Dog Boarding in Headingley

Find a loving dog boarder to watch your dog overnight at your sitter's home.

Search

More resources

RoverProtect

Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check. Learn more

Loving dog boarding sitters in your neighborhood

Search Results

Sitter Profile Image: Jayson & Lovely M.
Verified Background Check
Sitter Profile Image: Jayson & Lovely M.
Verified Background Check

1. Jayson & Lovely M.

Star Sitter
Your baby will be in good hands
Winnipeg, MB, R2R
16.0 km. away
Boarding, Doggy Day Care
from
$35
per night
5.0 out of 5 stars
39 reviews
8 repeat clients
Profile image

I reached out to them on short notice, requesting their services for the same day, and they promptly accepted. Throughout my 9-day vacation, they provided exceptional care for my dog. Their spacious house and expansive backyard were ideal for my pet, and it was evident that they are true dog lovers. I am extremely satisfied with their services, and without a doubt, they will be my first choice for future dog-sitting needs. Thank you for taking such great care of my furry friend.

Availability updated 4 days ago
Sitter Profile Image: Cady L.
Verified Background Check
Sitter Profile Image: Cady L.
Verified Background Check

2. Cady L.

Star Sitter
Pet Care | Cady & Wen
Winnipeg, MB, R3R
11.4 km. away
Boarding
from
$34
per night
4.9 out of 5 stars
12 reviews
2 repeat clients
Profile image

Our lab stayed with Cady and her husband for a week. They both seemed very happy and confident to care for our large excitable dog. Cady continued to make us feel comfortable by sending pictures and videos throughout the week capturing Bluey’s personality. Although Bluey was excited to be home, I can tell he was happy and enjoyed his time with Cady!!!

Availability updated today
Sitter Profile Image: Cathy M.
Verified Enhanced Background Check
Sitter Profile Image: Cathy M.
Verified Enhanced Background Check

3. Cathy M.

Star Sitter
Let me spoil your fur baby
Winnipeg, MB, R2Y
8.3 km. away
Boarding, Doggy Day Care
from
$50
per night
5.0 out of 5 stars
24 reviews
4 repeat clients
Profile image

Carhy went above and beyond my expectations for following my routine and sending me updates twice a day! My 4 Paps got completely spoiled and loved having her full attention. I would definitely use her services again!

Availability updated 3 days ago
Sitter Profile Image: Polina B.
Verified Enhanced Background Check
Sitter Profile Image: Polina B.
Verified Enhanced Background Check

4. Polina B.

Star Sitter
Cat snuggle corner: play & purr
Winnipeg, MB, R3C
18.4 km. away
Boarding, House Sitting, Drop-In Visits
from
$39
per night
4.9 out of 5 stars
18 reviews
4 repeat clients
Profile image

Very friendly. Sent me photos and updates over the time she was looking after my dog. Great communication to set up weekend with drop off and pick up. Best of all there was no anxiety or decompression with my dog when we got home, who sometimes gets worked up when not with us.

Availability updated today
Sitter Profile Image: Ellen K.
Verified Background Check
Sitter Profile Image: Ellen K.
Verified Background Check

5. Ellen K.

Star Sitter
Tail wagging olympics
Winnipeg, MB, R2H
20.8 km. away
Boarding
from
$40
per night
5.0 out of 5 stars
30 reviews
14 repeat clients
Profile image

Ellen is an excellent sitter. Our active dog was so well looked after and came home happy and tired from playing with Ellen's dog and her other dog guests.

Availability updated 13 days ago
Sitter Profile Image: Bernard M.
Verified Enhanced Background Check
Sitter Profile Image: Bernard M.
Verified Enhanced Background Check

6. Bernard M.

Star Sitter
I really like best friend company
Winnipeg, MB, R3J
10.0 km. away
Boarding
from
$50
per night
5.0 out of 5 stars
18 reviews
5 repeat clients
Profile image

Bernard is great! Very accommodating friendly and great with dogs. Shyloh fell in love with him instantly and you could tell Bernard fell in love with her as well! Bernard sent me a couple pictures and let me know how things were going which helped with my anxiety about leaving Shyloh! But there was no need to worry Bernard took great care of her! Would definitely recommend Bernard to anyone and will hopefully be using him again in the future! :)

Availability updated 48 days ago
Sitter Profile Image: OWEN H.
Verified Enhanced Background Check
Sitter Profile Image: OWEN H.
Verified Enhanced Background Check

7. OWEN H.

Star Sitter
I like big mutts and I cannot lie
Winnipeg, MB, R3R
11.5 km. away
Boarding
from
$45
per night
5.0 out of 5 stars
17 reviews
5 repeat clients
Profile image

Owen is a trustworthy and attentive pet sitter. He truly cared for Gorly and took her on frequent walks, which Gorly absolutely loved. I was impressed by Owen’s fast responses to my messages for updating Gorly’s situation.

