Dog Daycare in Headingley

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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 and includes a booking fee of 11%.

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Sitter Profile Image: Michelle L.
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Michelle L.
$28
total per day
20 years of experience
Headingley, MB, R4H

About: Welcome to Our Home! Hi there! I’m Michelle. I am a stay-at-home mom and lifelong animal lover. With my kids in school full time, I now have extra time and energy to care for your beloved pets. We have two friendly dogs, Pebbles and Archie, who love making new friends. Our home is warm, safe, and full of love so it is the perfect place for your pup to feel comfortable and cared for while you’re away. Whether your dog enjoys playtime or just some quiet cuddle time, I’ll make sure they’re treated like part of our family. I understand how important it is to know your pet is in good hands so I’ll always provide updates and photos to give you peace of mind. I can’t wait to meet you and your furry family member! 🐶💛 I am a stay-at-home mom with two school age kids. So I am always around to keep the dogs company and my kids have been around dogs since they were babies. I have a fenced yard and two dogs to keep your dog company. If your dog is crate trained I can accommodate that as well.

Sitter Profile Image: Melanie A.
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Melanie A.
$85
total per day
5.0 out of 5 stars
9 reviews
1 repeat client
40 years of experience
Winnipeg, MB, R3J

She cared for Nia with the same love and attention one would give to their own dog. Throughout her time with Nia, Melanie consistently kept us updated on her activities, which gave us peace of mind and confidence in the quality of care being provided. Melanie is exceptionally kind, has a natural love for dogs, and communicates with ease and clarity. Her professionalism, reliability, and genuine compassion make her an outstanding caregiver. I highly recommend Melanie to anyone seeking someone trustworthy and dedicated to the well-being of their pets.

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Ferdinand P.
Sitter Profile Image: Bibiana R.
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Bibiana R.
Star Sitter
$50
total per day
5.0 out of 5 stars
30 reviews
9 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: Mary Anne R.
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Mary Anne R.
Star Sitter
$39
total per day
5.0 out of 5 stars
29 reviews
12 repeat clients
50 years of experience
Winnipeg, MB, R3J

Was so sweet & gentle with my little guy. He seemed like he had a great time & was ready for a nap after some play time with his new furry friends. Thank you again! 💛

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Lissa P.
Sitter Profile Image: Oleksandr & Liudmila T.
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Oleksandr & Liudmila T.
$27
total per day
5.0 out of 5 stars
18 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: Courtney P.
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Courtney P.
$36
total per day
5.0 out of 5 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: Elina A.
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Elina A.
Star Sitter
$45
total per day
5.0 out of 5 stars
116 reviews
21 repeat clients
20 years of experience
Winnipeg, MB, R3Y

We were in a tough spot and Elina and her husband took Lola in with open arms for the whole day! They sent updated pics and made us feel at ease… when we picked her up it was like she couldn’t have cared lol she was ever so content!!! Highly recommended!!

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Danielle L.
Sitter Profile Image: Orin T.
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Orin T.
$50
total per day
4.3 out of 5 stars
11 reviews
1 repeat client
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.

Sitter Profile Image: Obed & Funmi S.
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Obed & Funmi S.
Star Sitter
$50
total per day
5.0 out of 5 stars
43 reviews
8 repeat clients
10 years of experience
Winnipeg, MB, R3T

This was my first time leaving Darchin with Obed and Funmi, and they were absolutely lovely and kind. I would happily leave Darchin with them again!

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Sahar S.
Sitter Profile Image: Summer R.
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Summer R.
$45
total per day
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Winnipeg, MB, R3J

I had an amazing experience with Summer! From the moment I dropped off Frank, I knew he was in great hands. Summer went above and beyond to make sure my dog was comfortable and well cared for, offering regular updates and photos throughout the day. I could tell that Frank happy and relaxed in the photos. If you're looking for a trustworthy, caring, and fun environment for your dog, I highly recommend Summer. Truly five stars

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Zoe D.
Sitter Profile Image: Jayson & Lovely M.
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Jayson & Lovely M.
Star Sitter
$34
total per day
5.0 out of 5 stars
57 reviews
15 repeat clients
3 years of experience
Winnipeg, MB, R2R

Our Loki is always excited to spend the day with Jayson & Lovely. We get photo and video updates throughout his stay and we can see that he feels at home.

