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
17 repeat clients
16 years of experience
Winnipeg, MB, R3R

Maya enjoyed a lot the stay with Cady and her husband, they were sending us a lot photos and videos to be more comfortable with our baby away. Thanks a lot Cady for all the take care and time with Maya.

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Dienith F.
Sitter Profile Image: Richard & Melissa M.
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Richard & Melissa M.
Star Sitter
$45
total per night
5.0 out of 5 stars
19 reviews
2 repeat clients
20 years of experience
Winnipeg, MB, R3M

I could not have asked for a better pet sitter for Buddy. He was so happy when he arrived home😃☺️Highly recommend Richard and Melissa for boarding/daycare😃

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Amy W.
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

This family is amazing with our dog; he’s always tired out and sorry to leave! We appreciate the personal touches and the energy they bring. He feels right at home which lets us relax knowing he’s in good hands.

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Erin F.
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

Coco had another great stay. As long as they are available they are the only sitter I will use. Coco loves being at their house and they care for her like their own. Thank you!

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Janelle K.
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: Elizabeth V.
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Elizabeth V.
Star Sitter
$37
total per night
5.0 out of 5 stars
19 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: 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

Thank you, Cathy for looking after my girls. They were extremely well taken care of. When I went to pick them up, I felt almost like they didn’t wanna come home. They were having so much fun at auntie Cathy‘s! I’ve used Cathy before and I have not been disappointed. She treats my girls and everyone else’s dog like they’re her own and she loves them just as much. I am extremely grateful that there are people like Cathy out there that I can trust to look after the little loves of my life. Words can’t express how much that means to a pet owners heart, knowing that their littlest family members are being looked after by someone who loves them so much. Thank you, Cathy.

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Michelle P.
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
22 repeat clients
30 years of experience
Winnipeg, MB, R2M

Our third time booking with Colleen - there’s a reason why we keep going back to her. She cares for our dog like her own. There’s really nothing like knowing your pet is in good hands while you’re away. It’s a home away from home! Thank you Colleen and her family for always welcoming Kai into their home.

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

Joshua was wonderful, as always! Anytime he watches my dog, I know she is in good, loving company. Joshua sends daily updates with pictures and answers quickly.

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Alex K.
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 was wonderful with our dog Jules while we were away. She was treated just like one of the family. He sent updates and pictures which was perfect as we missed Jules so much while on vacation. We will definitely book again if and when we go away!

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Amanda E.
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

Dorothea was great and Ernie loved her! She walked him a few times a day and had him play in her yard which he loved. She also sent us photos and videos daily which we appreciated!

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Adrian
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

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!

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

We have had our dog board with Mandy as well as go to her house for daycare. Mandy genuinely loves & cares for our dog as if he was her own. She is reliable and organized as well. We have used Mandy for over a year and she has never once canceled on us. We highly recommend Mandy!

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

Diana and her family took care of our pup for 2 weeks while we were away. She sent so many great pictures of Coco’s adventures with them. They truly took care of Coco like she was their own. Would not hesitate to have Coco stay with this warm and caring family again. Thank you Diana!

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Katherine S.
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

Shuangshuang and her partner watched our 6 month Bichon Frise for a week while we were out of town. This was her second time there and first time overnights. We received tons of pictures and videos daily of her playing with their dogs. Our little Cee-Cee had such a great time. We'd bring her back again for sure!

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Elissa W.
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, R3T

Our dog (Alfie) had a great time with Noshin and her husband! They sent daily pictures and it was evident that Alfie was comfortable with them and was very well taken care of. Feel so happy to have found them! Thanks so much!

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Becca K.
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 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: 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

I couldn’t have asked for better care for Rex. She went above and beyond while watching him, especially when he wasn’t feeling well. She kept me updated throughout his stay, made sure he ate, gave him his probiotics, and even bathed him after he got sick. I really appreciated her communication and how closely she monitored him. It gave me so much peace of mind knowing he was in such caring and capable hands. Rex came home happy, and it’s clear he was treated like family. I would absolutely trust her with him again and highly recommend her to anyone looking for a reliable, compassionate pet sitter.

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Jen e.
Sitter Profile Image: Stephanie O.
Verified Background Check
Stephanie O.
$45
total per night
4.8 out of 5 stars
134 reviews
63 repeat clients
25 years of experience
Winnipeg, MB, R3J

We were so happy Ellie was able to join Stephanie and her fur family. Our 3 weeks away was worry free having Ellie cared for in Stephanie’s private home.

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Brenda G.
Sitter Profile Image: Erin & Mason L.
Erin & Mason L.
Star Sitter
$76
total per night
5.0 out of 5 stars
15 reviews
5 repeat clients
25 years of experience
Winnipeg, MB, R3T

Erin was amazing. She provided lots of updates and made sure to communicate with me or ask questions if needed. She provided lots of exercise and mental stimulation as well. Was super accommodating, polite and just overall a pleasure. My pup had a great time and I would 100% book her again.

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Jennifer E.
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The median cost per night for dog boarding in Headingley is $45

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  • 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

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  • 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
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Popular requests for dog boarding - Headingley

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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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