Dog Sitting in Headingley

Book a Headingley dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Headingley dog sitters

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

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Sitter Profile Image: Olivia C.
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Olivia C.
$34
total per visit
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: Hanna B.
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Hanna B.
$28
total per visit
15 years of experience
Winnipeg, MB, R3C

About: I’ve taken care of dogs since I was young, it’s fulfilling and gives you another reason to be happy! This is an exciting experience to be around other dogs and take care of the animals you all love so much! I have a very flexible schedule, I work at a hockey camp a couple times a week. I love going for long walks or sometimes runs and I've been to the dog park on numerous occasions with my friends and their pups, and my own as well! In home i’ll ask the basic questions to see what your daily schedule looks like and I will adjust to that for however long i’m with your dog! I can also come for a meeting before I look after your furry friend just to get accommodated!

Sitter Profile Image: Ahmed S.
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Ahmed S.
$15
total per visit
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: Jansher S.
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Jansher S.
$34
total per visit
1 year of experience
Winnipeg, MB, R3K

About: I have a experience of nearly a year I have a dog back at my home in India. I just love him so much I used to take to walks in the park, play with him over there. Overall I kinda of like animals and I love to play with them whether it's a dog or a cat etc. I just love to play with animals and I like to care them. I am sure that your pet will have a wonderful time with me. I am available to take care of your pets every evening and all days on weekends. I am available on all holidays to take care your pet. I live in a quite and pet friendly neighborhood with ample space for your pets to enjoy. With open roads nearby and parks to enjoy.

Sitter Profile Image: Arielle K.
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Arielle K.
$28
total per visit
4.9 out of 5 stars
46 reviews
14 repeat clients
6 years of experience
Winnipeg, MB, R2V

About: NOTE: meet and greets required prior to booking, no day of boarding. Hi all! I have a large back yard with tons of room to run & play. I also have two dogs who love to socialize and play. My full time job requires me to be away from the house for a few hours a day but my boyfriend is home by 3pm daily (who is also rover certified) so they’re never left alone long! I have a lot of experience watching dogs, I’ve watched for friends and family of a variety of sizes and breeds. I’m experienced with giving oral medications and insulin. I also have 10 months of experience working at a dog daycare. My dogs are open to playing with dogs of any age or size even small dogs! We’re very dog friendly at our house our dogs are spoiled and have range to lay on the couches with us, look out the window from our bed and have tons of pillows laying around as well! We have tons of treats, toys, a big refillable water bowl & even a pool for the summer time heat! Come give us a visit and leave feeling at ease while you’re away!

Sitter Profile Image: Denae E.
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Denae E.
$25
total per visit
5.0 out of 5 stars
16 reviews
3 repeat clients
9 years of experience
Winnipeg, MB, R2J

About: I have only recently begun expanding who's animals I take care of but have been taking care of my personal pets all my life. I have experience with cats, dogs, small mammals and amphibians. I have cared for all ages of pets including newborns and geriatric. I can handle administering medications of different sorts. I have first aid training, human and animal. If you have a specific way of doing things that you'd like continued I am more then happy to do so. My main concern is that your family member is well taken care of whether it be for an hour, a day or several days at a time. I have a schedule that is constantly changing. I am doing a training program come early 2025 so my schedule will be tighter than it is now but I will still try to arrange you to fit in. Keeping your pet safe is a big concern. I always check collars and leashes prior to use to ensure their functionality. I do have a dog who loves playing with others if yours needs a companion.

Sitter Profile Image: Roman S.
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Roman S.
$23
total per visit
5.0 out of 5 stars
10 reviews
2 repeat clients
20 years of experience
Winnipeg, MB, R2W

Roman has been checking in on my pup for the past couple weeks now and he’s been great. He treats my pup like his own which is awesome to see. Im afraid Duke likes him more than me! Highly recommend!

