Dog Boarding in Headingley

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Top rated Headingley dog 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: Simone & Adam M.
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Simone & Adam M.
$42
total per night
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Winnipeg, MB, R3Y

Simone & Adam are an absolute dream. From the second we arrived, she was the most welcoming soul. She’d known I was out running around all day, and had snacks ready for me as she knew how busy I was. It melted my soul. Next, my dog Tilly had the best time. She carefully made her so welcome, feel so at home, and kept me updated the entire time. Something popped up and I had to ask them to extend her stay one more night and they were so happy to accept that. I couldn’t recommend them enough. They are beautiful people, with a beautiful home, and the most beautiful energy. I think I’ve found my forever Rover choice!!!

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Britt R.
Sitter Profile Image: Cady L.
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Cady L.
$43
total per night
5.0 out of 5 stars
52 reviews
13 repeat clients
16 years of experience
Winnipeg, MB, R3R

Cady took amazing care of Nashville! I received videos and pictures of him every night which made me feel comfortable on my 10+ days away. He looked so happy. Thank you!!!!!

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Brittany M.
Sitter Profile Image: Joshua V.
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Joshua V.
Star Sitter
$43
total per night
5.0 out of 5 stars
23 reviews
6 repeat clients
6 years of experience
Winnipeg, MB, R3L

We are very satisfied with Joshua! We were anxious as we have a 100lb dog who isn't friendly with strangers and dogs.Joshua very willingly had a meet and greet with us and he was happy to take care of Romeo and the next day we booked a day with Joshua and he handled Romeo extremely well, even when Joshua had his own dog Loki and knowing Romeo has never been with strangers previously.Joshua comes across as caring and responsible person who loves dogs.We are surely looking forward to leave Romeo in Joshuas loving care when we leave for our long vacation! Thank you Joshua.

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samit p.
Sitter Profile Image: Melissa F.
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Melissa F.
Star Sitter
$60
total per night
5.0 out of 5 stars
17 reviews
4 repeat clients
20 years of experience
Winnipeg, MB, R3M

Melissa took wonderful care of Pepita while I was away. She was kind, responsible, and truly attentive to Pepita’s needs, and I could tell from the updates and photos that Pepita felt happy and comfortable with her. It’s clear that Melissa is not only great with pets but also a genuinely good person. I felt completely at ease knowing Pepita was with her, and I would definitely book with her again and highly recommend her to anyone looking for a caring and trustworthy sitter.

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Luis Alberto N.
Sitter Profile Image: Bernard M.
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Bernard M.
Star Sitter
$56
total per night
5.0 out of 5 stars
25 reviews
8 repeat clients
50 years of experience
Winnipeg, MB, R3J

Bella was we’ll taken care of by Bernard. We will definitely consider using him for any future vacations.

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Cheryl M.
Sitter Profile Image: OWEN H.
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OWEN H.
Star Sitter
$56
total per night
5.0 out of 5 stars
24 reviews
6 repeat clients
15 years of experience
Winnipeg, MB, R3R

Owen took care of our adopted 4 yr old Rottie who was very new to us. He communicated with us with pictures and updates every day, and was so patient with our dog who struggles with separation anxiety. Owen’s services were absolutely exceptional. I can’t thank him enough!

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Erika V.
Sitter Profile Image: Noshin A.
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Noshin A.
Star Sitter
$36
total per night
4.9 out of 5 stars
12 reviews
4 repeat clients
6 years of experience
Winnipeg, MB, R3T

Lovely couple! They took great care of Cleo, she clearly enjoyed her time with them! I also appreciate the frequent updates and cute photos from their little adventures ❤️ I would definitely reccomended.

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Katrina F.
Sitter Profile Image: Cathy M.
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Cathy M.
Star Sitter
$56
total per night
5.0 out of 5 stars
43 reviews
9 repeat clients
14 years of experience
Winnipeg, MB, R2Y

Cathy was amazing with our senior dog Binkey. She went over and above with taking care of all his needs!! We were able to enjoy our vacation knowing he was being taken care off. Thank you Cathy!!

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Sean B.
Sitter Profile Image: Colleen C.
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Colleen C.
Star Sitter
$34
total per night
4.9 out of 5 stars
42 reviews
16 repeat clients
30 years of experience
Winnipeg, MB, R2M

Toby’s first Rover adventure was a total success! I was away for five days, and Colleen and her wonderful family made sure my playful, happy puppy felt right at home. Toby absolutely adored their dog Henry. By the end of his stay, he was even grooming him, and Henry was perfectly content to let it happen! When you book with Colleen, you don’t just get one great sitter—you get the whole team. Daughter Sarah was a top-tier cuddler and groomer, and Toby looked thrilled on his walks with Dean and during those cozy nighttime snuggles. Colleen made me feel immediately at ease and never flinched at Toby’s mischievous side (he’s an expert at swiping Kleenex, toilet paper, and the occasional poo bag). She sent plenty of photos and videos, so I could see just how happy he was. I couldn’t have asked for a better experience. Toby came home tired, spoiled, and full of love—clearly, he had the best time.

