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: Cady L.
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Cady L.
Star Sitter
$43
total per night
5.0 out of 5 stars
58 reviews
14 repeat clients
16 years of experience
Winnipeg, MB, R3R

Maya enjoyed a lot the stay with Cady and her husband, they were sending us a lot photos and videos to be more comfortable with our baby away. Thanks a lot Cady for all the take care and time with Maya.

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Dienith F.
Sitter Profile Image: Colleen C.
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Colleen C.
Star Sitter
$34
total per night
4.9 out of 5 stars
57 reviews
18 repeat clients
30 years of experience
Winnipeg, MB, R2M

Colleen and her family were so wonderful while I was away for a week! she sent me updates and pictures almost everyday and my dog had a great time while in their care. their home is lovely and I felt she was so welcomed there immediately. I will definitely be using Colleen again!

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Kaitlyn D.
Sitter Profile Image: Simone & Adam M.
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Simone & Adam M.
$42
total per night
5.0 out of 5 stars
14 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: Bernard M.
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Bernard M.
Star Sitter
$56
total per night
5.0 out of 5 stars
28 reviews
11 repeat clients
50 years of experience
Winnipeg, MB, R3J

Ruby & Bernard had a fun couple of days. He was responsive and helpful, his fenced yard is perfect and Ruby was in fine form when I picked her up. We will choose Bernard again!

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Thelma H.
Sitter Profile Image: Melissa F.
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Melissa F.
Star Sitter
$60
total per night
5.0 out of 5 stars
25 reviews
8 repeat clients
20 years of experience
Winnipeg, MB, R3M

This family is amazing with our dog; he’s always tired out and sorry to leave! We appreciate the personal touches and the energy they bring. He feels right at home which lets us relax knowing he’s in good hands.

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

This was Juniors third stay with Cathy. He absolutely adores her as do we. He always has fun and receives top notch care. Thank you for the flexibility on pick up Cathy! Flight delays seem to be inevitable these days. We’ll See you again soon I’m sure. 😊

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Allie K.
Sitter Profile Image: Elizabeth V.
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Elizabeth V.
Star Sitter
$37
total per night
5.0 out of 5 stars
16 reviews
2 repeat clients
30 years of experience
Winnipeg, MB, R3P

Elizabeth was amazing with my dog. She sent regular pictures and updates on how she was doing. She extended hazels stay every time I asked her and she even went out and bought her food. Amazing lady. Definitely recommend

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Donna P.
Sitter Profile Image: Joshua V.
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Joshua V.
Star Sitter
$44
total per night
5.0 out of 5 stars
29 reviews
9 repeat clients
7 years of experience
Winnipeg, MB, R3L

Joshua took really good care of my baby Tofu! They went on at least 2 walks a day and my dog was also really happy to spend time with his dog Loki. I got updates almost everyday which was very reassuring knowing that Tofu was having a good time. Definitely will book again with Joshua....a real star dog sitter!

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Sheila A.
Sitter Profile Image: Noshin A.
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Noshin A.
Star Sitter
$36
total per night
4.9 out of 5 stars
16 reviews
7 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: Shuangshuang H.
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Shuangshuang H.
$54
total per night
5.0 out of 5 stars
31 reviews
9 repeat clients
8 years of experience
Winnipeg, MB, R3P

This is our second time leaving Luna with Shuangshuang. We were very comfortable and knew that our baby bear was in good hands. She sends updates very often and also responds to text quickly. Definitely recommend her services for anyone looking for an awesome sitter!

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Jasper-Karen R.
Sitter Profile Image: Mandy D.
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Mandy D.
Star Sitter
$56
total per night
5.0 out of 5 stars
46 reviews
13 repeat clients
27 years of experience
Winnipeg, MB, R2J

We have had our dog board with Mandy as well as go to her house for daycare. Mandy genuinely loves & cares for our dog as if he was her own. She is reliable and organized as well. We have used Mandy for over a year and she has never once canceled on us. We highly recommend Mandy!

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J Alicia D.
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
59 reviews
15 repeat clients
5 years of experience
Winnipeg, MB, R2R

Jayson and Lovely were excellent caregivers for our dog. They have a great house with lots of room to roam, excellent communication including pictures, and most importantly, they gave regular care and attention. We would highly recommend them.

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Raymond K.
Sitter Profile Image: OWEN H.
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OWEN H.
$56
total per night
5.0 out of 5 stars
25 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: Dorotea F.
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Dorotea F.
Star Sitter
$54
total per night
5.0 out of 5 stars
42 reviews
10 repeat clients
25 years of experience
Winnipeg, MB, R2C

Dorotea went above and beyond with my little Larry! She loved him like her own! He was so comfortable with his first stay away from home! I was very nervous and she put my mind at ease immediately! The updated pictures and videos were priceless. I would highly recommend Dorotea, you can tell she loves what she does. Larry will be looking forward to future visits with his new friend.