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Tanner J.
Sitter Profile Image: Cindy H.
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Cindy H.
$34
total per visit
20 years of experience
Winnipeg, MB, R3T

About: My husband and I have owned dogs for the past 15 plus years together, and our families both owned them for many years growing up. While he would not attend your home with me, I like everyone to know that our entire house is Pet lovers. My soft spot is for seniors, and dogs with varying degrees of health related issues. The ones that nobody wants and the often misunderstood ones. I have cared for a variety of breeds with varrying degrees of health issues. I have extensive experience in administering medications, IV fluids, intramuscular injections, eye drops, nail trims, and more. I have had 2 blind dogs (one of which had both of her eyes removed due to glaucoma), so am very familiar with their sometimes unique challenges. I also have experience caring for dogs with little to no hearing, as well as ones with various levels of behavioral challenges, such as resource/food guarding, stranger/leash aggression, and more. While I love a good puppy cuddle, my heart belongs to the older four (or less!) legged friends, and I would love the opportunity to meet your furry family members. I have an extremely flexible work from home/anywhere schedule with my current job, which allows me the freedom to help provide care for your furry family members. I can work from almost anywhere that has a charging outlet and a wifi connection, which i believe makes me an excellent choice for in your home care, or even a quick wellness visit! I love the idea of coming to your home to care for your pets, as it allows them to continue to feel safe and in a familiar environment. Following their regular routine helps make any time away from mom and dad as stress free as possible. Pets are never left outside unattended, and if you don't have a completely fenced yard, they will always be on a secure leash for potty breaks. If spending overnights in your home, I welcome the pets to share a sleeping space, or crate them as requested. Even if I do things different with my own pets, I want to ensure all of your rules and routines are followed while you are away.

Sitter Profile Image: Elise S.
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Elise S.
$24
total per visit
10 years of experience
Winnipeg, MB, R3N

About: I have spent the last 10 years walking and taking care of dogs of multiple ages. I am a university student who is looking for some odd jobs this summer, and thought since I love animals so much, I’d give this a try! We just lost our 16 y/o black lab/border collie mix in late June 2025 and I have gained so much extra patience and love for our old babies. I am open to walks, drop ins and staying with your pet while you’re away. I can provide references if needed! I look forward to meeting you and your pets During the summer time my availability will almost be entirely free. While you’re at work during the week, I’d be happy to come let your dog out or take them on a walk! If you’re planning a vacation I’d be happy to stay with your pet while you’re away Feeding, grooming, cleaning, walks or administering medicine. Spending time with pet playing or finding creative puzzles and treats to keep dog occupied and satisfied. Open to trying new things you do to take care of your pets!

Sitter Profile Image: Khushi K.
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Khushi K.
$28
total per visit
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: julianne p.
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julianne p.
$24
total per visit
6 years of experience
Winnipeg, MB, R3M

About: I truly love getting to know each dog's unique personality and making sure they feel safe, happy, and loved in my care. I have experience with dogs of all ages, including seniors who need medication or extra support. I also enjoy working with puppies, using patience and positive reinforcement to help them learn good habits and build confidence. My goal is always to care for every pet as if they were my own. ❤️ I currently work full-time but have a long enough lunch break to check in on pets as needed. My weekends are completely free, allowing me to provide dedicated care and attention. Additionally, I have many holidays available for full-time stays, and I’m especially flexible during the summer as i have the full summer off. This schedule lets me ensure your pets receive the care and companionship they need, while also allowing for regular updates and quality interaction throughout the day. I focus on creating a positive and engaging atmosphere, offering playtime, affection, and mental stimulation to keep them happy. Communication is key, so I provide regular updates and photos to keep you informed while you’re away!! Your pet’s happiness and well-being are my top priorities! I also am happy to attend to other needs of the home upon request, watering plants ect

Sitter Profile Image: Daryna H.
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Daryna H.
$24
total per visit
10 years of experience
Winnipeg, MB, R2H

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: Sarah W.
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Sarah W.
$28
total per visit
5.0 out of 5 stars
2 reviews
2 years of experience
Winnipeg, MB, R2Y

Sarah and Devon were fantastic. Very professional and easy to trust with both my cat and my house. They did everything I asked and sent plenty of pictures! I would absolutely recommend them to anyone.

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Justin D.
Sitter Profile Image: Omar R.
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Omar R.
$45
total per visit
5.0 out of 5 stars
6 reviews
11 years of experience
La Salle, MB, R0G

About: What sets me apart is my 11 years of hands-on experience raising my own dog from puppyhood to its senior years. I understand the patience needed for puppy training and the gentle, attentive care required for senior pets. I treat every guest with the same lifelong commitment and love I gave my own. Since I work from home, pet care is naturally integrated into my day. I provide constant supervision and companionship, taking regular breaks for walks, backyard playtime, and belly rubs. Your pet will never be alone and will enjoy a consistent routine right alongside me. I provide a secure, supervised, and loving environment. I specialize in maintaining consistent routines and constant monitoring to ensure every pet feels safe. From senior-friendly spaces to active puppy supervision, I use my 11 years of experience to manage potential risks and provide total peace of mind for every owner.

