Pet Boarding in Headingley

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

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Top rated Headingley pet boarders

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: Birch S.
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Birch S.
$50
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
18 years of experience
Stonewall, MB, R0C

Birch took fantastic care of our dog! It was easy to organize a meet and greet, and she was ready at the organized times. She was thoughtful in her care, taking our dog for lots of walks and giving treats. She also very considerately sewed our dog bed. I would highly recommend her!

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Lindsay N.
Sitter Profile Image: Ranchelle O.
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Ranchelle O.
$50
total per night
4.9 out of 5 stars
70 reviews
26 repeat clients
29 years of experience
Winnipeg, MB, R2R

Very professional and we really appreciated the videos and pictures being sent for updates. We’ll definitely avail of Ranchelle’s services again in the future!

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

Oleksandra and Liudmila took such great care of Atlas for the 3 weeks that we were away. We’re so happy we found such a great family to watch our dog while we’re away. Thank you!

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Kimmy L.
Sitter Profile Image: Jaspreet & Carlos K.
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Jaspreet & Carlos K.
$45
total per night
4.4 out of 5 stars
7 reviews
3 repeat clients
3 years of experience
Winnipeg, MB, R3C

Amazing Sitters!

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Justice A.
Sitter Profile Image: Vladliena M.
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Vladliena M.
$45
total per night
5.0 out of 5 stars
1 review
1 repeat client
12 years of experience
Winnipeg, MB, R3R

Jojo Spent 2 nights with Vlad, she took such great care of my Jojo, made him feel welcome and gave him so much love while I was away. Will definitely board Jojo with Vlad again

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Mercedes H.
Sitter Profile Image: Pamela H.
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Pamela H.
Star Sitter
$45
total per night
4.9 out of 5 stars
46 reviews
14 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: Ariana R.
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Ariana R.
Star Sitter
$45
total per night
5.0 out of 5 stars
36 reviews
11 repeat clients
5 years of experience
Winnipeg, MB, R3T

Ariana took such good care of our Gertie girl while we were away for a week. She checked in daily to let us know how she was doing and even gave our dog her antibiotic ear drops. Our dog got along well with her puppy Spaniel and they spent a lot of time outside in her gated yard. We would definitely use Ariana again!

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Stephanie G.
Sitter Profile Image: Sunisha M.
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Sunisha M.
$56
total per night
5.0 out of 5 stars
19 reviews
3 repeat clients
10 years of experience
Winnipeg, MB, R3Y

Sunisha took great care of my puppy! He is very energetic and can be nervous around new people but she handled him perfectly. She gave regular updates and had great communication.

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Alexandria W.
Sitter Profile Image: Polina B.
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Polina B.
Star Sitter
$50
total per night
5.0 out of 5 stars
49 reviews
18 repeat clients
12 years of experience
Winnipeg, MB, R3C

Very responsible and accommodating! Polina provided the best care of my cat while I was away for 7 days. Her place is spacious and safe for a cat. She sent me daily updates with photos and videos, and I was able to communicate with her easily if I have questions. I would recommend Polina to anyone looking for boarding and I definitely would have her look after my cat in the future.

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HEA IN C.
Sitter Profile Image: Paul S.
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Paul S.
$56
total per night
5.0 out of 5 stars
10 reviews
1 repeat client
20 years of experience
Winnipeg, MB, R2M

This was our first time using Rover, so we were a little nervous on how it would go, but Paul was absolutely fantastic with Gibby, and sent us pictures and updates throughout his 24-hour stay. Gibby was smiling in each picture - living the best doggo life lol 😊. Highly recommend Paul. Also Nice fenced yard for outside time.

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Rachael C.
Sitter Profile Image: Karen R.
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Karen R.
Star Sitter
$23
total per night
5.0 out of 5 stars
45 reviews
14 repeat clients
8 years of experience
Winnipeg, MB, R3J

Will rebook again, and will definitely recommend to friends! Karen took care of our cat in such short notice, sending photos and updates regularly, making us feel less worried leaving for a few days. Our cat seemed really happy with her stay with Karen, she warmed up to her and got comfortable right away. Very satisfied👍

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Vida U.
Sitter Profile Image: Amanda H.
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Amanda H.
$45
total per night
5.0 out of 5 stars
6 reviews
10 years of experience
Winnipeg, MB, R3T

