Pet Boarding Headingley

Find a loving Headingley pet sitter to watch your cat or dog overnight at your sitter’s home.

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Over 119
pet parents in Headingley have booked pet boarding

Headingley, Find top rated pet boarding

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: Pamela H.
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Pamela H.
Star Sitter
$45
total per night
4.9 out of 5 stars
54 reviews
16 repeat clients
14 years of experience
Winnipeg, MB, R2H

Thanks so much again Pam for taking care of Lambros during our vacay. Even buying him boots so you could walk him and also using your baby boy's diaper when Lambros diaper was all consumed. Thank you for all the love for Lambros! We really appreciate it!

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Annabelle R.
Sitter Profile Image: Bibiana R.
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Bibiana R.
Star Sitter
$46
total per night
5.0 out of 5 stars
47 reviews
15 repeat clients
16 years of experience
Winnipeg, MB, R3Y

Bibiana was excellent and so caring during our dog Charlie stay. I would absolutely recommend her and will definitely book with her next time we need sitting for Charlie. Bibiana kept me informed and sent lots of pictures and videos. I felt so comfortable knowing that Charlie was well taken care of.

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Agustina K.
Sitter Profile Image: Oleksandr & Liudmila T.
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Oleksandr & Liudmila T.
$56
total per night
5.0 out of 5 stars
21 reviews
4 repeat clients
15 years of experience
Winnipeg, MB, R3R

Thanks for being such an amazing dog-sitter! I'm sure my pup had a tail-wagging good time with you, and I appreciate your dedication to his well-being. Cj says 5 paws for being his best friend for the week!

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Jessica C.
Sitter Profile Image: Gaia G.
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Gaia G.
$34
total per night
5 years of experience
Winnipeg, MB, R2M

About: Hello everyone! I recently moved to Winnipeg from Italy with my boyfriend and our beloved dog. I've already worked as a dog sitter in Italy and I can't wait to meet your pups here in Canada! My English isn't perfect yet, and I'm studying it diligently every day, but don't worry: the language of the heart and cuddles is universal! I guarantee that every instruction, need, or specific request for your dog will be listened to with the utmost attention and precision. Having a dog myself, I know exactly what it means to love them as family. I will treat your furry little ones with the same dedication, patience, and love I give my own. I'm improving my English, but I'm a very precise person and will use translation tools to ensure | follow all your instructions perfectly.❤️ Your dog will feel very stimulated at my house and will definitely have company, as he can play with my dog, who is very friendly with everyone. I also have a small balcony, so when the weather is nice, we could even sit outside for a bit. I'll let him play. It's also part of my building, and there's a small dog park, so we could easily go down and play a bit there. I also have a kennel and some toys for my dog ​​at home, so everything is already set up to make him feel at home too.❤️ My home is a welcoming place. My apartment is pet-friendly. Pets are more than welcome, and I will, of course, give your pet the utmost attention.

Sitter Profile Image: Anna S.
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Anna S.
Star Sitter
$62
total per night
5.0 out of 5 stars
85 reviews
31 repeat clients
8 years of experience
Winnipeg, MB, R2L

Anna is very nice with our Luke. She made sure that he had his own space to adjust since our cat is not use d to new environment. I will definitely ask her to lookenfor our Luke again.

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Thomas T.
Sitter Profile Image: Jiayi S.
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Jiayi S.
$50
total per night
5.0 out of 5 stars
2 reviews
1 repeat client
7 years of experience
Winnipeg, MB, R3Y

My dog stayed for 5 days and got groomed. She sent me videos and pictures daily and he seemed super happy with her golden retriever and kids. Will definitely leave him with her again! Thank you!

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Kimm P.
Sitter Profile Image: Karen R.
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Karen R.
$23
total per night
5.0 out of 5 stars
46 reviews
17 repeat clients
8 years of experience
Winnipeg, MB, R3J

Karen did a fantastic job with our cat Buttons who is very shy around strangers at first. After a day or so Buttons warmed up to Karens gentle patient demeanor. Plan to use her in future when we require boarding.

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Kyle B.
Sitter Profile Image: Portia G.
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Portia G.
$45
total per night
5.0 out of 5 stars
8 reviews
2 repeat clients
15 years of experience
Winnipeg, MB, R3R

Portia took amazing care of our two dogs. She was super communicative and friendly. Our pups felt comfortable at her house right away and made themselves at home. We would definitely ask Portia to take care of them again. Thank you so much!

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Olivia P.
Sitter Profile Image: Camila C.
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Camila C.
$56
total per night
5.0 out of 5 stars
11 reviews
1 repeat client
10 years of experience
Winnipeg, MB, R3N

Camila took great care of Zarco! He was energetic and happy when I picked him up. She made sure he followed his new diet (despite his protest) which we really appreciated. She also made sure he got lots of love and attention. It was great getting pictures and updates while we were away. We will definitely be using her again for future travels. It was also great that we picked him up and he was nice and tired out and ready for cuddles. He's a bit of a prince and doesn't like to go out in the cold so it is always a trick to keep him exercised when it's cold.

