Dog Walkers in Headingley

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Top rated Headingley dog walkers

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

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Sitter Profile Image: Shayleece R.
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Shayleece R.
$17
total per walk
5.0 out of 5 stars
7 reviews
3 repeat clients
10 years of experience
Winnipeg, MB, R2Y

Shayleece has been here 11 days now and has built a relationship with Chewie. Chewie is excited to see her when she arrives which is a great sign. I’m thankful to Shayleece for walking the dog for me.

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Jeff & Christina P.
Sitter Profile Image: Kristin C.
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Kristin C.
Star Sitter
$28
total per walk
5.0 out of 5 stars
44 reviews
15 repeat clients
15 years of experience
Winnipeg, MB, R2Y

Kristin was great with Kingsley! She was very professional, and it was obvious during the meet and greet that she has a lot of experience with dogs!

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Nicole N.
Sitter Profile Image: Steve H.
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Steve H.
$23
total per walk
5.0 out of 5 stars
5 reviews
1 repeat client
40 years of experience
Winnipeg, MB, R2Y

i just started having steve walk my 2 puppies but so far all is wonderful. my puppies were really happy when i got home and were relaxed as they had a chance to blow off some steam when out for their walk with steve. i have steve doing ongoing walks with them and it really gives me peace of mind and he has shown he is very trustworthy. thank you steve.

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Lenore C.
Sitter Profile Image: Amelie P.
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Amelie P.
$22
total per walk
5.0 out of 5 stars
3 reviews
16 years of experience
Winnipeg, MB, R3K

About: Hi there ! My name is Aimee, I’m a 22 year old University of Manitoba student athlete and of course an animal lover. I grew up around cats and multiple dogs that provided me with crucial experience in caring for pets through feeding, bathing, training, walking, vet visits, and lots of love and affection. I would love the opportunity to care for and keep active with your pets throughout this summer, as well be a help to those with busier schedules! I’m currently a University student who has a lot of free time through the week. I just finished my summer classes and will be returning back to school at the beginning of September, leaving me with plenty of free time throughout the weeks for the rest of the summer! In my personal life at home we have a long gated back yard allowing for lots of room to run around. I care for my pets and others pets by playing with them outside or taking them for walks if a backyard is not available. I love to be active and bring along my pups on any adventures that is safe for them. I follow a routine feeding schedule and always have water available, except after extensive physical activity for about 15 minutes. I have no problem with the pets up on the couch to rest, but have beds for them to lounge on as well!

Sitter Profile Image: Kristy S.
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Kristy S.
$28
total per walk
35 years of experience
Winnipeg, MB, R3R

About: Hi :) I am someone who treats every pet like they're my own - not just cared for, but genuinely understood. I know how important it is to trust the person looking after your fur-babies, because they're family. I pay close attention to each animal's personality, routines and little quirks so they feel safe, relaxed and happy while you're away. Whether your dog needs long, energy burning walks or they prefer quiet company and gentle care, I adjust to them - not the other way around. What sets me apart is the level of attention and communications I provide. You'll always know how your pup is doing with regular updates, photos and honest check-ins. I'm reliable, patient and calm under pressure, which helps even anxious or shy dogs feel comfortable. I's also experienced with: 1. different energy levels (from playful pups to senior dogs.) 2. Administering basic medications if needed 3. Maintaining routines (feeding, walks, etc) 4. Giving lots of affection while still respecting boundaries At the end of the day, my goal is simple: your pet feels safe, loved and stress-free - and you have complete peace of mind. Pet care is my full-time focus, which means I've built my daily and weekly routine entirely around the needs of the pets I care for. I schedule my days to allow for consistent walks, check-ins, playtime and companionship, ensuring every pet gets reliable, unrushed attention. Your pet won't be "fit-in" - they'll be a priority in my day. When caring for pets in your home, I aim to keep everything as close to their normal routine as possible. I follow feeding schedules, walk routines, and household guidelines carefully so your pet feels secure and stress-free in their own environment. I treat your home with the same respect I would my own - clean, tidy and secure at all times. I'm mindful of details like locking up properly, keeping things organized, and maintaining a calm environment for your pet. You can also expect regular updates, photos, and honest communication so you always feel connected and at ease while you're away. I understand that inviting someone into your home requires trust, and I take that responsibility seriously.