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Doyle Felix A.
Sitter Profile Image: Simone & Adam M.
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Simone & Adam M.
$45
total per day
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Winnipeg, MB, R3Y

About: We know how hard it is to trust someone with your baby and we don’t take that responsibility lightly. It even took us a whole year of knowing our own sitter (now friend) before we felt comfortable leaving our pets in their care. It's our duty to make sure your pets are always safe and happy under our care. FYI, we absolutely will use baby voices with your fur babies because we just can’t help ourselves, they’re soo cute! 🥰 Over the years, we’ve cared for many wonderful pets — including two closest to our hearts, a sweet cat named Cubs and an energetic pup named Peke— and we’ve loved every moment of it! Our home has baby gates, a fenced backyard and a cozy balcony, perfect for fresh air and supervised playtime. Cats and dogs make us laugh and smile every single day. Adam and I are always sharing funny and adorable pet videos with each other and we’d love to have another pet of our own someday, but for now, caring for yours feels like the next best thing ❤️. Please note: we’re currently accepting one pet at a time and no puppies at this time. Pets must be potty trained. I work from home and set my own schedule, I can give your pet lots of care, companionship, and supervision throughout the day. My husband Adam joins in the fun when he’s home from work. We’re a true pet-care team! Fexible drop-off and pick up times available. We’re also childfree, so our pets (and yours!) get all our attention. Our home has a fenced yard perfect for playtime. We have dog beds and comfy spots to rest on every floor and water, and plenty of toys to keep everyone entertained. Working from home on my own hours, I’m available 24/7. We also have a couple cameras installed in the house. 🏥👩‍⚕️We have a 24/7 vet clinic 2 minutes from our home in case of any emergency and we’d notify you immediately if anything were to occur. Our pets Hera and Aries are up to date on all of their shots💉. We know communication is key, so we’re happy to send updates, FaceTime videos, and plenty of pics. Whatever you need, whenever you need, to give you true peace of mind. Whether it’s cuddles, walks, or keeping your pet’s routine steady while you’re away, we’re here to make sure they feel loved. ❤️

Sitter Profile Image: Alexandria P.
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Alexandria P.
$56
total per day
5.0 out of 5 stars
13 reviews
3 repeat clients
3 years of experience
Winnipeg, MB, R3L

Thank you so much for being so patient with my dog. His first daycare experience somewhere else was really bad, and he usually has a lot of social anxiety. But with you, he’s so much calmer and even eating normally. I can really see how much effort you put into communicating with him. It means a lot to me — you’re honestly amazing with him.

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Ken L.
Sitter Profile Image: Shubham & Mugdha K.
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Shubham & Mugdha K.
$39
total per day
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Winnipeg, MB, R3J

Shubham and Mugdha were fantastic with Nia. They were attentive, caring, and kept her happy and comfortable the whole time. Their updates gave me real peace of mind, and it was clear Nia felt right at home with them. She has a friend—Raisin, their adorable Goldendoodle—which made her stay even better. Highly recommended!

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Ferdinand P.
Sitter Profile Image: Ranchelle O.
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Ranchelle O.
Star Sitter
$45
total per day
4.9 out of 5 stars
65 reviews
26 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: Shuangshuang H.
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Shuangshuang H.
$45
total per day
5.0 out of 5 stars
29 reviews
8 repeat clients
8 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: Varsha T.
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Varsha T.
$39
total per day
5.0 out of 5 stars
17 reviews
5 repeat clients
15 years of experience
Winnipeg, MB, R3C

Loved this experience. My Peanut was showed lots of love and affection. Varsha is wonderful. It’s so happy to see your furbaby excited to go to a sitters home.

