Dog Daycare in Headingley

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Top rated Headingley doggy day care sitters

Prices are estimates per day for 1 dog. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Mandy D.
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Mandy D.
Star Sitter
from
$56
per day
5 out of 5.0 stars
32 reviews
5 repeat clients
27 years of experience
Winnipeg, MB, R2J

Wow! My dog had a great day. Mandy did all sorts of activities with him & made sure he was well take care of after his neuter. Will definitely book again with Mandy!

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J Alicia D.
Sitter Profile Image: Bibiana R.
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Bibiana R.
from
$45
per day
5 out of 4.9 stars
21 reviews
4 repeat clients
16 years of experience
Winnipeg, MB, R3Y

Bibiana was really great with Clover and Clover loved staying there and especially playing with her own sweet dog. Very sweet :) Thanks so much!

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Jodi G.
Sitter Profile Image: Obed & Funmi S.
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Obed & Funmi S.
Star Sitter
from
$50
per day
5 out of 5.0 stars
33 reviews
6 repeat clients
10 years of experience
Winnipeg, MB, R3T

Funmi and Obed are wonderful! They looked after my Sunny with doggy daycare twice a week for 6months. Every time I dropped her they greeted us warmly with their lovely family and Sunny ran in every time excited to see them. We’re both going to miss them since we’re moving away. You would be fortunate for them to take care of your loved one 🙌🏻🙏🏻

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Jeannie K.
Sitter Profile Image: Anna S.
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Anna S.
Star Sitter
from
$56
per day
5 out of 5.0 stars
66 reviews
26 repeat clients
8 years of experience
Winnipeg, MB, R2L

Pippa is always happy to spend a day with Anna, who sent me pictures to let me know how Pippa was doing; and was understanding and flexible with my needing to change our pickup time.

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Betty K.
Sitter Profile Image: Arissa R.
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Arissa R.
Star Sitter
from
$42
per day
5 out of 5.0 stars
12 reviews
4 repeat clients
16 years of experience
Winnipeg, MB, R3L

⭐️⭐️⭐️⭐️⭐️ Arissa took such wonderful care of Jax! He’s always so excited to see her and sad to say goodbye. She was warm, attentive, and made him feel right at home- to the point where he barely noticed I arrived because he was too busy having fun and playing with toys. I’d absolutely recommend her to anyone looking for loving, reliable pet care.

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miranda
Sitter Profile Image: Elina A.
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Elina A.
Star Sitter
from
$45
per day
5 out of 5.0 stars
102 reviews
18 repeat clients
20 years of experience
Winnipeg, MB, R3Y

Elina and her husband took great care of Bowski while I was checking out the sights in town. He was happy and tired from playing, looks like me enjoyed his stay! Thanks for the help.

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Diego H.
Sitter Profile Image: Courtney P.
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Courtney P.
from
$36
per day
5 out of 5.0 stars
51 reviews
15 repeat clients
13 years of experience
Winnipeg, MB, R3N

Courtney is so amazing with Barkley. Barkley gets so excited every time we drive down her street to play with her dogs and she comes home tired and well cared for! I would recommend her to everyone I know!

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Jayne S.
Sitter Profile Image: Denis & Stephanie V.
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Denis & Stephanie V.
from
$36
per day
5 out of 5.0 stars
27 reviews
4 repeat clients
40 years of experience
Winnipeg, MB, R3V

Excellent care of my dog. I have peace of mind while he is with Denis and Stephanie

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Janet M.
Sitter Profile Image: Kyla & Marco C.
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Kyla & Marco C.
from
$36
per day
5 out of 5.0 stars
73 reviews
15 repeat clients
14 years of experience
Winnipeg, MB, R2R

Kyla and Isaiah took care of our 4-month old beagle puppy Luna for the day. She had such a good time and loved playing with their dogs despite the size difference between them! Kyla and Isaiah were very knowledgeable about puppies and sent updates throughout the day. This was our first time leaving our puppy for the whole day and it went better than we could have ever expected!

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Jyoti & Colton P.
Sitter Profile Image: Jayson & Lovely M.
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Jayson & Lovely M.
Star Sitter
from
$34
per day
5 out of 5.0 stars
50 reviews
12 repeat clients
3 years of experience
Winnipeg, MB, R2R

Roo had a great time. She played well with Jayson and Lovely’s dogs and enjoyed the fenced yard. Lovely was very mindful of slowly introducing the dogs to ensure a good experience. Roo came home happy and exhausted from a long day of play!