Sitter Profile Image: Ahmed S.
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Ahmed S.
$15
total per walk
15 years of experience
Winnipeg, MB, R3J

About: I’ve been caring for pets since I was 15, which basically means I’ve spent years being bossed around by tiny fluffy supervisors. From energetic puppies to “I’ll sit if I feel like it” cats, I’ve done it all including walks, feeding, playtime, and of course expert level belly rubs. I take their care seriously, but I also bring plenty of fun, patience, and treats with permission of course. Your pet will be safe, happy, and probably a little spoiled! 😄 I currently work part time, which means I have a very flexible schedule and plenty of time to care for your pets. I’m happy to work around your routine and do my best to accommodate your preferred times for walks, visits, or stays. Whether you need something regular or last minute, I’ll always try to make it work! Your pet’s safety and comfort are always my top priority. During visits and drop ins, I stick closely to your pet’s routine including feeding, walks, playtime, and any special instructions so they feel comfortable and stress free. I’m respectful of your home and make sure everything is secure before I leave. I always keep a close eye on your pet’s behavior and well being, and I’ll send updates so you know they’re happy and in good hands.

Sitter Profile Image: Cara S.
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Cara S.
$23
total per walk
1 repeat client
15 years of experience
Winnipeg, MB, R3K

About: Ive loved animals my whole life and Ive had dogs in my life for around 15 years. I love to train, play, walk and love dogs and you can guarantee that your fur babies will be in the best hands possible. I am currently without a job so i am free to be able to entertain and love your fur babies while you are unable to! I have a fenced in yard that will keep all dogs safe. I have a 13 year old shitzu who spends her time on the couch, a 2 year old goldendoodle who is so friendly and sweet and would love to play and go for walks. He follows a schedule of training and walks that he would love a buddy to join him or he is happy to stay at home while i walk your dog!

Sitter Profile Image: Smruti S.
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Smruti S.
$18
total per walk
3 years of experience
Winnipeg, MB, R3N

About: I treat every pet like they’re my own, focusing on their unique needs and routines. My background in handling a wide range of animals ensures your furry friends are in capable, loving hands. Whether it’s a puppy with endless energy or a senior needing gentle care, I tailor my approach to make them feel comfortable and secure. Pet care is a natural and fulfilling part of my daily routine. I plan my schedule around providing top-notch care, ensuring pets get the attention they deserve. Whether it’s morning walks, afternoon playtime, or evening cuddles, I dedicate time to keeping pets happy and healthy. I’m flexible and organized, allowing me to adjust my week to accommodate different needs, from drop-in visits to extended stays. Caring for pets doesn’t just fit into my life—it’s a passion I prioritize every day. I provide personalized care that fits seamlessly into your pet’s routine, ensuring they feel comfortable and secure while you’re away. In every visit, I prioritize maintaining a clean and calm environment for your pet, ensuring they feel secure in their familiar space.

Sitter Profile Image: Ann N.
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Ann N.
$23
total per walk
15 years of experience
Winnipeg, MB, R3H

About: I’ve been a lifelong dog lover and have had the privilege of raising both rescue dogs and a purebred Golden Retriever over the years. Each one has shaped how I care for animals—with patience, understanding, and a lot of love. In our home, pets truly are family. Their happiness, comfort, and well-being are always a top priority, just as if they were children. I understand how important it is to trust someone with your dog, and I take that responsibility seriously. I’m known for being kind, conscientious, and reliable—not just with dogs, but with people too. I’ll always communicate clearly, show up when I say I will, and make sure you feel confident your pet is in good hands. I’m currently working part-time, which allows me to dedicate quality time and attention to the pets in my care. My approach is simple—I care for every pet as if they were my own. That means plenty of exercise tailored to your dog’s individual needs, along with a strong focus on mental stimulation through enrichment, play, and engagement—not just walks. In a client’s home, I respect your pet’s routine and environment, keeping things as consistent as possible to reduce stress. I make sure they receive plenty of attention, exercise, and mental stimulation, while also giving them the patience and calm presence they need to feel at ease. I care for every pet as if they were my own—prioritizing their comfort, happiness, and well-being at all times.

Sitter Profile Image: Whit R.
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Whit R.
$28
total per walk
5.0 out of 5 stars
70 reviews
27 repeat clients
11 years of experience
Cartier, MB, R4K

Whit was a saviour for us and Birdy. Her experience and love for dogs made us feel comfortable leaving Birdy in her hands. We will definitely be in contact in the future.

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Elise V.
Sitter Profile Image: Sarah M.
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Sarah M.
$25
total per walk
25 years of experience
Winnipeg, MB, R3M

About: Having grown up in a family with 3 cats and a dog, I've always had a strong love and interest in animals. I feel that I can really relate to the animal and get a sense of their soul. I looked after both dogs and cats while travelling in Europe. (During this time, I was working remotely as a freelance translator.) I have experience with various breeds, in particular, greyhounds, as I had an extended sit caring for a senior Spanish greyhound for 6 weeks. I have also cared for multiple cats and dogs at the same time, as I looked after 2 dogs and 2 cats at a house sit in England. I am based in Winnipeg and have a car to get to your location. I am a self-employed freelancer with plenty of spare time for pet care. At the moment, I am devoting most of my time to animal care. I always treat my clients' home and property with the upmost respect and I pay particular attention to the hand-over procedure and any special details or information about your home and/or your pets. I love animals and will look after your pets as if they were my own.