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K D.
Sitter Profile Image: Kendall M.
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Kendall M.
$56
total per night
5.0 out of 5 stars
7 reviews
2 repeat clients
14 years of experience
Winnipeg, MB, R3T

Amazing care. Very very happy with Kendall. Highly recommend

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Brian M.
Sitter Profile Image: Polina B.
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Polina B.
Star Sitter
$50
total per night
5.0 out of 5 stars
54 reviews
19 repeat clients
12 years of experience
Winnipeg, MB, R3C

My cat stayed with Polina for 12 days and he was comfortable and happy throughout. She sent pictures and videos of him daily. She played with him and brushed him and snuggled with him. He came home happy and well cared for. She had all his things (litter box, bowls, etc) clean and ready to go. I would definitely leave him with her again. 😻

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Meghan R.
Sitter Profile Image: Titiksha T.
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Titiksha T.
Star Sitter
$28
total per night
5.0 out of 5 stars
86 reviews
23 repeat clients
10 years of experience
Winnipeg, MB, R3C

When I thought she couldn’t get better she did! Benny remembered her and her husband and was so excited to be back. Leaving him for trips are so hard, but it puts my heart at ease knowing how much he loves them. On top of that I got so many pictures and updates. I always feel very confident that Benny is loved and cared for when staying here. Wouldn’t book any other sitter!!

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Cal S.
Sitter Profile Image: Mary Anne R.
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Mary Anne R.
Star Sitter
$56
total per night
5.0 out of 5 stars
42 reviews
14 repeat clients
50 years of experience
Winnipeg, MB, R3J

Mary Anne was so wonderful with Ollie while we were away! We know our dog is in the best hands when we leave him with her. She looks after every detail to make sure he is happy and eats well. I love the photos we received with comments about each day. I would highly recommend her, and for sure we’ll call her again.

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Ana P.
Sitter Profile Image: Danylo G.
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Danylo G.
$39
total per night
5.0 out of 5 stars
9 reviews
1 repeat client
2 years of experience
Winnipeg, MB, R3B

We cannot say enough wonderful things about Danylo and his wife! From the moment we met, they were warm, professional, and great with our pets. We received regular photo updates that gave us total peace of mind while we were away. They even went above and beyond to buy wet food for my dog as they noticed she didn’t eat much. Thank you for taking great care of Kiwi and Pikachu. We will definitely book with you again soon!

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Amy D.
Sitter Profile Image: Lovepreet B.
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Lovepreet B.
$34
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Winnipeg, MB, R2G

Lovepreet took such great care of Mochi. She made sure he was comfortable the whole stay and sent many pictures and video updates. I would 100% rebook with her!

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Diem My L.
Sitter Profile Image: Amanda H.
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Amanda H.
Star Sitter
$45
total per night
5.0 out of 5 stars
11 reviews
2 repeat clients
10 years of experience
Winnipeg, MB, R3T

Amanda and her two kids took fantastic care of our 4 year old Maltipoo. Right from the time of booking I felt good about leaving our pup with them. We have a very anxious dog who is super nervous and I truly felt like he couldn’t really be in a better space if we had to leave him with someone ☺️ We got daily updates and pictures of his stay which gave us even more reassurance that he was in great care. Highly recommend Amanda and we would definitely rebook when we are back in Winnipeg!

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Jessica S.
Sitter Profile Image: Julius & Glenda R.
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Julius & Glenda R.
$33
total per night
5.0 out of 5 stars
14 reviews
1 repeat client
35 years of experience
Winnipeg, MB, R2P

Our first time using Rover, and Julius and Glenda truly exceeded our expectations! They treated Bella like their own, giving her so much love, attention, and care. It gave us such peace of mind during our vacation knowing she was in such good hands. We couldn’t have asked for a better experience, highly recommend their service to anyone looking for trustworthy and caring sitters!

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Monette R.
Sitter Profile Image: Kyla W.
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Kyla W.
Star Sitter
$39
total per night
5.0 out of 5 stars
4 reviews
3 repeat clients
16 years of experience
Winnipeg, MB, R3J

Kyla was so pleasant and easy to communicate with. My pup Ivy loved her yard and playing with Floyd. Great experience and hope this is one of a few visits for Ivy.

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Delilah B.
Sitter Profile Image: Arissa R.
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Arissa R.
Star Sitter
$62
total per night
5.0 out of 5 stars
33 reviews
7 repeat clients
16 years of experience
Winnipeg, MB, R3L

Another happy sleepover with Arissa. Our pup loves her snuggle time and always comes home happy and healthy. Will book again in the near future!

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Lynda B.
Sitter Profile Image: Catherine E.
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Catherine E.
$45
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
4 years of experience
Winnipeg, MB, R3B

Catherine was very respectful and well mannered. She watched my cat for me and was very responsive on the app and sent photos and asked questions and took great concern in my cat’s comfort and safety. She washed the bowls and litter box I provided and was super nice. I will definitely book with her again.

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Shyanne S.
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The median cost per night for pet boarding in Headingley is $45

Book with peace of mind

  • 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer pet boarding
  2. 2. Meet In Person

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Popular requests for pet boarding - Headingley

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Sitters in Headingley average 6
repeat pet boarding clients

FAQs for Boarding - Headingley

Frequently asked questions about Rover

The average cost for Pet Boarding in Headingley on Rover is $48.84 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 Pet Boarding 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 Pet Boarding. For more information on service fees, click here .

As of August 2026, there are 211 sitters on Rover offering Pet Boarding across Headingley. Enter your postal code to see which available sitters are closest to your home.

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.

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.

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.

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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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.

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