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Ashton S.
Sitter Profile Image: Tenille S.
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Tenille S.
from
$34
per day
5 out of 5.0 stars
5 reviews
30 years of experience
Winnipeg, MB, R2H

Twnille was very welcoming. Our dog was so happy to stay with her! We will absolutely use her again ❤️

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Allie B.
Sitter Profile Image: Claudia S.
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Claudia S.
from
$39
per day
5 out of 5.0 stars
5 reviews
1 repeat clients
5 years of experience
Winnipeg, MB, R3M

Claudia is the best dog trainer in Winnipeg. She has a beautiful dog-friendly home and is very good with them. 100% would recommend.

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Diego C.
Sitter Profile Image: Mary Anne R.
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Mary Anne R.
Star Sitter
from
$38
per day
5 out of 5.0 stars
22 reviews
10 repeat clients
50 years of experience
Winnipeg, MB, R3J

Mary Anne was wonderful. She made our nervous Bella feel right at ease. Mary Anne spent time learning all about Bella and Bella appeared comfortable roaming her home. Mary Anne has a great fenced backyard which I’m sure bella just loved. Thanks so much Mary Anne!!!!! Bella can’t wait to come back.

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Lauren M.
Sitter Profile Image: Ranchelle O.
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Ranchelle O.
Star Sitter
from
$45
per day
5 out of 4.9 stars
63 reviews
25 repeat clients
12 years of experience
Winnipeg, MB, R2R

Ranchelle is so awesome! He really took great care of Khal. He kept us updated with pictures and videos of Khal playing and having so much fun with his 2 furbabies. He made us feel so at ease. We’ll definitely book him again.

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Rochelle C.
Sitter Profile Image: Ana Maria & Johnathon F.
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Ana Maria & Johnathon F.
from
$89
per day
5 out of 5.0 stars
7 reviews
1 repeat clients
20 years of experience
Winnipeg, MB, R3R

Very sweet dog-sitter with a very clean house. Oreo had so much fun in the backyard and most of all, Ana Maria spent so much time with him - she sent plenty of pictures. Highly recommend!

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Julie M.
Sitter Profile Image: Shuangshuang H.
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Shuangshuang H.
from
$45
per day
5 out of 5.0 stars
25 reviews
6 repeat clients
6 years of experience
Winnipeg, MB, R3P

We left our 5 month Bichon Frise with ShuangShuang and her partner. They took excellent care of her. We received lots of pictures and videos. She received lots of play time. We will definitely bring our pup back.

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Elissa W.
Sitter Profile Image: Melanie A.
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Melanie A.
from
$70
per day
5 out of 5.0 stars
6 reviews
40 years of experience
Winnipeg, MB, R3J

About: Welcome to The Elite Doggie House where your Doggie will feel right at home, away from home. If you’re seeking a luxury, personalized, and private Doggie retreat, read on to discover more!! Your Doggie will be treated with the same love and care as if they were my own. Your Doggie will receive one-on-one attention like no other place in town! I limit my care to no more than 4 Doggies at one time. So each one gets the individual attention they deserve. With car rides, trips to the Doggie park and a walk through the Doggie friendly neighborhood throughout the day. I have big comfy chair, couch, or bed for your Doggie to sleep on. You are welcomed to bring your Doggie’s bed if they need the scent of home during their stay. If your Doggie enjoys a brushing or bath, I can do that too. Just bring the brush and shampoo!! Your Doggie is treated like royalty at The Elite Doggie House. It’s all about your Doggie’s wellbeing during their stay. I offer a small, cozy 900 sq ft, home, with a fenced in backyard, that backs onto a field for convenient walks. A safe space to play, relax and socialize. Your Doggie’s experience will be like no other, and one you’ve never SEEN before. With lots of loving sweet kisses, and belly rubs, your Doggie won’t want to leave. Check out the testimonials!! I guarantee you’ll never book anywhere else again. Caring for Doggies is part of my everyday life. I plan my mornings to evenings around walks, feedings and playtime and ensure your Doggie gets the love and attention they need!! This is a unique Doggie Service like no other. You won’t find more interaction with your Doggie and human contact anywhere else. Your Doggie will enjoy BARKING at the squirrels, the rabbits and all the other Doggies walking by! All while sitting at the front door or out at the backyard fence! If your Doggie is enjoying their time and is tired going home to you, then I’ve done my job! My goal is have your Doggie jump for excitement when they hear “Doggie House’!