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Linda A.
Sitter Profile Image: Arleene Q.
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Arleene Q.
$34
total per night
5.0 out of 5 stars
11 reviews
4 repeat clients
20 years of experience
Winnipeg, MB, R2C

It was our first time using Rover, and Arleene was an amazing host to our little man, Max. She was very knowledgeable, reliable, understanding, a great communicator, and a clear animal lover. From the start, she was incredibly flexible and understanding with pickup and drop-off times. We had initially booked for 8 days, but our return flight was cancelled and we had to extend Max’s stay by one more day. Arleene was thankfully available and accepted our last-minute request, which helped us tremendously—we didn’t have to worry about our fur baby during an already stressful time. Arleene provided detailed daily updates, including Max’s feeding and water intake, litter usage, and general behaviour. She was very attentive to his needs and helped him adjust as smoothly as possible and at his own pace. For example, she noticed that Max was easily scared by noises in the living room, so she prepared a smaller, quieter room where he could hide if needed. In addition to the updates, she sent multiple pictures and videos—even within an hour of dropping him off—which really reassured us that he was in excellent hands. Arleene followed all of Max’s care instructions, and although he is very skittish, he became comfortable with her in just a day or so. That alone shows how warm and attentive her care truly is. Arleene cared for Max as if he were her own, and we would 100% book her again for our next vacation. We highly recommend her to all pawrents who want excellent care for their fur babies! 😊

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Hanna M.
Sitter Profile Image: Diana M.
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Diana M.
$39
total per night
5.0 out of 5 stars
9 reviews
15 years of experience
Winnipeg, MB, R3Y

Diana’s was awesome with our two little babies 🦮🐶. She was the only reason we were able to stay calm while being away from them. She kept us informed by sending us photos, videos, and comments of every walk, or fun moment with them. She did a meet and greet previous the boarding which helped me and my husband to feel comfortable, and our doggies just fell in love of her and her beautiful family. I’ll always recommend her for her professionalism and the heart she puts into caring for animals. As long as she is able to, she will be our forever go to petsitter 😊

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

Anna was very relaxed with my dog Obie. She gave him lots of outdoor play and was understanding of his bedtime nervousness. I would recommend Anna to others and book with her again.

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

Miguel & Salsa had the absolute best time with Bibiana and her husband. She took the best care of my "kids" and frequently updated me each day! She treated them as her own and accommodated to the needs, love and care that they would receive if they were at home. They even spent a day at the beach.. so spoilt! Will be booking with her again!!

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Anna W.
Sitter Profile Image: Stephanie O.
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Stephanie O.
$45
total per night
4.8 out of 5 stars
127 reviews
61 repeat clients
25 years of experience
Winnipeg, MB, R3J

Stephanie is a sweetheart, she handled Coach so nicely, i cannot thank her enough, i went out of country and had to delay my return but Stephanie was so cooperative with all the adjustments. Coach has loved his time with her for about 1 month and a few days, he seemed happy when we picked him up too. Highly recommend to book with her if you want your baby to be taken care in the best possible way.

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Vinca S.
Sitter Profile Image: Tejaswini & Saumik M.
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Tejaswini & Saumik M.
Star Sitter
$56
total per night
5.0 out of 5 stars
17 reviews
5 repeat clients
5 years of experience
Winnipeg, MB, R2N

This was our first time using Rover in Winnipeg, and we had a wonderful experience with Tejaswini and Saumik. They were quick to respond, communicative, and made us feel completely at ease during the meet and greet. Their pup, Stewart, is a sweetheart, and he and Happy got along really well. We had a few last-minute changes to the pickup time, and they were extremely accommodating and understanding. Throughout Happy’s stay, we received regular updates and messages, which reassured us that he was in great hands. It truly felt like Happy was treated as part of their family and was just as comfortable as he would be at home. When we came to pick him up, Happy was actually a little sad to leave Stewart and the other pup behind! We would highly recommend Tejaswini and Saumik to anyone looking for reliable, caring pet sitters who will treat your pet like their own. We’ll definitely be happy to leave Happy with them again in the future!

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Pratik B.
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How Rover works

  1. 1. Search

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  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 dog boarding in Headingley is $45

Why Choose Rover?

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

  • Reservation protection

    It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

  • World-class support

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

Sitters in Headingley average 6
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, 209 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, 97% 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 209 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.