Dog Boarding Headingley

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

Pick up
Search

Over 114
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.
Verified Background Check
Cady L.
Star Sitter
$45
total per night
5.0 out of 5 stars
60 reviews
15 repeat clients
16 years of experience
Winnipeg, MB, R3R

Great home away from home for our dog Ralphie! Cady has great communication, shares lots of pictures and videos. She and her partner are caring, calm and capable! Highly recommend!

Profile image
Emily v.
Sitter Profile Image: Cathy M.
Verified Enhanced Background Check
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

We left Odie with Aunty Cathy for one week while we were on vacation, and she was absolutely wonderful with him. We received multiple pictures, updates, and reassuring confirmations that he was doing well the entire time. Cathy spoiled Odie just as we do. We wouldn’t hesitate to book Aunty Cathy again—in a heartbeat.

Profile image
Diana F.
Sitter Profile Image: Colleen C.
Verified Background Check
Colleen C.
Star Sitter
$34
total per night
4.9 out of 5 stars
59 reviews
20 repeat clients
30 years of experience
Winnipeg, MB, R2M

Lorenzo really enjoyed his stay with Colleen ! She sent pictures and msg everyday to me . Lorenzo looked so happy going for walks and playing . I would definitely leave him with Colleen again . 💕🐶

Profile image
Becky B.
Sitter Profile Image: Jayson & Lovely M.
Verified Background Check
Jayson & Lovely M.
Star Sitter
$39
total per night
5.0 out of 5 stars
60 reviews
15 repeat clients
5 years of experience
Winnipeg, MB, R2R

We received daily updates on Pika’s experience. She received so much love while we were away and Jayson and Lovely accommodated our late pick up. We will book again!

Profile image
Julie H.
Sitter Profile Image: Melissa F.
Verified Background Check
Melissa F.
Star Sitter
$60
total per night
5.0 out of 5 stars
26 reviews
8 repeat clients
20 years of experience
Winnipeg, MB, R3M

Melissa and Oliver took great care of Jesse again! We were very happy they could fit us in and Jesse ran right to their door when we took him out of the car. He's ignoring us today because he had so much fun. Good communication everyday puts us at ease.

Profile image
Bev W.
Sitter Profile Image: Bernard M.
Verified Enhanced Background Check
Bernard M.
Star Sitter
$56
total per night
5.0 out of 5 stars
28 reviews
11 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!

Profile image
Thelma H.
Sitter Profile Image: Joshua V.
Verified Background Check
Joshua V.
Star Sitter
$44
total per night
5.0 out of 5 stars
29 reviews
9 repeat clients
7 years of experience
Winnipeg, MB, R3L

Joshua was fantastic! He took care of my dog Kolsch for a few days while I was on a work trip and Kolsch clearly had lots of fun! I got frequent updates with pictures and videos telling me about how Kolsch was doing and what they were up to, and she got in lots of walks and time outside at the park. Joshua's dog Loki was also a great companion for Kolsch to play with. Joshua was really responsive and kind, and clearly really loves dogs. I knew Kolsch was safe in his home. I will definitely be booking with Joshua again. Thanks for taking such good care of my dog! :)

Profile image
Alex K.
Sitter Profile Image: Simone & Adam M.
Verified Background Check
Simone & Adam M.
$42
total per night
5.0 out of 5 stars
15 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!

Profile image
Muhammad V.
Sitter Profile Image: Diana M.
Verified Background Check
Diana M.
$43
total per night
5.0 out of 5 stars
20 reviews
1 repeat client
15 years of experience
Winnipeg, MB, R3Y

Diana’s was awesome with our two little babies 🦮🐶. She was the only reason we were able to stay calm while being away from them. She kept us informed by sending us photos, videos, and comments of every walk, or fun moment with them. She did a meet and greet previous the boarding which helped me and my husband to feel comfortable, and our doggies just fell in love of her and her beautiful family. I’ll always recommend her for her professionalism and the heart she puts into caring for animals. As long as she is able to, she will be our forever go to petsitter 😊

Profile image
Lissette L.
Sitter Profile Image: Dorotea F.
Verified Background Check
Dorotea F.
Star Sitter
$54
total per night
5.0 out of 5 stars
48 reviews
12 repeat clients
25 years of experience
Winnipeg, MB, R2C

Dorotea takes great care of our pups. They always come home happy and tired. I feel comfortable leaving my babies with her (which is saying a lot).