Sitter Profile Image: Oleksandr & Liudmila T.
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Oleksandr & Liudmila T.
from
$27
per day
5 out of 5.0 stars
16 reviews
4 repeat clients
15 years of experience
Winnipeg, MB, R3R

Thanks Oleksandr and Liudmila! A++.

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Josh H.
Sitter Profile Image: Candice E.
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Candice E.
from
$28
per day
5 out of 5.0 stars
5 reviews
35 years of experience
Winnipeg, MB, R3R

Georgia was very comfortable with Candice and her home. It was great to receive pictures with updates so i could see she was content and happy during her stay. I would 100% recommend and we will be back :)

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Brenda W.
Sitter Profile Image: Orin T.
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Orin T.
from
$50
per day
3 years of experience
Winnipeg, MB, R3K

About: Dog lover with 3+ years of hands-on experience, including raising my own from puppyhood. Calm, caring, and reliable — your pup will feel right at home with me! I'm available throughout the week with at least one day’s notice. Pet care fits easily into my routine, and I always make time to give each pet the love and attention they deserve. I offer a calm, pet-friendly home in a quiet neighborhood with a secure backyard for safe outdoor play and relaxation. Pets are always supervised and cared for with love and attention. I stick to their routine, provide a clean and cozy environment, and make sure they feel safe, relaxed, and at home.

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Prices are estimates per night for 1 dog. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

Sitter Profile Image: Mandy D.
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Sitter Profile Image: Mandy D.
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Mandy D.
Star Sitter

Energetic, trustworthy and reliable
Winnipeg, MB, R2J
22.2 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
$56
total per day
5 out of 5.0 stars
32 reviews
5 repeat clients
Profile image

Wow! My dog had a great day. Mandy did all sorts of activities with him & made sure he was well take care of after his neuter. Will definitely book again with Mandy!

Availability updated today
Sitter Profile Image: Bibiana R.
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Sitter Profile Image: Bibiana R.
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Bibiana R.

❤️Where Every Paw Feels Like Family
Winnipeg, MB, R3Y
17.6 km. away
Boarding, Doggy Day Care
$45
total per day
5 out of 4.9 stars
21 reviews
4 repeat clients
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Bibiana was really great with Clover and Clover loved staying there and especially playing with her own sweet dog. Very sweet :) Thanks so much!

Availability updated 7 days ago
Sitter Profile Image: Obed & Funmi S.
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Sitter Profile Image: Obed & Funmi S.
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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
$50
total per day
5 out of 5.0 stars
33 reviews
6 repeat clients
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Funmi and Obed are wonderful! They looked after my Sunny with doggy daycare twice a week for 6months. Every time I dropped her they greeted us warmly with their lovely family and Sunny ran in every time excited to see them. We’re both going to miss them since we’re moving away. You would be fortunate for them to take care of your loved one 🙌🏻🙏🏻

Availability updated 8 days ago
Confirmed availability for Labour Day Weekend
Sitter Profile Image: Anna S.
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Sitter Profile Image: Anna S.
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Anna S.
Star Sitter

Attentive care & a comfy stay!
Winnipeg, MB, R2L
23.3 km. away
Boarding, Doggy Day Care
$56
total per day
5 out of 5.0 stars
66 reviews
26 repeat clients
Profile image

Pippa is always happy to spend a day with Anna, who sent me pictures to let me know how Pippa was doing; and was understanding and flexible with my needing to change our pickup time.

Availability updated yesterday
Sitter Profile Image: Arissa R.
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Sitter Profile Image: Arissa R.
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Arissa R.
Rover 101
Star Sitter

Your Pet's New Favorite Sitter!
Winnipeg, MB, R3L
19.3 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
$42
total per day
5 out of 5.0 stars
12 reviews
4 repeat clients
Profile image

⭐️⭐️⭐️⭐️⭐️ Arissa took such wonderful care of Jax! He’s always so excited to see her and sad to say goodbye. She was warm, attentive, and made him feel right at home- to the point where he barely noticed I arrived because he was too busy having fun and playing with toys. I’d absolutely recommend her to anyone looking for loving, reliable pet care.

