Dog Boarding Headingley

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

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Over 119
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: Richard & Melissa M.
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Richard & Melissa M.
Star Sitter
$50
total per night
5.0 out of 5 stars
24 reviews
9 repeat clients
20 years of experience
Winnipeg, MB, R3M

Sugar had a great time with Richard and Melissa. She was a little nervous at first, but they gave her lots of TLC and she was soon feeling right at home. I received regular updates and some great photos. They were very patient and understanding and even invited Sugar to come back again. Thanks so much!

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

Our lab had another great stay with Cady and her husband. She is happy to be with them, like her second home when we are away. We are grateful for Cady's care!

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Kimberly W.
Sitter Profile Image: Joshua V.
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Joshua V.
Star Sitter
$45
total per night
5.0 out of 5 stars
33 reviews
10 repeat clients
7 years of experience
Winnipeg, MB, R3L

Joshua took really good care of my baby Tofu! They went on at least 2 walks a day and my dog was also really happy to spend time with his dog Loki. I got updates almost everyday which was very reassuring knowing that Tofu was having a good time. Definitely will book again with Joshua....a real star dog sitter!

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Sheila A.
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
63 reviews
20 repeat clients
5 years of experience
Winnipeg, MB, R2R

Jayson and Lovely were excellent caregivers for our dog. They have a great house with lots of room to roam, excellent communication including pictures, and most importantly, they gave regular care and attention. We would highly recommend them.

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Raymond K.
Sitter Profile Image: Elizabeth V.
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Elizabeth V.
Star Sitter
$37
total per night
5.0 out of 5 stars
21 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: 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: Colleen C.
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Colleen C.
Star Sitter
$34
total per night
5.0 out of 5 stars
64 reviews
22 repeat clients
30 years of experience
Winnipeg, MB, R2M

We’re very fortunate to have found Colleen. This is our second time booking with her. She takes such good care of our boy and genuinely loves him. It’s also evident that Kai feels completely at home at Colleen’s too. It’s truly a privilege to have Colleen look after our dog while we’re away - we were completely worry free. Kai will be back for sure!

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

This was second time I have left my senior dog with Cathy and, she never fails to deliver the upmost quality and care. Our dog is so comfortable in Cathy's care and it puts me at ease. Thank you so much Cathy!

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Kyra G.
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
20 reviews
7 repeat clients
5 years of experience
Winnipeg, MB, R2N

This was the first time we have ever left Koya with someone, and we were a little nervous that she would struggle. She is an anxious dog, and has a history of not eating well. Tejaswini and Sainik were absolutely incredible! She was extremely comfortable with them, and was happy, and played with the other dogs. She ate well, and didn't seem stressed at all. When we went to pick her up, she want even eager to leave. They kept us extremely well informed about what was going on with her, and we felt 100% comfortable the entire time. Thank you so much for taking such great care of our Koya!

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Connie B.
Sitter Profile Image: Diana M.
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Diana M.
$56
total per night
4.9 out of 5 stars
27 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.
$50
total per night
5.0 out of 5 stars
19 reviews
2 repeat clients
10 years of experience
Winnipeg, MB, R3Y

We couldn’t have asked for better caregivers for our dog. Simone and Adam took such amazing care of our dog while we were away — truly above and beyond. They sent frequent updates and photos, which gave us so much peace of mind and always made us smile. It was clear he was happy, comfortable, and treated like part of their family. They handled everything with kindness, patience, and genuine love for animals. We wouldn’t hesitate for a second to have him stay with them again. Knowing he’s in such good hands makes traveling so much easier. Highly, highly recommend!!

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Natalia M.
Sitter Profile Image: Dorotea F.
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Dorotea F.
Star Sitter
$54
total per night
5.0 out of 5 stars
51 reviews
13 repeat clients
25 years of experience
Winnipeg, MB, R2C

This was my second time using Rover, and I was in a bit of a bind. I usually keep my boy Patch at home in Berens with a sitter - he is a playful country boy and a big suck who likes his routines - but everyone was busy. I found Dorotea on River, and she was wonderful from the start. She had me bring Patch and myself in so she could get to know the both of us, learn his routines, and make sure he was comfortable in her home before I left. That meant a lot to me. She kept me well informed with updates and pictures, which gave me real peace of mind while I was away. She gave Patch all the love and attention he deserves, and then some. It’s clear she truly loves animals. I was half joking that Patch might not want to come home with me. This experience allowed me to enjoy my time away without worrying or feeling guilty, because I knew he was in excellent hands. Dorotea was a blessing for Patch and for me, I would trust her again in a heartbeat.

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Angela C.
Sitter Profile Image: Mandy D.
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Mandy D.
Star Sitter
$56
total per night
5.0 out of 5 stars
57 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!

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Caroline P.
Sitter Profile Image: OWEN H.
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OWEN H.
Star Sitter
$56
total per night
5.0 out of 5 stars
28 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.

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Sharon Y.
Sitter Profile Image: Noshin A.
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Noshin A.
Star Sitter
$36
total per night
4.9 out of 5 stars
19 reviews
9 repeat clients
6 years of experience
Winnipeg, MB, R3Y

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

Excellent service!! I am very happy that I chose you as Max's sitter, I received a large number of photos and videos showing the entire adaptation process, without a doubt Max was at home, he also managed to socialize very well with Meimei who is an excellent hostess . 100% recommended and I would definitely use it again.

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Fernando V.
Sitter Profile Image: Danylo G.
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Danylo G.
$45
total per night
5.0 out of 5 stars
12 reviews
1 repeat client
2 years of experience
Winnipeg, MB, R3B

We cannot say enough wonderful things about Danylo and his wife! From the moment we met, they were warm, professional, and great with our pets. We received regular photo updates that gave us total peace of mind while we were away. They even went above and beyond to buy wet food for my dog as they noticed she didn’t eat much. Thank you for taking great care of Kiwi and Pikachu. We will definitely book with you again soon!

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Amy D.
Sitter Profile Image: Bernard M.
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Bernard M.
Star Sitter
$56
total per night
5.0 out of 5 stars
29 reviews
13 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: Jiayi S.
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Jiayi S.
$50
total per night
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
Winnipeg, MB, R3Y

My dog stayed for 5 days and got groomed. She sent me videos and pictures daily and he seemed super happy with her golden retriever and kids. Will definitely leave him with her again! Thank you!

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Kimm P.
Sitter Profile Image: Bibiana R.
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Bibiana R.
Star Sitter
$46
total per night
5.0 out of 5 stars
47 reviews
15 repeat clients
16 years of experience
Winnipeg, MB, R3Y

Bibiana and Cesar were lovely hosts to our Maple. I was initially a bit nervous about using this service (I’d never heard of it until I stumbled accross it while looking for info about local dog kennels) but after a quick online meet I was left feeling confident our girl would be well cared for and in a home environment where she would feel more at home. We were sent many photos of her time with them, which included outings such as walks and car rides. When we picked her up I could see that she was happy and had a fun and relaxing time with them. Thanks again Bibiana and César, your hospitality was very much appreciated and I’m grateful I was able to relax on my vacation knowing she was well cared for. I will be using Rover again!

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Vanessa N.
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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 Dog Boarding - Headingley

Frequently asked questions about Rover

The average cost for Dog Boarding in Headingley on Rover is $48.84 per night (as of September 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 September 2026, there are 197 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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