House Sitting Headingley

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Over 28
pet parents in Headingley have booked house sitting

Headingley, Find top rated house sitting

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: Rp S.
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Rp S.
Star Sitter
$60
total per night
5.0 out of 5 stars
• 107 reviews
33 repeat clients
24 years of experience
Winnipeg, MB, R2L

“Rp was excellent. The planning around my weekend away was extremely easy because they’re very communicative and responsive. They even planned for the potential that I was delayed on my return, making themselves available past the agreed on departure time in case it was needed. They provided daily updates with what the dogs got up to and how the days/nights were structured, and sent photos regularly.”

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Beverly P.
Sitter Profile Image: Kristin C.
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Kristin C.
Star Sitter
$50
total per night
5.0 out of 5 stars
• 61 reviews
23 repeat clients
15 years of experience
Winnipeg, MB, R3J

“Kristin took care of our dogs amazingly! Chico and Juno warmed up to her very quickly, and we were sent many photos of the dogs throughout our vacation. She also cleaned our house before our return, such as the bed sheets and blankets in the room she was staying in, and Juno’s diapers. She’s an all-around amazing pet-sitter!! Thank you so much Kristen!”

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sandra c.
Sitter Profile Image: Kirsten M.
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Kirsten M.
$45
total per night
5.0 out of 5 stars
• 5 reviews
23 years of experience
Headingley, MB, R4J

“Kirsten went above and beyond. Our dog was walked routinely and cats had play time. Our recycle and garbage were emptied and floors were swept. Far exceed our expectations. Clear and consistent communication. Kirsten is a lovely articulate young lady; our animals were in good spirits upon our return”

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Katherine R.
Sitter Profile Image: Brena D.
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Brena D.
Star Sitter
$67
total per night
5.0 out of 5 stars
• 133 reviews
45 repeat clients
20 years of experience
Winnipeg, MB, R3L

“Brena was wonderful! We received lots of pictures of our bullies. They looked quite happy to cuddle with her. I’m sure they are looking forward to seeing Brena next month!”

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Lucille R.
Sitter Profile Image: Natacha T.
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Natacha T.
$73
total per night
5.0 out of 5 stars
• 62 reviews
17 repeat clients
20 years of experience
Winnipeg, MB, R3J

“Natacha was an absolute delight! So kind, friendly, respectful, and accommodating. Our very anxious bulldog loved her and she was knowledgeable about how to navigate our dog’s separation anxiety. We look forward to having her care for our pets again!”

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

“Shayleece was amazing with my dog, Osito. He took to her right away. She was responsible with his health and food. I had to extend my trip for business reasons and she was very flexible. I couldn't have asked for better care. She also took good care of my house. Osito was well cared for and very comfortable with her. Excellent care. Thank you so much for the help.”

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Aaron S.
Sitter Profile Image: Hayley B.
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Hayley B.
Star Sitter
$67
total per night
5.0 out of 5 stars
• 4 reviews
5 repeat clients
10 years of experience
Winnipeg, MB, R2M

About: I currently work at a doggy daycare and am in school to become a veterinary assistant, so I have experience caring for all different kinds of dogs and animals! I have 2 dogs of my own, one is a puppy I’m raising, and they are just the sweetest things. I work 1 day a week, so other than that all of my time is free and flexible to work around your schedule and your needs! I promise to take as good of care of your fur babies as I do of my own! I care for them in the comfort of your own home! So they don’t need to get used to a whole different environment. I do daily drop-ins, dog walks, and overnight pet sitting.

Sitter Profile Image: Ann N.
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Ann N.
$67
total per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
15 years of experience
Winnipeg, MB, R2H

“Ann was amazing. Our springer spaniel, who doesn't like almost ANYBODY at first, took to her immediately. Ann demonstrated over and over that she cared for our dog as if he were her own, and sent consistent updates which were very appreciated. Would absolutely book with her again.”

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Chris A.
Sitter Profile Image: Princess O.
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Princess O.
$73
total per night
5.0 out of 5 stars
• 30 reviews
10 repeat clients
6 years of experience
Winnipeg, MB, R3C

“Princess did a great job with Abby and Rosie! The pups seemed to enjoy her very much. She seems confident and very comfortable with dogs and we’re very pleased with her service. We would definitely book her again!”