Sitter Profile Image: Storey Alexander W.
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Storey Alexander W.
$24
total per visit
5.0 out of 5 stars
3 reviews
1 year of experience
Winnipeg, MB, R3M

About: I have had dogs my whole life from puppies to senior dogs. I love spending time with the furry friends, and making sure that they have someone there when needed. I work Monday-Friday until 5pm in downtown Winnipeg so I am relatively close to every area of the city, I’m free all weekends, long weekends. I make sure that I’m attentive to how they behave , I ask what is normal for your furry friends so that if they are not behaving as expected then I can notify you immediately.

Sitter Profile Image: Fateme A.
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Fateme A.
$34
total per visit
5.0 out of 5 stars
2 reviews
1 repeat client
20 years of experience
Winnipeg, MB, R3Y

About: My childhood and youth were filled with a deep love for animals—especially cats and dogs. No matter if they were strays, I always made sure to feed them, play with them, and give them as much kindness as I could, just to see them happy. Over the years, I’ve had the joy of fostering several cats and even big dogs, and through those experiences, I’ve learned how to truly connect with them and understand their needs I currently working full time as an accountant, after 4:00pm I pretty free to take care of your pet till 8:00 pm , I am totally available on weekends I have a pet friendly apartment with a beautiful trail nearby to take your pets for walking, the apartment is two bedroom which I organized one bedroom specifically for pets

Sitter Profile Image: Carol N.
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Carol N.
$23
total per visit
5.0 out of 5 stars
3 reviews
10 years of experience
Winnipeg, MB, R3P

About: I have worked a lot with puppies. In obedience training using positive reinforcement only! I can handle big and small dogs and will make sure my pup gets along with yours before walking them together. However she gets along with most dogs. I spend most of my days making sure my girl has lots of exercise. She LOVES other dogs and is a very submissive playful girl. This is the main reason for my downloading this app. My dog needs friends. Haha! My pup will keep your pup company and there will be lots of trail walks if it’s suits your pup. Whatever your pups needs really. I’m a firm believer in allowing dogs to have “their time” if they want to sniff, they can sniff, or if they want to play or swim. This is their time to find their happy place. Of course with supervision.

Sitter Profile Image: Andrew H.
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Andrew H.
$23
total per visit
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: Shawn B.
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Shawn B.
$24
total per visit
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.

Sitter Profile Image: Hoi Chuen Richard L.
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Hoi Chuen Richard L.
$34
total per visit
5.0 out of 5 stars
3 reviews
15 years of experience
Winnipeg, MB, R3Y

About: Hello, pet parents! I'm Ric, an experienced dog daycare attendant and dedicated dog walker with a deep love for all things canine. With years of experience in the field, I have the skills and knowledge to handle dogs of all sizes and temperaments. Whether your pup needs a fun day at daycare or a refreshing walk, I ensure they receive the best care and attention they deserve. Trust me to keep your furry friends happy, healthy, and well-exercised! Pet care fits seamlessly into my daily and weekly routine thanks to my flexible schedule. I offer services on weekdays after 5 PM, perfect for those busy with work during the day. Additionally, I am available on weekends, including Sundays, to ensure your pets receive the care they need even during your off days. This flexibility allows me to provide consistent and dedicated attention to each pet, ensuring their health and happiness no matter the time of week. Caring for pets in my home or my client's home is a rewarding experience that I approach with dedication and love. For dog walking, I tailor each walk to fit the individual needs of the dog, ensuring they get the right amount of exercise and stimulation. Nail trimming is done with gentle precision, making sure the experience is stress-free for your pet. Brushing sessions are thorough, helping to keep your pet’s coat healthy and shiny while also providing a soothing, bonding experience. Whether at my home or yours, I strive to create a safe, comfortable, and enjoyable environment for your furry friends.

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The median cost per night for dog sitting in Headingley is $25

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Sitters in Headingley average 5
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Frequently asked questions about Rover

Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Headingley on Rover as of Jun 2026 was about $25 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

As of Jun 2026, there are 364 dog sitters in Headingley. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 87% of Headingley dog sitters respond in under an hour.

Dog sitters in Headingley have an average of 13 years of experience. Dog sitters with repeat customers have an average of 5 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Headingley.

Rover makes it easy to find Headingley dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

There are 364 dog sitters in Headingley on Rover, so you’re sure to find the perfect match for your dog! In Headingley, 100% of dog sitters offer daily exercise, 94% offer medication administration, and 88% 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 sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter 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.