Dog Sitting Headingley

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

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pet parents in Headingley have booked dog sitting

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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: 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: Sara v.
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Sara v.
$28
total per visit
5.0 out of 5 stars
1 review
2 repeat clients
6 years of experience
East Saint Paul, MB, R2E

About: I’ve been pet sitting for just over 6 years and have fallen in love with the work. I specialize in multi pet homes and furry friends that may have specialized diets and/or medication needs. I recently have relocated to the city after graduating school for aviation! I’m on a job hunt currently but for the time being my schedule is clear and open for your little one! Your pets safety and comfort is my top priority! My goals are to try and disrupt routines the least when you’re away from your pet as well as send regular updates and photos!

Sitter Profile Image: Hadas K.
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Hadas K.
$39
total per visit
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: 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: 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: 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: 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: 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: 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. As the owner of Manitoba's ONLY small animal rescue charity, I also have a wealth of knowledge and experience with exotic and small animals such as rabbits, guinea pigs, hamsters, 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: 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: 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: Julia B.
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Julia B.
$28
total per visit
5.0 out of 5 stars
6 reviews
1 repeat client
7 years of experience
Winnipeg, MB, R3C

Julia did such a good job looking after our Kitty!

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Pamela L.
Sitter Profile Image: Anshul P.
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Anshul P.
$24
total per visit
10 years of experience
Winnipeg, MB, R3B

About: I've taken care of dogs of every kind since I was 10. Neighbors, friends, and family have consistently relied on me to walk, feed, bathe, and provide compassionate care for their beloved pets. I have a deep love for animals and prioritize their well-being and happiness. I'm currently working part-time, so I'll have plenty of dedicated time to play with your pups! My flexible schedule allows me to offer boarding services on weekends, ensuring constant supervision. On weekdays, I am reliably available after 2 PM for walks, drop-in visits, or even extended playdates, making sure your pet receives consistent care and attention throughout the week. Your pet's safety is my top priority. My home boasts a securely fenced yard where pets can play freely and safely under constant supervision. I also have two very friendly and well-socialized dogs who love company and can provide a playful environment for your fur baby. Furthermore, I am fully equipped to responsibly crate your dog if needed for their comfort or safety, ensuring peace of mind for you. I am committed to maintaining a clean and secure environment

Sitter Profile Image: Yash K.
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Yash K.
$24
total per visit
1 repeat client
4 years of experience
Winnipeg, MB, R3Y

About: I have owned 2 dogs at the same time back home. Being home by self and work schedule makes it hard for me to own one right now. But to keep my affection towards dogs - I do walk dogs in the neighborhood whenever needed. I am a full time railroader, so I do have some time off between shifts that I can work towards becoming a sitter for dogs I can assure that your pet will be in safe hands while they are with me in my house and will get regular walks and good environment to stay at.

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: 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: 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.

Sitter Profile Image: Hayley S.
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Hayley S.
$20
total per visit
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: Meghan P.
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Meghan P.
$22
total per visit
5.0 out of 5 stars
2 reviews
1 repeat client
8 years of experience
Winnipeg, MB, R3G

About: I have fostered dogs from northern communities with various behavioural issues - from resource guarding to marking their territory indoors. Now I’m a foster fail with my own northern mutt! I offer a calm, clean, and friendly home for dogs of all sizes. I am currently working full-time on an office/home hybrid schedule. I have the availability to make my own schedule and choose when I work from home. Arrangements can be made should you require consistent supervisor of your pooch, however advance notice is required. I have a friendly and submissive five year old neutered male Shepard/husky mix who would love to play with your dog in our fully fenced in yard! We also typically go for two walks a day around our neighbourhood. When we aren’t outside, my dog and cat enjoy free rein in the house, including on furniture. My cat can be separated from your pet should it be required, with my cat getting the basement and your pet getting to stay upstairs with me.

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

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Sitters in Headingley average 5
repeat dog sitting clients

FAQs for Drop-In Visits - Headingley

Frequently asked questions about Rover

The average cost for Dog Sitting in Headingley on Rover is $27.75 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

There are 334 sitters on Rover for Dog Sitting in Headingley. About 86% of Headingley sitters can respond to requests in under 60 minutes. Whether you’re planning ahead for holidays, need last-minute care, or need same-day coverage for an urgent trip, you can message multiple sitters at once to find available care.

Once you find the right match, you can arrange a Meet & Greet to ensure they are a perfect fit for your pet’s personality before confirming.

Rover makes it easy to find sitters who are available during your working hours. To find sitters who fit your schedule, select which days of the week and the time slots you'd like a sitter to visit. The search results will populate sitters whose calendars match your needs. You can also search for sitters by location, whether that’s a sitter near your office for day care drop-off or a sitter close to your home. Once you've found a sitter who you like, message them directly to schedule a Meet & Greet.

Tip: Doggy day care is another option for pet supervision while you're at work. Visit our doggy day care page for more information.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or travelling for a few nights, a pet sitter can offer poop breaks during a Headingley stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover based on what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Headingley choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they do not have any disqualifying offences.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

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