Sitter Profile Image: Julia B.
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Julia B.
$28
total per walk
5.0 out of 5 stars
6 reviews
1 repeat client
7 years of experience
Winnipeg, MB, R3J

About: My name is Julia and I have been dog and cat sitting for over 7 years and have owned multiple pets. I love animals, and have a chihuahua, papillon and husky! My husky is 2 years old and we’re always out for walks, playing at the park and training. I am always mindful of space, mood and boundaries when interacting with any animal I am caring for. I have been a pet sitter for the past 7 years because I love meeting new animals and genuinely enjoy being around & caring for them. I would love to meet you and your pet (even though they really are family)! I am available for pet sitting and drop in visits throughout the week and weekend. I have a flexible schedule and am able to accommodate I am always mindful of gates and fences / doors when letting animals outside. Making sure that doors and gates are closed as well as any escape holes covered. I am checking on the animals periodically throughout the day. I typically crate my large dog at bed time and let the two little ones sleep in bed with me.

Sitter Profile Image: Hadas K.
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Hadas K.
$34
total per walk
5.0 out of 5 stars
2 reviews
16 years of experience
Winnipeg, MB, R3N

About: Hello! My name is Hadas and I am a dedicated pet sitter and dog walker based in Winnipeg. I am 26 years old and work full time from home during the week so my schedule is flexible. I have a passion for caring for animals, and I specialize in providing services for both cats and dogs. I am a big animal lover. I currently have three cats (one senior) and have experience with puppies and senior dogs. 🐶🐈‍⬛ I currently work home full time Monday to Friday 8-4:30. I am always home during the weekends as well. I have a very flexible schedule and can be with your pet all the time and give it all of the love and attention they need and deserve. My home is a very clean, organized and safe place. I have three cats who love dogs. Two of them are four years old and the other one is 11. They are all in great health condition, are fixed and have all their vaccines. We recently had our senior dog pass away and they all got along great. As long as your dog is cat friendly there won’t be an issue.

Sitter Profile Image: Olivia C.
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Olivia C.
$50
total per walk
13 years of experience
Winnipeg, MB, R3N

About: I provide attentive, patient, and highly personalized care tailored to each pet’s individual needs and personality. I’m comfortable caring for energetic puppies, senior pets requiring gentler support, administering routines consistently, and creating a calm, trustworthy environment where animals feel safe, comfortable, and genuinely cared for. I am home for the summer from college and have very open availability to make your pets my priority. I can tailor my schedule to prioritize any needs your pet might have and only need to be out of the house for a maximum of 4 hours at a time, but that can be altered depending on specific needs. No matter where the care is taking place, I offer I offer attentive, reliable, and compassionate support tailored to each pet’s routine, comfort level, and individual needs. I prioritize maintaining a calm, safe, and familiar environment through consistent feeding, exercise, playtime, affection, and communication with owners to ensure pets feel secure and well cared for while away from their families.

Sitter Profile Image: Hayley S.
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Hayley S.
$23
total per walk
25 years of experience
Rosser, MB, R0H

About: Animals have been a huge part of my life from day one. I’ve spent 25 years caring for pets, from playful puppies and curious kittens to senior dogs and cats needing meds and extra TLC. I’ve had both large and small dog breeds, and I’m confident handling everything from daily walks to administering medications and sticking to routines. I’ve also cared for cats of all ages, including grooming, litter box upkeep, and giving oral meds. On top of that, I grew up around horses and even had two of my own, so I’m comfortable around animals big and small. I treat every pet like family and make sure they feel safe, loved, and happy while you’re away. My life truly revolves around animals, they’re a top priority in my daily routine. I'm used to planning my day around feeding schedules, playtime, walks, and medication when needed. Pet care isn’t something I squeeze in, it’s something I genuinely love and make space for. Whether it’s early mornings or evening check-ins, I’m flexible and committed to making sure your pets get the attention and care they deserve. At my home, pets have plenty of space to roam and play. I live on an acreage with an underground fence, so dogs get lots of safe outdoor time. I share my home with 3 friendly dogs and 4 cats, so your pet will be part of a loving, animal-friendly environment. We have kennels available for pets who are crate-trained or need their own space, as well as quiet areas for pets who prefer a calm, low-energy setting. I’m also happy to care for pets in their own home, offering visits, walks, litter box cleaning, playtime, and lots of love. I can easily adapt to whatever your pet needs to feel safe and comfortable.