Availability updated 19 days ago
Sitter Profile Image: Holly Y.
Verified Background Check
Sitter Profile Image: Holly Y.
Verified Background Check

8. Holly Y.

Rover 101
Stay Pawsitive🐾 Animal Lover💓
winnipeg, MB, R3Y
18.9 km. away
Boarding, Doggy Day Care
from
$51
per night
5.0 out of 5 stars
10 reviews
1 repeat clients
Profile image

First time using Rover and no regrets at all. Choosing Holly as Jolli's sitter is the best decision ever. She sent me photos and videos --- EVERYDAY. She made sure Jolli was happy, comfortable and safe during her stay there. Will definitely book with her again. Jolli also likes her pet Bubu which is a plus. ❤️ Thank you again, Holly! Truly appreciated what you did for us. ❤️

Availability updated 33 days ago
Sitter Profile Image: Francis Ann M.
Verified Background Check
Sitter Profile Image: Francis Ann M.
Verified Background Check

9. Francis Ann M.

Star Sitter
Purr-fect and Trusted Cat Sitter
Winnipeg, MB, R3G
16.5 km. away
Boarding
from
$20
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
Profile image

Francis is always very responsive and provides frequent video and photo updates. She makes sure to take care of anything Leo would need for his stay and he always seems happy to be there.

Availability updated 7 days ago
Sitter Profile Image: Hailey F.
Verified Background Check
Sitter Profile Image: Hailey F.
Verified Background Check

10. Hailey F.

Experienced full time dog sitter🐶
St. Andrews, MB, R1A
34.7 km. away
Boarding
from
$45
per night
5.0 out of 5 stars
7 reviews
1 repeat clients
Profile image

Hailey provided a great temporary home for Ruth, our German Shepherd. She was very accommodating and flexible, allowing us to move drop off and pickup times after our plans changed. We got plenty of updates with pictures and videos and by the looks of it, our dog really enjoyed playing with Hailey's friendly golden retriever. Would definitely recommend!

Availability updated yesterday
Sitter Profile Image: Anna S.
Verified Background Check
Sitter Profile Image: Anna S.
Verified Background Check

11. Anna S.

Star Sitter
Attentive care & a comfy stay!
Winnipeg, MB, R2L
23.3 km. away
Boarding, Doggy Day Care
from
$55
per night
4.9 out of 5 stars
51 reviews
20 repeat clients
Profile image

I highly recommend Anna as a dog sitter! She's kind, caring, and friendly. Anna provided regular updates with pictures, and our dog, Poppy, felt at home with her. It was great to know that Poppy was in good hands and well looked after. The fenced yard was a plus, and it was comforting that Poppy was with a family that was home throughout the day. We felt at ease leaving Poppy with Anna and her family, and we're grateful for their excellent care.

Availability updated today
Sitter Profile Image: Ying N.
Verified Background Check
Sitter Profile Image: Ying N.
Verified Background Check

12. Ying N.

really hope to have the opportunity
winnipeg, MB, R3Y
17.1 km. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
Profile image

Ying was amazing and super response. I can tell Willow really enjoyed her stay with her and had a lot of fun. On top of the great communication, she provided daily updates and pictures of Willow, which I really appreciated! Would definitely book again with her. Thank you so much for everything, Ying!

Availability updated today
Sitter Profile Image: Oleksandr & Liudmila T.
Verified Enhanced Background Check
Sitter Profile Image: Oleksandr & Liudmila T.
Verified Enhanced Background Check

13. Oleksandr & Liudmila T.

Family of pet lovers ❤️
Winnipeg, MB, R3R
8.4 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
Profile image

Going away is so much easier when you know your pet is so well taken care of. My cat, Cooper, had a wonderful stay with Oleksandr and his family!

Availability updated 6 months ago
Sitter Profile Image: Mary Anne R.
Verified Enhanced Background Check
Sitter Profile Image: Mary Anne R.
Verified Enhanced Background Check

14. Mary Anne R.

Rover 101
Star Sitter
Lover of All Animals Large or Small
Winnipeg, MB, R3J
14.2 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$46
per night
4.9 out of 5 stars
19 reviews
9 repeat clients
Profile image

Mary Anne took excellent care of 10 month old Bertie for her first sleepover. I was so grateful to find and book a trusted caregiver for my pup on short notice. Mary Anne was so kind and thoughtful and made us feel at ease through the entire process, from inviting us over for a meet-and-greet the day before, offering flexible drop off and pick up times, and sharing an update on Bertie's visit/care while we were apart. Her space is so welcoming and beautiful, it honestly felt like Bertie was on vacation. It was a really great experience, and I would absolutely not hesitate to recommend Mary Anne's service to others. I will certainly be contacting Mary Anne the next time Bertie needs overnight care!