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Cheryl C.
Sitter Profile Image: McKenna W.
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McKenna W.
$50
total per night
14 years of experience
Winnipeg, MB, R3R

About: I grew up in households with pets my whole life including both dogs and cats! With my own fur baby now that is 13 years old I am well equipped to take care of older pets. I love spending time with pets of all sizes and ages and would love to get to meet your pet! I am currently a student so when I am not attending a class I have full availability to provide care to your pets. I am fully available to spend time with your animals on weekends and in the mornings, evenings and nights during the week! I would love to meet with your pets ahead of time to learn their routines and comfort levels to ensure I can provide the most comfortable and safe care possible for your pet! With multiple years of experience with pets of different sizes I am fully comfortable with dog walking, crating animals when requested and accommodating special needs.

Sitter Profile Image: Avery B.
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Avery B.
$56
total per night
5.0 out of 5 stars
• 27 reviews
8 repeat clients
17 years of experience
Winnipeg, MB, R3V

“Avery did a great job caring for our 5 senior animals with special needs. She also house sat for us and did an excellent job taking care of our house during a Winnipeg winter. She is our go to when we are on holiday or away from the house for an extended period of time.”

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Dan F.
Sitter Profile Image: Amanda B.
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Amanda B.
$67
total per night
5.0 out of 5 stars
• 3 reviews
24 years of experience
Winnipeg, MB, R3J

“Amanda was very attentive to my dogs . She took amazing care of them. She also walked them and sent pictures. I would definitely recommend Amanda for your puppy care”

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Rosemary M.
Sitter Profile Image: Ulyana K.
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Ulyana K.
$89
total per night
5.0 out of 5 stars
• 19 reviews
3 repeat clients
8 years of experience
Springstein, MB, R0G

“This was my first time using this service and I was a little nervous, but as soon as I met Ulyana I felt at ease. While I was away she kept me updated as well as sent me photos of Cali, which was fantastic. She took good care of Cali and left my home spotless. I highly recommend Ulyana and I will definitely rebook her again if I need. She is an absolute pleasure and she took such great care of my Cali.”

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Shannon H.
Sitter Profile Image: Jonathan D.
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Jonathan D.
$45
total per night
5.0 out of 5 stars
• 3 reviews
2 repeat clients
2 years of experience
Winnipeg, MB, R3C

About: Your pets deserve more than just someone to feed them and let them outside, they deserve someone who genuinely enjoys spending time with them. Whether your pet loves long walks, playtime, cuddles on the couch, or simply having a calm and caring companion nearby, I'll make sure they feel safe, comfortable, and loved while you're away. I understand that every pet has a unique personality and routine, and I take the time to learn what makes your pet happiest. I have experience walking dogs at the Humane Society for around two years and I grew up with a dog for 18 years. My goal is simple: to treat your pets with the same care, patience, and attention I'd want for my own. My schedule is very flexible, which allows me to provide reliable and consistent care throughout the week. I'm available for morning, afternoon, evening, and weekend visits, and I can often accommodate last-minute bookings when needed. I understand that pets thrive on routine, so I make every effort to work around their normal schedule for feeding, walks, playtime, medication, and bedtime. Whether you need regular care while you're at work or someone to look after your pet while you're away, I'm committed to providing dependable care and keeping you updated every step of the way. The safety, comfort, and well-being of every pet in my care is my top priority. I take the time to learn each pet's routine, personality, and any special instructions so they can feel as comfortable as possible while you're away. I provide a calm, supervised environment and always pay close attention during walks, playtime, feeding, and outdoor activities. I follow all owner instructions carefully, including medication schedules, dietary needs, and behavioral preferences. I also believe that communication is an important part of pet care. You'll receive regular updates and photos so you can feel confident that your pet is safe, happy, and receiving the attention they deserve. My goal is to create a positive, stress-free experience for both pets and their owners.

Sitter Profile Image: Kamil M.
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Kamil M.
$45
total per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
20 years of experience
Winnipeg, MB, R2J

“Kamil was great with my 90 kilos English Mastiff, Bane. He tried to get along with him, good during the walks, and the time spent during the day care.”

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Ellie L.
Sitter Profile Image: Cindy H.
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Cindy H.
$78
total per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
20 years of experience
Winnipeg, MB, R3T

“This was the second time Cindy stayed with my crew and she's so great with them! I have a reactive dog and 3 cats (2 of them on the shy side) and not only does she handle each of their individual personalities and needs like a pro, she genuienly enjoys the weird little things that make them who they are. It's a HUGE relief to find a sitter who's equally capable with all 4 of them *and* who understands and has limitless patience for my anxiety about leaving them. If I could leave more stars I would!”