Sitter Profile Image: Andrew H.
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Andrew H.
$18
total per walk
1 repeat client
2 years of experience
Winnipeg, MB, R3M

About: For any boarding and sitting needs a charming 3-story house is great for cats lots of rooms to hide. The yard is not good for dogs, is the only drawback. Located conveniently close to downtown, assiniboine park, Corydon Dog-walking would make the most sense the neighbourhood is perfect for it, I enjoy an active lifestyle. I am a qualified shelter assistant at the winnipeg humane society where we walk dogs, and I am trained in other areas of care as well I come from a safe, reliable family we are all friendly caring and trustworthy Available full-time for house sitting able to provide constant care and attention. I like to play guitar and sing your pets may like it Clean, spacious house lots of love

Sitter Profile Image: Khushi K.
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Khushi K.
$23
total per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
2 years of experience
Winnipeg, MB, R3C

About: I have 2 years of experience plus Im a dog trainer. i have one husky and a cat in my house They both are Friendly. There’s a off leash park just rights beside my appartment and Pickup drop off service available I love spending time with pets and After every 2 hours i take my Pets to park to get socialized in pack of dogs . I have special diet available if needed and Im pretty experienced with pets. Plus I love spending time with any kind of pet breeds rather big or small.

Sitter Profile Image: Daryna H.
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Daryna H.
$17
total per walk
10 years of experience
Winnipeg, MB, R3C

About: I grew up around animals and have years of hands-on experience with both dogs and cats. I’m patient, reliable, and understand how to care for pets of all ages — from playful puppies to gentle seniors. I offer loving, safe walks and drop-in visits with full attention to your pet’s needs. I usually take care of pet walks after 4 PM and am available for walks or visits then. My schedule is flexible in the afternoons and evenings to fit your pet’s needs. I prioritize creating a safe, calm, and loving environment for every pet, whether in my home or the client’s. I follow all care instructions carefully, keep hazardous items out of reach, and supervise pets closely during walks and playtime. Trust and open communication with pet owners are very important to me to ensure pets feel comfortable and well cared for at all times.

Sitter Profile Image: Charlotte P.
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Charlotte P.
$22
total per walk
10 years of experience
Saint François Xavier, MB, R4L

About: I’ve always had dogs in my life, from growing up with a Lab to now having a Chihuahua-Pom mix. I’ve been dog sitting and walking off and on since I was 15, helping out family, friends, and neighbors whenever they need an extra hand. I regularly dog sit for my boyfriend’s sisters and my grandma’s neighbor, so I’m used to all kinds of routines and personalities. Whether your dog is high-energy and loves adventure or prefers a more relaxed pace, I’m happy to match their vibe. I love keeping dogs engaged with walks, playtime, and activities that make their time with me fun and enriching! Pet care fits easily into my routine! I work Monday to Thursday evenings (3-11 PM), so I’m available for morning visits, walks, or check-ins on those days. On weekends, I’m completely free and can devote as much time as needed to make sure your pets are happy, comfortable, and well cared for. Whether it’s a quick visit, a long walk, or an overnight stay, I’m flexible and happy to work around your pet’s needs. I always prioritize safety, trust, and making sure pets feel comfortable in their environment. Whether I’m caring for pets in their home or out on a walk, I pay close attention to their needs, routines, and any special instructions from their owners. I make sure to keep a calm and positive atmosphere, giving pets space when they need it and attention when they want it. If a pet has any specific needs—like medication, meal schedules, or extra playtime—I’m careful to follow their routine to keep them happy and stress-free. My goal is always to make sure pets feel safe, cared for, and relaxed while their owners are away.

Sitter Profile Image: Sarah W.
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Sarah W.
$34
total per walk
5.0 out of 5 stars
2 reviews
2 years of experience
Winnipeg, MB, R2Y

About: I have experience with my puppy at home who is my pride and joy! He is a beagle mix, almost 3 years old and about 20 lbs. He is my first dog and a covid puppy so he definitely is the king of the household! I have experience pet sitting in the past,I love meeting, getting to know and growing connections with all animals I get to pet sit for! I currently am working full time with consistent hours and breaks, I can provide bathroom breaks to the animals on my break as well as spending lots of time with them on the evenings/weekends I go on multiple walks a day with my dog, I have a very friendly dog that would keep your dog company! I can crate any dog if needed

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The median cost per walk for dog walking in Headingley is $20

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Sitters in Headingley average 4
repeat dog walking clients

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Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Headingley on Rover as of Jun 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

As of Jun 2026, there are 336 dog walkers in Headingley. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 84% of Headingley dog walkers respond in under an hour.

Dog walkers in Headingley have an average of 14 years of experience. Dog walkers with repeat customers have an average of 4 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Headingley.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 336 dog walkers in Headingley on Rover, so you’re sure to find the perfect match for your dog! In Headingley, 86% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

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