Profile image
Ange B.
Sitter Profile Image: Shuangshuang H.
Verified Enhanced Background Check
Shuangshuang H.
Star Sitter
$54
total per night
5.0 out of 5 stars
33 reviews
9 repeat clients
8 years of experience
Winnipeg, MB, R3P

Ellice had a wonderful stay, and we couldn’t be happier with the care she received. We appreciated the regular updates and photos, and it was clear that she was treated with kindness and attention. Thank you for taking such good care of her. We would definitely trust you with Ellice again and highly recommend your services.

Profile image
Konstantin B.
Sitter Profile Image: Mandy D.
Verified Background Check
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 is fantastic. My dog Fergus was so well taken care of during his 15-day stay. When I dropped Fergus off at Mandy’s he had a sprained back leg. Mandy took great care of him and when I picked him up, he was all healed up. I highly recommend Mandy for your dog sitting and boarding needs. Thanks Mandy!

Profile image
Caroline P.
Sitter Profile Image: OWEN H.
Verified Enhanced Background Check
OWEN H.
Star Sitter
$56
total per night
5.0 out of 5 stars
26 reviews
7 repeat clients
15 years of experience
Winnipeg, MB, R3R

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.

Profile image
Sharon Y.
Sitter Profile Image: Taina D.
Verified Background Check
Taina D.
$34
total per night
5.0 out of 5 stars
3 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.

Profile image
T R.
Sitter Profile Image: Noshin A.
Verified Background Check
Noshin A.
Star Sitter
$36
total per night
4.9 out of 5 stars
16 reviews
7 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!

Profile image
Benjamin H.
Sitter Profile Image: Tejaswini & Saumik M.
Verified Background Check
Tejaswini & Saumik M.
Star Sitter
$53
total per night
5.0 out of 5 stars
17 reviews
6 repeat clients
5 years of experience
Winnipeg, MB, R2N

Tejaswini and Saumik were the best dog sitters I could ask for, especially on such short notice! My friend was staying with me from out of town but my landlord doesn’t allow any pets so we had to look for a dog sitter within the same day for the weekend. Tejaswini and Saumik were very quick at responding and had been so patient with me since it was my first time booking on this website. Once they talked to my friend, they received his dog shortly after and would send pictures, videos, and updates through the entire weekend. My friends dog was so happy and he had a great time playing with the other dog as well! My friend was turned away by many people because his dog is a mix with a pitbull, which to some people is automatically a no. I’m glad they gave my friends dog a chance cause he’s really sweet and he loved his time with them. Can’t wait to book again!

Profile image
Ian P.
Sitter Profile Image: Amanda H.
Verified Background Check
Amanda H.
$45
total per night
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Winnipeg, MB, R3T

Amanda and her two kids took fantastic care of our 4 year old Maltipoo. Right from the time of booking I felt good about leaving our pup with them. We have a very anxious dog who is super nervous and I truly felt like he couldn’t really be in a better space if we had to leave him with someone ☺️ We got daily updates and pictures of his stay which gave us even more reassurance that he was in great care. Highly recommend Amanda and we would definitely rebook when we are back in Winnipeg!

Profile image
Jessica S.
Sitter Profile Image: Elizabeth V.
Verified Background Check
Elizabeth V.
Star Sitter
$37
total per night
5.0 out of 5 stars
17 reviews
2 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!

Profile image
roxanne D.
Sitter Profile Image: Oleksandr & Liudmila T.
Verified Enhanced Background Check
Oleksandr & Liudmila T.
$56
total per night
5.0 out of 5 stars
19 reviews
4 repeat clients
15 years of experience
Winnipeg, MB, R3R

Oleksandra and Liudmila took such great care of Atlas for the 3 weeks that we were away. We’re so happy we found such a great family to watch our dog while we’re away. Thank you!

Profile image
Kimmy L.
Sitter Profile Image: Anna S.
Verified Background Check
Anna S.
Star Sitter
$62
total per night
5.0 out of 5 stars
83 reviews
31 repeat clients
8 years of experience
Winnipeg, MB, R2L

Anna provided daily pictures and updates on how my dog was settling in. She was well cared for and happy. I felt confident in the care she was receiving.

Profile image
Betty K.
1 / 1
View more sitters

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

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 $49.82 per night (as of July 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 July 2026, there are 200 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge