Dog Boarding Headingley

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Over 118
pet parents in Headingley have booked dog boarding

Headingley, Find top rated dog boarding

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

1 / 1
Sitter Profile Image: Cady L.
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Cady L.
Star Sitter
$45
total per night
5.0 out of 5 stars
61 reviews
16 repeat clients
16 years of experience
Winnipeg, MB, R3R

I left my 75lbs lab for 4 nights but needed to extend a night due to flight home challenges. I received daily photos and videos. Even pics os her cuddling with them! I’ll definitely use them again. ❤️😊

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Tania A.
Sitter Profile Image: Colleen C.
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Colleen C.
Star Sitter
$34
total per night
4.9 out of 5 stars
61 reviews
20 repeat clients
30 years of experience
Winnipeg, MB, R2M

Oh my gawsh, Colleen and her family took such great care of my poodle, it was her home away from home. Seriously the best folks to care for your fur baby! Thank you!

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Charl B.
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
60 reviews
19 repeat clients
5 years of experience
Winnipeg, MB, R2R

Jayson and Lovely are very warm and friendly, and very knowledgeable about small dogs. They took Shadow in like he was their own. They provided daily updates with pics and videos which we really appreciated. We knew Shadow was in good hands, we weren't worried at all!

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

Cathy gives me peace of mind while I am away. I have 1 on medications, so it is important to have a sitter who can continue with your time schedule. My dogs just love going to Auntie Cathy's for a holiday of getting spoiled xoxox

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

Melissa took wonderful care of Pepita while I was away. She was kind, responsible, and truly attentive to Pepita’s needs, and I could tell from the updates and photos that Pepita felt happy and comfortable with her. It’s clear that Melissa is not only great with pets but also a genuinely good person. I felt completely at ease knowing Pepita was with her, and I would definitely book with her again and highly recommend her to anyone looking for a caring and trustworthy sitter.

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Luis Alberto N.
Sitter Profile Image: Richard & Melissa M.
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Richard & Melissa M.
$45
total per night
5.0 out of 5 stars
13 reviews
1 repeat client
20 years of experience
Winnipeg, MB, R3M

I found myself in need of someone to look after Livvy on pretty short notice. I was a little bit worried because she’s not the greatest on leash walker and she’s also never stayed with anybody but friends and family, so staying with a stranger is new to her. Richard and Melissa were great, the first night when she was showing signs of being a little bit anxious they insured that she got out for a decompressing walk and then they took her to an area of the house that was a little less stimulating so she could have some quiet time. Knowing that someone was picking up on her cues was really reassuring for Me and also for Liivvy. They were very communicative the whole time she was staying there making sure that I got photos and they let me know how she was settling in. I would have zero hesitations about recommending them or booking with them again.

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Amy R.
Sitter Profile Image: Dorotea F.
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Dorotea F.
Star Sitter
$54
total per night
5.0 out of 5 stars
50 reviews
12 repeat clients
25 years of experience
Winnipeg, MB, R2C

Dorotea had our puppy for a week while we went on vacation and she went above and beyond to make sure Louie felt comfortable and like he was just at home! She would cook every day meals for our fussy eater and send us numerous updates on their day. Whenever we need care for our baby we always make sure Dorotea is available! I’m pretty sure Louie had more fun on his vacation with Dorotea than we did!! Thank you so so much for your excellent care!

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Lindsay M.
Sitter Profile Image: Joshua V.
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Joshua V.
Star Sitter
$45
total per night
5.0 out of 5 stars
30 reviews
9 repeat clients
7 years of experience
Winnipeg, MB, R3L

Josh and Loki were excellent hosts. He kept us informed and took our dog on lots of walks and trips to the dog park. It was over Christmas and Santa even had a gift for her. We will definitely rebook again.

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Suzie S.
Sitter Profile Image: Mandy D.
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Mandy D.
Star Sitter
$56
total per night
5.0 out of 5 stars
49 reviews
13 repeat clients
27 years of experience
Winnipeg, MB, R2J

Mandy truly loves my puppy and goes to great lengths to provide a stimulating, enjoyable environment for him. I recommend Mandy to anyone looking for excellent pet care.

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J Alicia D.
Sitter Profile Image: Elizabeth V.
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Elizabeth V.
Star Sitter
$37
total per night
5.0 out of 5 stars
17 reviews
3 repeat clients
30 years of experience
Winnipeg, MB, R3P

Elizabeth was fantastic for my senior Yorkie Tinkerbell - regular updates, special accommodations, lots of walks and tinker bell evidently enjoyed her stay!

