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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Sitter Profile Image: Princess O.
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Sitter Profile Image: Princess O.
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21. Princess O.

Rover 101
Star Sitter
Let’s meet the fur besties!!
Winnipeg, MB, R3C
18.5 km. away
Boarding, House Sitting, Doggy Day Care
from
$45
per night
5.0 out of 5 stars
18 reviews
5 repeat clients
Profile image

Princess was an excellent sitter for my dog! You can tell she really loves animals and cares for them greatly and I know my Nala was sad to leave after her stay. She is very flexible, accommodating and texts updates which is great. I would highly recommend and use her again in the future.

Availability updated yesterday
Sitter Profile Image: Anna S.
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Sitter Profile Image: Anna S.
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22. Anna S.

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

Anna was great, it was our first time using the app so we were nervous about leaving Kooper in another home but Anna sent lots of updates and photos throughout the weekend. She let me know that she was watching another dog and the two got along great.

Availability updated 2 days ago
Sitter Profile Image: Ying N.
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Sitter Profile Image: Ying N.
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23. 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
$38
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
Profile image

Ying was so kind and caring towards my cat. My cat has never stayed with a non-family member in 14 years and I can tell she felt so safe with Ying. I appreciated that Ying sent me pictures and messages about my cat throughout thr week. I will book with Ying again in the future for sure ! She was also very accommodating around pick up and drop off times. Thank you Ying!

Availability updated 12 days ago
Sitter Profile Image: Katie S.
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Sitter Profile Image: Katie S.
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24. Katie S.

Social worker and animal lover !
Winnipeg, MB, R3J
13.0 km. away
Boarding, House Sitting
from
$40
per night
1 reviews

I know Katie to be a compassionate and caring human being, who always puts others first (especially animals). She has watched my pets (cat & dog) on multiple occasions and has always treated them as her own!

Availability updated 4 days ago
Sitter Profile Image: Katharine Y.
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Sitter Profile Image: Katharine Y.
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25. Katharine Y.

Star Sitter
A home away from home 🐾🦴
Winnipeg, MB, R2H
21.1 km. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per night
5.0 out of 5 stars
34 reviews
6 repeat clients
Profile image

Katharine did a wonderful job watching our dog for the weekend. She took care of Winnie as if she was her own dog and provided lots of updates and photos. We would feel very comfortable leaving Winnie with her in the future.

Availability updated 18 days ago
Sitter Profile Image: Tim & Amber A.
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Sitter Profile Image: Tim & Amber A.
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26. Tim & Amber A.

Dog Fun, Play, and Stay
Winnipeg, MB, R2M
20.7 km. away
Boarding, Drop-In Visits, Doggy Day Care
from
$48
per night
5.0 out of 5 stars
13 reviews
3 repeat clients
Profile image

Both Tim & Amber were great! They were wonderful sending regular updates with photos & videos. We discussed a couple areas regarding certain habits about Argo. It was positive and showed that they are very caring.

Availability updated 68 days ago
Sitter Profile Image: Denis & Stephanie V.
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Sitter Profile Image: Denis & Stephanie V.
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27. Denis & Stephanie V.

25 years in the vet industry!
Winnipeg, MB, R3V
21.0 km. away
Boarding, Doggy Day Care
from
$44
per night
5.0 out of 5 stars
26 reviews
4 repeat clients
Profile image

Denis and Stephanie watched my foster puppy overnight while I was working a night shift. They’re a very welcoming couple and made the puppy feel right at home at their place. Stephanie worked at a vet clinic for many years and they’re very knowledgeable about animals. I would definitely recommend them for boarding your animal!

Availability updated 5 days ago
Sitter Profile Image: Sunisha M.
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Sitter Profile Image: Sunisha M.
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28. Sunisha M.

Animal lover
Winnipeg, MB, R3Y
18.9 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5.0 out of 5 stars
8 reviews
1 repeat clients
Profile image

Sunisha was an amazing pet sitter. She kept us updated everyday with pictures, and videos with detailed of his day. She asked questions when needed, and supplemented food when our dog was struggling with eating in a new schedule. Our dog also enjoyed playing with ralphie. He was very energetic, and kept our dog entertained for the stay. Overall she was great at communicating and following instructions given at drop off. I would recommend her to friends, and definitely use her services if needed again!

Availability updated 12 days ago
Sitter Profile Image: Obed & Funmi S.
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Sitter Profile Image: Obed & Funmi S.
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29. Obed & Funmi S.