Availability updated yesterday
Sitter Profile Image: Elina A.
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Sitter Profile Image: Elina A.
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Elina A.
Star Sitter

Experienced pet lovers❤️
Winnipeg, MB, R3Y
17.6 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
$45
total per day
5 out of 5.0 stars
102 reviews
18 repeat clients
Profile image

Elina and her husband took great care of Bowski while I was checking out the sights in town. He was happy and tired from playing, looks like me enjoyed his stay! Thanks for the help.

Availability updated today
Confirmed availability for Labour Day Weekend
Sitter Profile Image: Courtney P.
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Sitter Profile Image: Courtney P.
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Courtney P.

24/7 care, no kids, large backyard
Winnipeg, MB, R3N
16.1 km. away
Boarding, Doggy Day Care
$36
total per day
5 out of 5.0 stars
51 reviews
15 repeat clients
Profile image

Courtney is so amazing with Barkley. Barkley gets so excited every time we drive down her street to play with her dogs and she comes home tired and well cared for! I would recommend her to everyone I know!

Availability updated 47 days ago
Sitter Profile Image: Denis & Stephanie V.
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Sitter Profile Image: Denis & Stephanie V.
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Denis & Stephanie V.

25 years in the vet industry!
Winnipeg, MB, R3V
21.0 km. away
Boarding, Doggy Day Care
$36
total per day
5 out of 5.0 stars
27 reviews
4 repeat clients
Profile image

Excellent care of my dog. I have peace of mind while he is with Denis and Stephanie

Availability updated today
Sitter Profile Image: Kyla & Marco C.
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Sitter Profile Image: Kyla & Marco C.
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Kyla & Marco C.
Rover 101

AirBnb for Your Fur Baby ❤️
Winnipeg, MB, R2R
16.0 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
$36
total per day
5 out of 5.0 stars
73 reviews
15 repeat clients
Profile image

Kyla and Isaiah took care of our 4-month old beagle puppy Luna for the day. She had such a good time and loved playing with their dogs despite the size difference between them! Kyla and Isaiah were very knowledgeable about puppies and sent updates throughout the day. This was our first time leaving our puppy for the whole day and it went better than we could have ever expected!

Availability updated today
Sitter Profile Image: Jayson & Lovely M.
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Sitter Profile Image: Jayson & Lovely M.
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Jayson & Lovely M.
Star Sitter

Your baby will be in good hands
Winnipeg, MB, R2R
16.0 km. away
Boarding, Doggy Day Care
$34
total per day
5 out of 5.0 stars
50 reviews
12 repeat clients
Profile image

Roo had a great time. She played well with Jayson and Lovely’s dogs and enjoyed the fenced yard. Lovely was very mindful of slowly introducing the dogs to ensure a good experience. Roo came home happy and exhausted from a long day of play!

Availability updated 4 days ago
Sitter Profile Image: Tenille S.
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Sitter Profile Image: Tenille S.
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Tenille S.

I love dogs!
Winnipeg, MB, R2H
19.8 km. away
Boarding, Doggy Day Care
$34
total per day
5 out of 5.0 stars
5 reviews
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Twnille was very welcoming. Our dog was so happy to stay with her! We will absolutely use her again ❤️

Availability updated 13 days ago
Sitter Profile Image: Claudia S.
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Sitter Profile Image: Claudia S.
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Claudia S.

Paws, Play, and Love in Our home!
Winnipeg, MB, R3M
18.4 km. away
Boarding, Doggy Day Care
$39
total per day
5 out of 5.0 stars
5 reviews
1 repeat clients
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Claudia is the best dog trainer in Winnipeg. She has a beautiful dog-friendly home and is very good with them. 100% would recommend.