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roxanne D.
Sitter Profile Image: Diana M.
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Diana M.
$56
total per night
4.9 out of 5 stars
24 reviews
1 repeat client
16 years of experience
Winnipeg, MB, R3Y

Diana and Steven are wonderful people with the kindest souls. My Hagen, due to his lack of experience with children, doesn't get along well with them, but at Diana's house, he fully opened up to the children for the first time, exposing his belly. Regular walks, attention, and care—your pet will feel like he's at summer camp. I highly recommend Diana. Your pet will be happy in good hands.

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Anton S.
Sitter Profile Image: Simone & Adam M.
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Simone & Adam M.
$42
total per night
5.0 out of 5 stars
16 reviews
1 repeat client
10 years of experience
Winnipeg, MB, R3Y

We are incredibly grateful to Simone and Adam for the amazing care they gave our precious kitten, Skye. From the very beginning, we knew she was in loving and caring hands. Simone and Adam treated Skye like she was part of their own family. They gave her so much love, attention, and affection, and the regular updates and photos brought us great peace of mind while we were away. It was clear that Skye was happy, comfortable, and truly cared for. When Skye came home, she was healthy, relaxed, and full of her playful personality. We also want to thank Simone and Adam for the thoughtful gift—it was such a kind and generous surprise. Our children were so happy, and our whole family truly appreciated the gesture. We wholeheartedly recommend Simone and Adam to anyone looking for trustworthy, compassionate, and dedicated pet sitters. Thank you both for treating our little Skye with so much love and care. We couldn’t have asked for better people to look after her, and we will absolutely trust you with her again in the future!

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Muhammad V.
Sitter Profile Image: Shuangshuang H.
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Shuangshuang H.
Star Sitter
$54
total per night
5.0 out of 5 stars
35 reviews
10 repeat clients
8 years of experience
Winnipeg, MB, R3P

I found Shuang Shuang to be a very responsible person who truly enjoys caring for animals. She is very caring and loves playing with my pet PotPot together with her own 2 cute dogs . I would highly recommend her to all. She does a great job and your pet will love her too.She always update me by sending photos of my Potpot. She deserved more than 5 stars. Thanks Shuang Shuang💕

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Ailene C.
Sitter Profile Image: Noshin A.
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Noshin A.
Star Sitter
$36
total per night
4.9 out of 5 stars
17 reviews
9 repeat clients
6 years of experience
Winnipeg, MB, R3T

Noshin provided great care for our two guinea pigs! Easy to communicate with and very responsive. She provided pictures during their care, was flexible with pick up and drop off times and even washed sheets and dropped them off after pick up. Highly recommend! Will definitely rebook again!

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Benjamin H.
Sitter Profile Image: OWEN H.
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OWEN H.
Star Sitter
$56
total per night
5.0 out of 5 stars
27 reviews
7 repeat clients
15 years of experience
Winnipeg, MB, R3R

Owen provided great communication & photos while I was away. He was very relaxed & took extra care regarding allergies for Wyatt. He is clearly very comfortable with dogs which made leaving Wyatt with him easy & stress free!

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Sharon and Micah C.
Sitter Profile Image: Tejaswini & Saumik M.
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Tejaswini & Saumik M.
Star Sitter
$53
total per night
5.0 out of 5 stars
18 reviews
7 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.
Sitter Profile Image: Taina D.
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Taina D.
$34
total per night
5.0 out of 5 stars
5 reviews
2 years of experience
Winnipeg, MB, R2Y

This was our first time using a pet sitter and the experience was awesome. Taina was great! Loved the check ins and picture updates. Will definitely be a repeat customer.

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T 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
12 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: Stephanie O.
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Stephanie O.
$45
total per night
4.8 out of 5 stars
133 reviews
63 repeat clients
25 years of experience
Winnipeg, MB, R3J

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!!

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Kristen C.
Sitter Profile Image: Sunisha M.
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Sunisha M.
$56
total per night
5.0 out of 5 stars
22 reviews
5 repeat clients
10 years of experience
Winnipeg, MB, R3Y

We went away on vacation and Sunisha provided amazing care for Roscoe - providing us multiple photos daily showing how he was settling down and getting comfortable in her home. And when we needed to make alternate arrangements for pickup, she was understanding and flexible. 10/10 would recommend

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Roh A.
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The median cost per night for dog boarding in Headingley is $45

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

Meet local sitters who will treat your dogs like family

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for dog boarding - Headingley

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Headingley average 6
repeat dog boarding clients

FAQs for Boarding - Headingley

Frequently asked questions about Rover

The average cost for Dog Boarding in Headingley on Rover is $49.02 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .

As of August 2026, there are 202 sitters on Rover offering Dog Boarding across Headingley. Enter your postal code to see which available sitters are closest to your home.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Headingley home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you
  • Special instructions such as a list of training cues, medical administration needs, or favourite hang-out spots in your Headingley

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they do not have any disqualifying offences.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

Yes, you can find sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and request a Meet & Greet to walk your sitter through your expectations.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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