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Rosie L.
Sitter Profile Image: Mandy D.
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Mandy D.
Star Sitter
$56
total per day
5.0 out of 5 stars
39 reviews
11 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: Bethany B.
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Bethany B.
Star Sitter
$56
total per day
5.0 out of 5 stars
7 reviews
3 repeat clients
25 years of experience
WINNIPEG, Winnipeg, MB, R3N

About: When you get to know me you will quickly see I am dedicated to giving pets their best life. I have been a devoted pet parent for over 25 years, my pet care business began in 2015 through 100% referrals, and I joined Rover in 2024. I have cared for many types of pets (cats, dogs, small animals and fish, farm animals) and have provided over a decade of short and long term stays, vacation/luxury house sitting and maintenance. Every pet is family to me, I bring the same commitment to caring for my pet family as I bring to every reservation, and offer customized support. In celebration of my 11 years of pet sitting anniversary, pet parents who reserve their first stay in March will receive a $20 off gift certificate valid for 2026! Limit of 11 vouchers. Reach out for more details, or to schedule a complimentary meet and greet. Pet Care I specialize in private stays, providing dedicated care for one pet family at a time, so pets can enjoy a VIP staycation experience that surpasses standard daycares and kennels. My highest priorities are safety, clear communication, and maintaining the routines and comfort your pets are used to. Care is customized, including house sitting, drop-in visits, private boarding for one pet family at a time, active pets, senior pets, and specialty care such as constant supervision. First time reservations include a consultation call and in-person meet and greet, and all stays include clear terms and conditions, and daily photo or video updates. I provide boarding in South Winnipeg (R3T), and in-home services in Winnipeg, St. Norbert, and Niverville. Cat Care My cat Pixi has been with me since 2009, I treat her like royalty and always give the same level of care to your kitties. Pixi happily stays with my boyfriend and his kitten during reservations. I know from decades of experience with cats that they each have a beautifully unique personality and strong preferences. Cats and dogs naturally warm up to me quickly, with tons of attention and cuddles when they want, keeping their litter/dishes/water fresh and clean, playing with them to keep them entertained, and giving them thoughtful care the way you do. Pricing Prices are firm and apply to standard care, additional costs will be clearly communicated if specialty care is requested. Prices displayed show discounts (up to: 20% off extended stays and 50% off additional pet stays for families with multiple pets), Rover's fees (approx. 25-30% per reservation), and taxes. Quiet Hours Messages after 8pm will be received and responded to after 8am the following day. I have availability for drop in-visits, and stays ranging from daily to full season. I work with many pet parents who love to travel or own vacation homes. I specialize in full-season stays. I prioritize a clean, secure and calm environment. My cat Pixi enjoys staying with my boyfriend and his kitten during reservations. When your pets stay in my home they will enjoy roaming around my condo, playing with the many toys, and going for scenic dog walks every day. I will board only one pet family at a time, up to 3 pets per day - house sitting is preferable for larger families. When I stay in your home I am respectful and responsible. I have housesat many vacation and luxury homes in Manitoba. I prioritize leaving homes as clean as when I arrived, and I often provide add-on property care services when requested.

Sitter Profile Image: Erin L.
Verified Background Check
Erin L.
Star Sitter
$54
total per day
5.0 out of 5 stars
7 reviews
3 repeat clients
25 years of experience
Winnipeg, MB, R3T

About: From befriending every neighbourhood dog as a child to sharing my life with them as an adult, my passion for pets is lifelong. I deeply believe in the bond and safety created through positive, reward-based training and would love to support your goals—just let me know what you’re working on, and I’ll practice it with your pet. Whether it’s Dalmatians, Labs, Retrievers, or a mix, like my own, I tailor activities to each dog's energy and age. With my own active dog, we’re harnessed up for canicross or bikejoring in spring and fall, or hitched to a kick sled in winter. With the right gear, weather never stops our adventures. Care for dogs who need real engagement, not just a place to stay. Your pet's safety and well-being are my top priorities. I'm certified in First Aid for Dogs and Cats through CRCS, so you can feel confident that I'm prepared to handle emergencies calmly and effectively. My guests are cared for like my own family pet. Healthy treats, love and attention, play and rest.

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The median cost per day for doggy day care in Headingley is $35

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Sitters in Headingley average 3
repeat doggy day care clients

Doggy Day Care FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Headingley on Rover as of Mar 2026 was about $35 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

As of Mar 2026, 141 sitters provided doggy day care in Headingley. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care 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, 91% of Headingley sitters offering doggy day care respond in under an hour.

Sitters offering doggy day care with repeat customers have an average of 3 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.

Headingley doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Headingley sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:

  • Puppies and high-energy dogs
  • Dogs with special needs, including seniors
  • Pet parents who work long hours
  • Dogs with separation anxiety

There are 141 sitters offering doggy day care 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 doggy day care 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 doggy day care 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.