About: Providing a loving place to stay for your pup while you’re away. Experienced pet loving family happy to provide a fun and cozy home away from home. My name is Amanda, I work from home full time and a mom of two animal loving daughters. Our pup Duke is a 2 year old Cavapoo, very submissive and loves to cuddle and play. We love to play fetch and chase in our fully fenced in backyard, go for walks to the park and hang out at home. A great environment for dogs like Duke who do not like being alone! Positive reinforcement, exercise and play have been key for us as pet parents to train and raise our pups. We provide a fully fenced in and secure back yard, strictly on leash in the front and for walks, and a clean homey environment inside. Our dogs have always been treated as family and that includes those we care for while their families are away.

Sitter Profile Image: Taina D.
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Taina D.
$28
total per night
5.0 out of 5 stars
3 reviews
2 years of experience
Winnipeg, MB, R2Y

This was our first time using Rover and booking a pet sitter, and we’re so glad we chose Taina! Our pup clearly had a great time while we were away. We really appreciated the regular updates, photos, and videos. It gave us so much peace of mind. We’ll definitely be booking with Taina again for our next trip. 😊

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Jade O.
Sitter Profile Image: Anghelly A.
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Anghelly A.
Star Sitter
$39
total per night
5.0 out of 5 stars
9 reviews
4 repeat clients
25 years of experience
Winnipeg, MB, R3T

Aspen and Ember had a great stay! Anghelly kept me updated with pictures, throughout! I can tell her and her daughter gave them lots and love and cuddles during their visit!

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Kerstie K.
Sitter Profile Image: Titiksha T.
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Titiksha T.
Star Sitter
$28
total per night
5.0 out of 5 stars
72 reviews
22 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: Tanya G.
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Tanya G.
$47
total per night
5.0 out of 5 stars
2 reviews
15 years of experience
Winnipeg, MB, R3N

Tanya communicated very promptly both pre-booking and during. She sent photos and updates throughout the week which were much appreciated. Would recommend!

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

Omar was amazing! Took great care of Choco and sent pictures and videos of him enjoying his time with Omar. Thank you vert much Omar for everything!

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Perla G.
Sitter Profile Image: Erin L.
Erin L.
Star Sitter
$76
total per night
5.0 out of 5 stars
10 reviews
4 repeat clients
25 years of experience
Winnipeg, MB, R3T

Erin was amazing. She provided lots of updates and made sure to communicate with me or ask questions if needed. She provided lots of exercise and mental stimulation as well. Was super accommodating, polite and just overall a pleasure. My pup had a great time and I would 100% book her again.

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Jennifer E.
Sitter Profile Image: Evan K.
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Evan K.
$67
total per night
5.0 out of 5 stars
36 reviews
9 repeat clients
13 years of experience
West st. Paul, MB, R4A

Evan provided excellent care for Ampersand during her stay with him. She can be pretty anxious in new environments, but she immediately bonded with Evan and felt at ease in his home. We received regular updates with great photos.

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Daniel R.
Sitter Profile Image: Lin L.
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Lin L.
$45
total per night
5.0 out of 5 stars
12 reviews
1 repeat client
17 years of experience
St.Germain South, MB, R5A

Lin took care of my darling really well. She didn’t get fat so I assumed a lot of walking and playing was done. She sent me pictures all the time and I was really very happy my dog is happy with her. There were no issues and she made sure to ask questions. I got my darling back healthy and safe.

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Marie B.
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Over 108
pet parents in Headingley have booked pet boarding

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a boarder who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 pet boarding sitter has to cancel, we’ll work with you to find a new pet boarding sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Headingley average 6
repeat pet boarding clients

Pet Boarding FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for pet boarding in Headingley on Rover as of Jun 2026 was about $45 per night, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

As of Jun 2026, 209 sitters provided pet boarding in Headingley. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, pet boarding sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 97% of Headingley pet boarding sitters respond in under an hour.

Pet boarding sitters with repeat customers have an average of 6 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Headingley.

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

  • Dogs and cats of all ages and abilities, including puppies and kittens
  • Pet parents looking for a safe, loving alternative to a kennel or hotel
  • Pets who’d love to socialize with their sitter’s pets

There are 209 pet boarding sitters in Headingley on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.