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Pam S.
Sitter Profile Image: Jayson & Lovely M.
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Jayson & Lovely M.
Star Sitter
$39
total per night
5.0 out of 5 stars
57 reviews
15 repeat clients
3 years of experience
Winnipeg, MB, R2R

We were sent pictures and updates everyday while Kupa was staying with them. They were patient with him as well as he has separation anxiety and it takes time for him to trust. I could tell that he was really cared for during his stay!

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Felicity A.
Sitter Profile Image: Pamela H.
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Pamela H.
Star Sitter
$45
total per night
4.9 out of 5 stars
40 reviews
11 repeat clients
13 years of experience
Winnipeg, MB, R2H

Pamela took excellent care of Pippa. She sent me a video or two everyday and I could see Pippa was playing and being well cared for. I would definitely rebook with Pamela.

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Betty K.
Sitter Profile Image: Ilana A.
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Ilana A.
$45
total per night
5.0 out of 5 stars
13 reviews
1 repeat client
12 years of experience
Winnipeg, MB, R3Y

llana was amazing with my dog. I have never felt such at ease with leaving my sweet girl. She sent me so many photos throughout the day to let me know how she was doing. She is so good at what she does I would highly recommend her and we will definitely be back ☺️

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Alana B.
Sitter Profile Image: Mandy D.
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Mandy D.
Star Sitter
$56
total per night
5.0 out of 5 stars
39 reviews
11 repeat clients
27 years of experience
Winnipeg, MB, R2J

Mandy is fantastic. My dog Fergus was so well taken care of during his 15-day stay. When I dropped Fergus off at Mandy’s he had a sprained back leg. Mandy took great care of him and when I picked him up, he was all healed up. I highly recommend Mandy for your dog sitting and boarding needs. Thanks Mandy!

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Caroline P.
Sitter Profile Image: Ariana R.
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Ariana R.
Star Sitter
$45
total per night
5.0 out of 5 stars
30 reviews
8 repeat clients
5 years of experience
Winnipeg, MB, R3T

Thank you for taking amazing care of our fur baby Bella while we were away for a week! We received tons of pictures and videos update for how Bella is doing and we were so happy to see Bella was in such a great care! Also Ariana and Alison took Bella for many walks, played with her on top of that they took her to a santa clause pictures as well and we cant be more than happy to find such an amazing baby sitter for Bella :) highly recommended to have them watch your fur babies!

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

Athena loved her stay! From the daily updates, I could tell she was happy and well cared for! Athena has a big personality and very loving and shows her way with that but i’m glad she was cared for in her ways she needed! Thanks again and we will be back again!

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Aaron K.
Sitter Profile Image: Mary Anne R.
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Mary Anne R.
Star Sitter
$54
total per night
5.0 out of 5 stars
28 reviews
12 repeat clients
50 years of experience
Winnipeg, MB, R3J

Mary Anne was absolutely amazing with Ollie. We felt very good knowing our “baby” was in her hands. She sent us pictures and comments about Ollie’s activities daily. When we left Ollie, he was a bit scared of the new space, and didn’t want to eat much. Mary Anne was so accommodating when we asked her to boil ann egg for him. With that she won him for the rest of the stay 😄. She even spoiled him, letting him sleep with her! We are planning our next trip and we already booked her again!

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Ana P.
Sitter Profile Image: Titiksha T.
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Titiksha T.
Star Sitter
$27
total per night
5.0 out of 5 stars
56 reviews
14 repeat clients
10 years of experience
Winnipeg, MB, R3C

This is our second time. She always takes amazing care of Milo and Luna. It's always hard to be away from your furry kids, but I have no worries with that. She is knowledgeable about animals and truly cares about your pet.

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Ann C.
Sitter Profile Image: Oleksandr & Liudmila T.
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Oleksandr & Liudmila T.
$56
total per night
5.0 out of 5 stars
17 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: Bibiana R.
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Bibiana R.
Star Sitter
$50
total per night
5.0 out of 5 stars
30 reviews
9 repeat clients
16 years of experience
Winnipeg, MB, R3Y

Bibiana was easy to communicate with and always responded quickly. I appreciate that she was able to look after my dog last minute! She also sent lots of photo/video updates of my pup which I was really happy with. Great experience and would book with her again!

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Stephanie M.
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

Paul was attentive to Meg. She went on walks, played and cuddled. Paul also gave Meg her medication which I was very appreciative. I received pictures and messages which helped ease my mind. Meg loved her visit and I would rebook.

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Jacqueline L.
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The median cost per night for dog boarding in Headingley is $42

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Sitters in Headingley average 6
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Mar 2026, 203 sitters provided dog 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, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 96% of Headingley dog boarding sitters respond in under an hour.

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

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

There are 203 dog boarding sitters in Headingley on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog 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.