Availability updated 10 days ago
Confirmed availability for Labour Day Weekend
Sitter Profile Image: Mary Anne R.
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Sitter Profile Image: Mary Anne R.
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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
$38
total per day
5 out of 5.0 stars
22 reviews
10 repeat clients
Profile image

Mary Anne was wonderful. She made our nervous Bella feel right at ease. Mary Anne spent time learning all about Bella and Bella appeared comfortable roaming her home. Mary Anne has a great fenced backyard which I’m sure bella just loved. Thanks so much Mary Anne!!!!! Bella can’t wait to come back.

Availability updated 4 days ago
Sitter Profile Image: Ranchelle O.
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Sitter Profile Image: Ranchelle O.
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Ranchelle O.
Star Sitter

friendly/safe environment fur all
Winnipeg, MB, R2R
15.3 km. away
Boarding, House Sitting, Doggy Day Care
$45
total per day
5 out of 4.9 stars
63 reviews
25 repeat clients
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Ranchelle is so awesome! He really took great care of Khal. He kept us updated with pictures and videos of Khal playing and having so much fun with his 2 furbabies. He made us feel so at ease. We’ll definitely book him again.

Availability updated 4 days ago
Sitter Profile Image: Ana Maria & Johnathon F.
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Sitter Profile Image: Ana Maria & Johnathon F.
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Ana Maria & Johnathon F.

Hey 💚💙
Winnipeg, MB, R3R
7.0 km. away
Boarding, Doggy Day Care
$89
total per day
5 out of 5.0 stars
7 reviews
1 repeat clients
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Very sweet dog-sitter with a very clean house. Oreo had so much fun in the backyard and most of all, Ana Maria spent so much time with him - she sent plenty of pictures. Highly recommend!

Availability updated today
Confirmed availability for Labour Day Weekend
Sitter Profile Image: Shuangshuang H.
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Sitter Profile Image: Shuangshuang H.
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Shuangshuang H.

Bichon Family Separate room for dog
Winnipeg, MB, R3P
14.1 km. away
Boarding, Doggy Day Care
$45
total per day
5 out of 5.0 stars
25 reviews
6 repeat clients
Profile image

We left our 5 month Bichon Frise with ShuangShuang and her partner. They took excellent care of her. We received lots of pictures and videos. She received lots of play time. We will definitely bring our pup back.

Availability updated 2 days ago
Confirmed availability for Labour Day Weekend
Sitter Profile Image: Melanie A.
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Sitter Profile Image: Melanie A.
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Melanie A.

The Elite Doggie House.
Winnipeg, MB, R3J
11.0 km. away
Boarding, Drop-In Visits, Doggy Day Care
$70
total per day
5 out of 5.0 stars
6 reviews

Melanie is an experienced dog owner who has had numerous dogs. She treats everyones dogs like family. When i went away for a week i left my dog at Melanies and he loved it! He didn’t want to leave! He was spoiled rotten! She has a fenced yard and also loves taking the dogs to the dog park. Your dog will instantly love her! She has a way with dogs. I highly recommend her to care for your dog.

Availability updated yesterday
Sitter Profile Image: Oleksandr & Liudmila T.
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Sitter Profile Image: Oleksandr & Liudmila T.
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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
$27
total per day
5 out of 5.0 stars
16 reviews
4 repeat clients
Profile image

Thanks Oleksandr and Liudmila! A++.

Availability updated over 1 year ago
Confirmed availability for Labour Day Weekend
Sitter Profile Image: Candice E.
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Sitter Profile Image: Candice E.
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Candice E.

Furtastic Home Away From Home
Winnipeg, MB, R3R
7.3 km. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
$28
total per day
5 out of 5.0 stars
5 reviews
Profile image

Georgia was very comfortable with Candice and her home. It was great to receive pictures with updates so i could see she was content and happy during her stay. I would 100% recommend and we will be back :)

Availability updated 20 days ago
Confirmed availability for Labour Day Weekend
Sitter Profile Image: Orin T.
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Sitter Profile Image: Orin T.
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Orin T.

Loving care, as if they were my own
Winnipeg, MB, R3K
7.8 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
$50
total per day
4 reviews

Orin took care of my dog Max while I was away, and I couldn’t have asked for better care!! Thank you so much Orin! Highly recommend!!

Availability updated 4 days ago
Confirmed availability for Labour Day Weekend

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The median cost per day for doggy day care in Headingley is $32

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Sitters in Headingley average 2 repeat doggy day care clients

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