House Sitting Headingley

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

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Over 31
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%.

1 / 1
Sitter Profile Image: Kristin C.
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Kristin C.
Star Sitter
$50
total per night
5.0 out of 5 stars
55 reviews
17 repeat clients
15 years of experience
Winnipeg, MB, R3J

kristin was very responsive and my dog was very happy when I got home so I know she had a good time with her. She seemed very relaxed and she also left me a lovely card and she sent me pictures while I was away and I would definitely use her again. Highly recommended!! oh and on another note, my dog who is normally pretty shy of people took about maybe 10 minutes before she got up off the floor and went over and greeted kristin and started giving her some kisses. Makes me very happy!!

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

Kirsten did a wonderful job of looking after our super cuddly girl and our home. She sent photos of their walks and cuddles and was always responsive to our messages. Would be happy to have Kirsten again as an overnight sitter!

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Lynda B.
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

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

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Aaron S.
Sitter Profile Image: Rp S.
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Rp S.
Star Sitter
$60
total per night
5.0 out of 5 stars
104 reviews
32 repeat clients
24 years of experience
Winnipeg, MB, R2L

This was our first time leaving our home and 2 Golden Retrievers in the hands of anyone outside of family, so understandably we were a little apprehensive. After our “Meet and Greet” with Rp, our minds were quickly put at ease. He was very personable, respectful, calm and clearly experienced, answering our questions and anticipating questions we didn’t even know we had. Both dogs took to him immediately! While we were away, Rp communicated with us daily, sending pictures and videos. Upon our return, our boys had obviously been very well looked after, the house was as we left it, and Rp was there to fill us in on the week’s events. We were extremely impressed and with total peace of mind, we will definitely rebook Rp again in the future. Thank you so much Rp! ?

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Debbie B.
Sitter Profile Image: Brena D.
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Brena D.
Star Sitter
$67
total per night
5.0 out of 5 stars
130 reviews
44 repeat clients
20 years of experience
Winnipeg, MB, R3L

First time using Rover. I returned home and my boys were not stressed or out of sorts, which tells me they were happy. My home was left tidy and the backyard was clean. My 2 dogs love their walks. I have a reactive pooch around other dogs and Brena happily walked him.

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michelle f.
Sitter Profile Image: Amanda B.
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Amanda B.
$67
total per night
5.0 out of 5 stars
2 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: Princess O.
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Princess O.
$78
total per night
5.0 out of 5 stars
28 reviews
9 repeat clients
6 years of experience
Winnipeg, MB, R3C

This is our second time booking Princess for house sitting; this time for a longer stay with both our dog and cat. Our pets love her and immediately feel at ease around her. Princess is incredibly respectful and tidy. I will be booking her again in the future!

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Melissa D.
Sitter Profile Image: Ranchelle O.
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Ranchelle O.
Star Sitter
$45
total per night
4.9 out of 5 stars
72 reviews
27 repeat clients
29 years of experience
Winnipeg, MB, R2R

We appreciated the meet and greet with Ranchelle as our dog is new to our family. We wanted him to feel comfortable with a new caregiver. We received many photo updates throughout the weekend. Ranchelle followed through with difficult walks as our dog is quite reactive.

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Jennifer 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
1 repeat client
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: Jacey H.
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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.

Sitter Profile Image: Lisa R.
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Lisa R.
$100
total per night
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Winnipeg, MB, R2Y

About: I absolutely love caring for all animals. Reptiles, dogs, cats, birds, etc! I worked at a pet store for awhile and also frequently babysat my friends two dogs. I have also taken care of my own cat for 10 years now, as well as my friends cat. I am aware of the difference temperaments dependent on breed, and dietary restrictions that they may have. I have always had a deep caring for animals and I would love to display that for your pets. Please note I am only accepting sitting bookings for the St James/Crestview/Charleswood/Polo Park area. Anything further unfortunately I cannot accept. Thank you! I’m currently working part time as a receptionist that allows me lots of flexibility to make time for your furry friends! I can spend nights if needed, and I also drive. I will always go over specific instructions with you as a home owner to make sure everything is in check before leaving your pet in my caring hands. I will constantly keep you updated on your pets status, how they are doing, and even if you want to video chat your furry friend to say hello, that is great too!

Sitter Profile Image: Ann N.
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Ann N.
$67
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
15 years of experience
Winnipeg, MB, R3H

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: Anna P.
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Anna P.
$73
total per night
5.0 out of 5 stars
5 reviews
2 repeat clients
14 years of experience
Winnipeg, MB, R3R

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

Sitter Profile Image: Jessa J.
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Jessa J.
$62
total per night
5.0 out of 5 stars
21 reviews
9 repeat clients
5 years of experience
Winnipeg, MB, R2G

We had Jessa stay in our home for 3 days and nights with our two dogs. They were well looked after, the house was in good shape and she sent daily photos and updates. I would gladly use her again and recommend her to anyone.

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Rosemarie H.
Sitter Profile Image: Arissa R.
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Arissa R.
Star Sitter
$111
total per night
5.0 out of 5 stars
33 reviews
7 repeat clients
16 years of experience
Winnipeg, MB, R3L

10/10 recommended!! Arissa made leaving our dog so smooth!! She took great care of him and kept me updated the whole time!! She loved him and all his corks!! Always scary leaving your pet but she did an awesome job!

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Ashleigh L.
Sitter Profile Image: Olly T.
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Olly T.
$73
total per night
5.0 out of 5 stars
12 reviews
2 repeat clients
15 years of experience
Winnipeg, MB, R3R

Wonderful pet sitter. Dogs loved him. Reliable and trustworthy. You won't be disappointed.

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Vivian W.
Sitter Profile Image: Tanya G.
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Tanya G.
$58
total per night
5.0 out of 5 stars
2 reviews
15 years of experience
Winnipeg, MB, R3N

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

Sitter Profile Image: Hayley B.
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Hayley B.
$45
total per night
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: Cindy H.
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Cindy H.
$84
total per night
5.0 out of 5 stars
6 reviews
20 years of experience
Winnipeg, MB, R3T

Cindy was *phenomenal*. I was on an extremely stressful trip and she was so communicative and send so many pics of my crew, it was a huge weight off my mind to not have to worry about them. She dealt with my reactive dog and shy cats with understanding, empathy, and competence and was an absolute lifesaver when a cancelled flight and some other issues caused delays. Will definitely book Cindy again if she's willing and available the next time I travel!

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Jill S.
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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

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

  • 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.

Meet local sitters who will treat your pets like family

  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

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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 for House Sitting in Headingley on Rover is $44.4 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .

As of August 2026, there are 233 sitters on Rover offering House Sitting across Headingley. Enter your postal code to see which available sitters are closest to your home.

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.

Tip: 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, identity 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 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.

Emergency support is available by phone or email in English 24/7. When an incident occurs, we recommend that sitters contact our Trust & Safety team immediately so that they can connect your sitter with a veterinary professional or offer other resources to help.

If a sitter needs to cancel at the last minute, Rover’s reservation protection means Rover Support will work with you to find a suitable replacement as quickly as possible.

A Meet & Greet is a short introductory meeting between you, your pet, 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.

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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