Star Sitter
Caring pet lovers readily available
Winnipeg, MB, R3T
20.4 km. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$48
per night
5.0 out of 5 stars
27 reviews
5 repeat clients
Profile image

From the moment we met Obed and Funmi, it was evident that they possess a genuine love for animals. Their warm and welcoming demeanour immediately put us at ease, reassuring us that Theo would be in safe hands during our absence. They took the time to understand Theo's unique personality, his routines, and any special needs he might have. Throughout the ten days we were away, Obed and Funmi went above and beyond to provide Theo with the utmost care and attention. They maintained his regular feeding schedule, took him on long walks, and engaged him in playtime activities that kept him active and happy. Their dedication to providing a stimulating environment for him was evident in the numerous updates and pictures they sent us regularly, giving us peace of mind and allowing us to feel connected with Theo even from afar. Above all, it was clear that Obed and Funmi treated Theo as a member of their own family. Their genuine affection and care for him were evident in every interaction. They showered him with love and affection, ensuring he felt cherished and content during our absence. Upon returning home, we found Theo in great spirits and happy. It was evident that he had received not just physical care but also the emotional support he needed in our absence. We cannot express enough our appreciation for the exceptional care Obed and Funmi provided. To anyone in need of reliable and compassionate pet sitters, we wholeheartedly recommend Obed and Funmi. Their professionalism, attention to detail, and genuine love for animals make them the ideal choice for anyone seeking exceptional care for their furry companions. We are incredibly grateful for their services and will undoubtedly entrust Theo into their care again in the future. Thank you, Obed and Funmi, for providing such a nurturing and loving environment for Theo. You have truly exceeded our expectations, and we are forever grateful!

Availability updated yesterday
Sitter Profile Image: Meghan P.
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Sitter Profile Image: Meghan P.
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30. Meghan P.

Young professional who loves pets!
Winnipeg, MB, R3G
15.9 km. away
Boarding, Drop-In Visits, Dog Walking
from
$40
per night
8 years of experience

About: I have fostered dogs from northern communities with various behavioural issues - from resource guarding to marking their territory indoors. Now I’m a foster fail with my own northern mutt! I offer a calm, clean, and friendly home for dogs of all sizes. I am currently working full-time on an office/home hybrid schedule. I have the availability to make my own schedule and choose when I work from home. Arrangements can be made should you require consistent supervisor of your pooch, however advance notice is required. I have a friendly and submissive five year old neutered male Shepard/husky mix who would love to play with your dog in our fully fenced in yard! We also typically go for two walks a day around our neighbourhood. When we aren’t outside, my dog and cat enjoy free rein in the house, including on furniture. My cat can be separated from your pet should it be required, with my cat getting the basement and your pet getting to stay upstairs with me.

Availability updated 9 days ago
Sitter Profile Image: Ilana A.
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Sitter Profile Image: Ilana A.
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31. Ilana A.

Rover 101
Star Sitter
❣️Full time dog sitter ❣️
Winnipeg, MB, R2M
22.0 km. away
Boarding, Drop-In Visits, Doggy Day Care
from
$48
per night
5.0 out of 5 stars
102 reviews
37 repeat clients
Profile image

Ilana is the BEST honestly!!! It was the first time our dog slept away from home and we can tell he absolutely enjoyed it. Ilana also provided very wholesome pictures and videos ??????

Availability updated 3 days ago
Sitter Profile Image: Brenna & Ryan W.
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Sitter Profile Image: Brenna & Ryan W.
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32. Brenna & Ryan W.

Dog loving home ready to help!
Winnipeg, MB, R3M
16.7 km. away
Boarding, Dog Walking
from
$40
per night
5.0 out of 5 stars
22 reviews
6 repeat clients
Profile image

Brenna was great with Roger during his 10-day stay. He loved being with her family and had nice walks. Having a backyard was a big plus. I 100% recommend Brenna as a dog sitter.

Availability updated 45 days ago
Sitter Profile Image: Melissa F.
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Sitter Profile Image: Melissa F.
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33. Melissa F.

