sitter Profile Image: Ruth M.
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Ruth M.
$56
total per night
5.0 out of 5 stars
8 reviews
3 repeat clients
20 years of experience
Winnipeg, MB, R3J

Ruth was absolutely amazing!! She sent constant pictures of our girls and kept us in the loop if anything happened! We will definitely be rebooking with her🥰 highly recommend to anyone looking to book!

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CherryFox08
Sitter Profile Image: Christina R.
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Christina R.
$45
total per night
60 years of experience
Winnipeg, MB, R3E

About: Retired Senior lady looking to add more love into her life. I have 4 pets of my own & I want to love your pets too. Im available 24/7. After waking up whatever fur baby is in bed with me, I will let them outside for potty & then get their breakfast ready. I like to watch from a window or be outside with the fur babies when they are on their potty break. Their safety is paramount.

Sitter Profile Image: Ranchelle O.
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Ranchelle O.
Star Sitter
$45
total per night
4.9 out of 5 stars
64 reviews
26 repeat clients
12 years of experience
Winnipeg, MB, R2R

Excellent care taken. My dog was well looked after and pretty happy with the whole experience. Lots of photos and videos taken.

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Aaron S.
Sitter Profile Image: Mariah L.
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Mariah L.
$67
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
20 years of experience
Winnipeg, MB, R2R

Mariah looked after our cat and dog while we were away for 2 weeks. She does an excellent job of caring for our pets and house sitting. Her photos of our pets that she sent to us are also excellent! We've hired her twice now and she'll be our go to for any future trips we have.

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Kaitie R.
Sitter Profile Image: Ruth K.
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Ruth K.
$56
total per night
13 years of experience
Winnipeg, MB, R2Y

About: Passionate and caring individual who loves animals. I have been taking care of my dog for the past 13 years and had to put her down and had 4 cats. Flexible before work hours and after work hours. Work hours are from 8-4 pm but mainly work from home. I am free after work and free during the weekends as well. I had a fenced yard and had 4 pets, 3 cats and 1 dog and babysat 2 additional dogs. I provided care with proper hygiene, nutritious diet and regular exercises and maintained a clean and tidy environment. (Especially took my dog for car rides and to the park frequently)

Sitter Profile Image: Anna P.
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Anna P.
$28
total per night
5.0 out of 5 stars
2 reviews
14 years of experience
Winnipeg, MB, R3R

About: I had a Yorkie for 13 years before adopting my cat Pawl last year. I will be happy to take care of your babies too! I can do boarding for dogs only and drop-in visits for both cats and dogs. I work from home most days of the week and will also be happy to take care of your pet in the evenings and during weekends. I live in a house with a fenced yard and my indoor only cat is allowed anywhere he likes. My priority is your pet’s safety and happiness and your peace of mind. I will follow your care instructions and make sure to always keep you updated!

Sitter Profile Image: Memphis R.
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Memphis R.
$56
total per night
5.0 out of 5 stars
73 reviews
23 repeat clients
12 years of experience
Winnipeg, MB, R3L

We were very thankful to have Memphis stay in our house and watch our dog while we were away out of country. She kept us updated and sent pictures. We will definitely use Memphis' services again for future trips.

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Heidi L.
Sitter Profile Image: Jacob W.
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Jacob W.
$78
total per night
5.0 out of 5 stars
29 reviews
8 repeat clients
16 years of experience
Winnipeg, MB, R2M

Jacob did a great job with my babies. They really seemed to enjoy spending time with him. He communicated with me throughout the week sending me updates and pictures. I definitely would book with him again

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Kayla C.
Sitter Profile Image: Bethany B.
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Bethany B.
Star Sitter
$70
total per night
5.0 out of 5 stars
7 reviews
3 repeat clients
25 years of experience
Winnipeg, MB, R3M

Bethany was so great and accommodating. My plans ended up changing last minute due to weather and she was nothing but helpful. My fur babies loved her and she left my place looking perfect. I would definitely recommend her as a house and pet sitter.

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Katie W.
Sitter Profile Image: Natacha T.
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Natacha T.
Star Sitter
$73
total per night
5.0 out of 5 stars
57 reviews
17 repeat clients
20 years of experience
Winnipeg, MB, R3J

Natacha is an outstanding pet/house sitter. Very communicative, goes above and beyond in so many ways and most importantly really cares about the little animals. Highly recommend.

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Ian G.
Sitter Profile Image: Tanya G.
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Tanya G.
$56
total per night
5.0 out of 5 stars
1 review
15 years of experience
Winnipeg, MB, R3N

About: I have owned dogs, cats, and other animals in the past. I have also volunteered at veterinary clinic. I enjoy spending time animals and look forward to caring for yours. Let me know all the information I need to care for your pet(s). Can care for dogs that are house trained. I can care for dogs in my home and cats in yours. I enjoy spending time with animals and I look forward to hearing from you to care for your fur baby. I have considered my dogs to be a member of my family. I have a fenced back yard. I can care for dogs in my home and can pet sit cats in your home. I can offer drop in pet services also.

Sitter Profile Image: Michelle P.
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Michelle P.
$62
total per night
5.0 out of 5 stars
22 reviews
2 repeat clients
23 years of experience
Oak Bluff, MB, R0G

Michelle is an amazing pet sitter. We found her for a last-minute booking and couldn’t have been happier. She is friendly, responsible, and seems to love dogs as much as we do! Highly recommended.

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Karen B.
Sitter Profile Image: Erin B.
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Erin B.
$50
total per night
20 years of experience
Winnipeg, MB, R3Y

About: I have experience with small and big dogs! I have a chihuahua and a German shepherd! I enjoy taking them for walks and sniffing around the neighborhood I am currently available any day right now! I can administer medications! I have experience with big or small, high energy, timid and low energy! I will send you pictures everyday and I’m very good at following instructions that you give me before you go on your vacation! Thank you for trusting me!

Sitter Profile Image: Shawn B.
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Shawn B.
$45
total per night
5.0 out of 5 stars
2 reviews
1 repeat client
25 years of experience
Winnipeg, MB, R3M

About: I’ve taken care of pets my whole life. I have a passion for animals and all things pet care. My two dogs have brought me and my family immense joy and has gave me an appreciation for keeping pets safe and happy. I am currently working full-time on rover! I have plenty of availability to care and look after your pet. My weekdays are available where as my weekends are not, but please let me know if you have any weekend needs to be met. I have two kind poodles to keep your pet company! My home also has a secure fenced in yard, perfectly safe for your fur baby.

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Over 4
pet parents in Headingley have booked house sitting

Headingley pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

We had Eleni watch our dog (Jack) and cat (Morty) and she was absolutely wonderful! She was so kind and helpful, very communicative throughout the entire stay, and kept us well-informed with updates. Both pets were happy and well cared for when we returned, and it gave us real peace of mind knowing they were in such good hands. Eleni went above and beyond, and we’ll definitely be booking her again in the future. Highly recommend!

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Riley M.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Headingley is $50

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Headingley average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Headingley on Rover as of Mar 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

As of Mar 2026, there are 227 house sitters in Headingley. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 88% of Headingley house sitters respond in under an hour.

House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Headingley.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Headingley house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.