Availability updated 4 days ago
Sitter Profile Image: Jyoti & Colton P.
Verified Background Check
Sitter Profile Image: Jyoti & Colton P.
Verified Background Check

15. Jyoti & Colton P.

Pup-tastic Dog Sitting!
Winnipeg, MB, R3G
17.1 km. away
Boarding, Doggy Day Care
from
$40
per night
5.0 out of 5 stars
2 reviews
Profile image

Ace had a blast with Jyoti, Colton & Luna! I felt comfortable leaving Ace and they took very good care of him! Loved the videos and pictures with him and Luna. Highly recommended.

Availability updated 5 days ago
Sitter Profile Image: Stephanie O.
Verified Background Check
Sitter Profile Image: Stephanie O.
Verified Background Check

16. Stephanie O.

I Would Care For Animals As My Own!
Winnipeg, MB, R3J
13.6 km. away
Boarding
from
$32
per night
4.9 out of 5 stars
100 reviews
44 repeat clients
Profile image

We got updates and our dog was very happy here. Thank you for being flexible when we ran into issues on our way home. Will definitely use Stephanie again!!

Availability updated yesterday
Sitter Profile Image: Patrick V.
Verified Enhanced Background Check
Sitter Profile Image: Patrick V.
Verified Enhanced Background Check

17. Patrick V.

Star Sitter
Life-long dog (and cat) lover
Winnipeg, MB, R2N
23.4 km. away
Boarding, Doggy Day Care
from
$30
per night
5.0 out of 5 stars
18 reviews
6 repeat clients
Profile image

It was really great to see the concern Patrick had for our dog before agreeing to leave her there. It was also comforting to get regular pictures and updates on who she was doing. There is a whole family supporting stays here which is really nice! 5 stars!

Availability updated yesterday
Sitter Profile Image: Elina A.
Verified Background Check
Sitter Profile Image: Elina A.
Verified Background Check

18. Elina A.

Star Sitter
Experienced pet lovers❤️
Winnipeg, MB, R3Y
17.6 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5.0 out of 5 stars
67 reviews
12 repeat clients
Profile image

Our fiesty pom Taro has been going to Elina and Misha for almost 6 months now and they are the most caring and professional care givers we've ever met. They are absolutely amazing with communication & we can see in Taro's face how much they cared for him everytime. Before with other dog sitters, Taro used to shiver and cry, which made my heart break. When we visit Elina and Misha, Taro wags his tail like a helicopter and gets excited when he hears their names!! Thanks to them we were able to go away for a trip for the first time. They provided several photos and video updates of our baby being pampered with scratches and playtime, and could tell they treated him with love like family.

Availability updated today
Sitter Profile Image: Nilakshi A.
Verified Background Check
Sitter Profile Image: Nilakshi A.
Verified Background Check

19. Nilakshi A.

Star Sitter
Experienced, animal lover
Winnipeg, MB, R3V
21.8 km. away
Boarding, Doggy Day Care, Dog Walking
from
$50
per night
4.9 out of 5 stars
21 reviews
10 repeat clients
Profile image

Nilakshi was fantastic both times our dog stayed with her. Our dog Toba was very comfortable there. She checked in daily with pictures and videos which our kids loved. We will definitely use Nilakshi next time we are in Winnipeg.

Availability updated today
Sitter Profile Image: Paula C.
Verified Background Check
Sitter Profile Image: Paula C.
Verified Background Check

20. Paula C.

Rover 101
Star Sitter
Care For Your Four-legged Friends!
Winnipeg, MB, R3M
18.1 km. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5.0 out of 5 stars
83 reviews
26 repeat clients
Profile image

Paula was amazing with our senior Puggle. We had never left our dog with anyone other then family before and were a little nervous how she would do. Paula gathered all the information about our dogs routine and patterns and things she liked to do and then used this information to make Rosie’s stay at her home like a vacation. We could not have asked for better care. Paula also has a daughter, Emma who was also very attentive to Rosie. From the walks, to the snuggles and extras that Paula provided along with daily communication we could not have been more pleased. The pictures and updates were wonderful and we knew Rosie was enjoying herself just by seeing the pictures. Thank you Paula and Emma we would recommend you to anyone and will certainly use your services again should the need arise!

Availability updated today

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  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!

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 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.

Dog Boarding FAQs

Frequently asked questions about Rover

Connect anywhere with the Rover app