Love dogs too much to have my own.
Winnipeg, MB, R3M
17.3 km. away
Boarding
from
$50
per night
2 reviews

The Froese family has cared for our 2 year old dog on multiple occasions and has consistently returned her both happy and tired. It is clear they take the time to provide ample exercise to tire out an active pup! They provide a warm and loving home, that our dog eagerly enters upon arrival. The Froese family previously cared for our aging dog, who required a little more patience. They enjoyed slower walks, administered medication as needed, and kept the environment peaceful and familiar to keep our dog at ease. We will continue to utilize their services for years to come!

Availability updated 19 days ago
Sitter Profile Image: Cortney & Mark L.
Sitter Profile Image: Cortney & Mark L.

34. Cortney & Mark L.

Dog Loving Family with 2 Kids
Winnipeg, MB, R3K
7.9 km. away
Boarding
from
$40
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
Profile image

I’m so happy with the care my two dogs received from this amazing family when I was away. They were never short of attention and got spoiled. I will be definitely book again and highly recommend.

Availability updated 3 months ago
Sitter Profile Image: April B.
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Sitter Profile Image: April B.
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35. April B.

Loving and caring home,
Winnipeg, MB, R3T
21.2 km. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5.0 out of 5 stars
8 reviews
Profile image

April was wonderful. Parker was with her for 10 days and we could tell from the pictures we got from April that Parker was having a wonderful time. He got lots of walks and play time. Would definitely book April again.

Availability updated 7 days ago
Sitter Profile Image: Sade O.
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Sitter Profile Image: Sade O.
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36. Sade O.

I'd love to care for your lil loves
Winnipeg, MB, R3G
15.9 km. away
Boarding, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
34 reviews
12 repeat clients
Profile image

My cat has stayed with John and Sade several times. They take such good care of her, she seems relaxed and happy to be there. I highly recommend their services. I appreciated that they were able to be flexible when I had a last minute change. Great about sending pictures regularly and communicating in a timely manner.

Availability updated 2 days ago
Sitter Profile Image: Evan K.
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Sitter Profile Image: Evan K.
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37. Evan K.

Professional Animal Lover
West st. Paul, MB, R4A
26.3 km. away
Boarding, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
28 reviews
6 repeat clients

Evan is the most carrying person and I have so much faith in him that I entrusted him to drive my car and my precious 9 month old dog from BC to Winnipeg and to take care of her for a week until I arrived. He loves all animals and has taken care of his own dogs with love and patience, so I knew he would take care of my girl Chilli. He would send me pictures along their journey and they would both have big smiles on their faces :). Evan did an amazing job looking after Chilli and she was so in love with him after their time together that I can with confidence give him a 100% reference to take care of your dog. Thank you Evan you are the best from Chilli and myself.

Availability updated 60 days ago
Sitter Profile Image: Brock & Nicole U.
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Sitter Profile Image: Brock & Nicole U.
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38. Brock & Nicole U.

Star Sitter
No dog too big or too small
Winnipeg, MB, R2V
24.3 km. away
Boarding, Doggy Day Care
from
$60
per night
5.0 out of 5 stars
26 reviews
5 repeat clients
Profile image

This was my first time using Rover and boarding my very anxious dog. I was nervous to leave him in a new environment, but he settled right in to Brock and Nicole’s home. They made sure he was comfortable the whole weekend and sent lots of photo updates! He had so much fun and we will definitely be booking with them again!!

Availability updated 2 days ago
Sitter Profile Image: Azariah B.
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Sitter Profile Image: Azariah B.
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39. Azariah B.

🌈Doggy Boarding & More!!🐶
Winnipeg, MB, R2W
21.4 km. away
Boarding, House Sitting, Doggy Day Care
from
$40
per night
5.0 out of 5 stars
21 reviews
4 repeat clients
Profile image

Azzy and Annick were amazing caring for our three fur babies. We got updates throughout the date and they were accommodating to our needs. Our dogs were happy to play with Copie and looks like they will have a new bestie. Thanks again for caring for our babies!!!

Availability updated 2 days ago
Sitter Profile Image: Marcus & Meghan F.
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Sitter Profile Image: Marcus & Meghan F.
Verified Enhanced Background Check

40. Marcus & Meghan F.

Active family that loves dogs!
Winnipeg, MB, R2L
21.4 km. away
Boarding
from
$45
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
Profile image

Marcus and Meghan and their children gave Saoirse such wonderful, loving care during her 3-week stay. She got lots of cuddles and was treated like one of the family. They sent us pictures and updates almost every day so we felt very comfortable knowing Saoirse was in good hands. We highly recommend them and will certainly use them again in the future.

Availability updated 4 days ago

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