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Jill S.
Sitter Profile Image: Aalisha P.
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Aalisha P.
$45
total per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
Winnipeg, MB, R2M

About: I grew up with birds and cats! My kitty is a year younger than me. I have 10+ years in experience with pet and babysitting x My availability is quite flexible! I prefer working in the afternoon or evening. However I don’t mind mornings! I am usually free on weekends x I have a 21 year old cat! She cannot eat dry food. Due to her age she most likely has dementia.. in order to make it easier for her we have two litterboxes x

Sitter Profile Image: Ryan H.
Verified Background Check
Ryan H.
$45
total per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
6 years of experience
Winnipeg, MB, R3G

About: I've cared for a bunch of dogs through dog-sitting and have lived with, cared for, and become close to several dogs and cats. I've also done a lot of research regarding cats & dogs - but I'm very respectful of owners’ beliefs and instructions. I have a pretty flexible schedule right now because I'm self-employed with another business as well. I'm generally available 7 days a week, depending on my other work and plans. I can care for pets in my home or at your home. My home is clean, safe and has room for pets to play and relax. I have lots of toys for dogs and cats, and depending on the pet, we can also spend time in the yard or go for walks.

Sitter Profile Image: Angela S.
Verified Background Check
Angela S.
$50
total per night
30 years of experience
Winnipeg, MB, R3G

About: I've been a cat owner for most of my adult life and have also done cat sitting, dog walking/sitting for friends and family over the years. Starting at the end of August I'll be working part-time (4 days per week) and can do early morning visits/walks or late afternoon early evenings. I treat all my own and other's pets with lots of love. I generally prefer animals to people and most people would say I'm a natural with animals.

Sitter Profile Image: Jacey H.
Verified Background Check
Jacey H.
$45
total per night
15 years of experience
Winnipeg, MB, R3K

About: I have been caring for pets throughout my life and have gained hands-on experience working at a dog daycare, as well as providing in-home pet sitting for dogs and puppies. I am passionate about ensuring every pet feels safe, comfortable, and well cared for while their owners are away. I currently work Monday-Friday. My hours are 8:00-4:30. I have time to care for your pet in the mornings, evenings, weekends and on my lunch break. I would assure your dogs have a safe space inside and outside and are cared for to the best of my ability. I treat every pet like they are my own.

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

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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

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  • Reservation protection

    It doesn’t happen often, but if your 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.

How to book house sitting

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for house sitting - Headingley

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Sitters in Headingley average 4
repeat house sitting clients

FAQs for House Sitting - Headingley

Frequently asked questions about Rover

The average cost of House Sitting in Headingley on Rover is $44 per night as of October 2026. Most bookings cost between $35 and $56 per night. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 246 sitters on Rover offering House Sitting across the city of Headingley. About 91% typically respond to requests within 60 minutes.

Enter your address and booking dates to see which sitters are available near you. You can also message multiple sitters to improve your chances of finding the right care.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Headingley maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

<b>Tip:</b> Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Garbage & recycling: Taking garbage bins to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Headingley walking routes, the location of your favourite pet store, and any specific quirks about your home’s security or appliances.

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!

You can find what you need to review a sitter on their profile before booking with them. Each sitters’s profile on Rover shows verified reviews, a background check, and ratings to give a glimpse of how their previous visits went. You can also use the Meet & Greet to walk through your home, identifying which areas, like your bedroom, are off-limits or not. Requesting details of your home security through the app can also be a good way to have your sitter keep you updated about your home.

If you have security cameras or doorbells, Rover asks that you disclose them to sitters before you book.

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 .

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 , which provides up to 25,000 in eligible veterinary care reimbursement.

Payment is handled securely through Rover. For a one-time booking, at the time of checkout when you submit your booking request. This charge will include fees payable to Rover. Your booking is confirmed once the sitter accepts it.

If the request is not accepted, the pending charge is released in 1-7 days. How long it takes to disappear from your account depends on your payment provider.

For eligible recurring weekly services, you are charged for the first week when you book and then each Monday for the upcoming week. You’ll see the full price before you confirm. Always pay through Rover so your booking remains eligible for the Rover Guarantee and support.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our .

Yes, you can find sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and request a Meet & Greet to walk your sitter through your expectations.

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