Dog Boarding Headingley

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

Pick-Up
Search

Over 86
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.
$45
total per night
5.0 out of 5 stars
• 66 reviews
19 repeat clients
16 years of experience
Winnipeg, MB, R3R

“Cady and Wen are amazing! Atlas loves going to their house! We know that atlas is in great hands when it comes to Cady and we are so thankful for their care of our dog!”

Profile image
Paolo P.
Sitter Profile Image: Richard & Melissa M.
Verified Background Check
Richard & Melissa M.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 41 reviews
12 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😃”

Profile image
Amy W.
Sitter Profile Image: Jayson & Lovely M.
Verified Background Check
Jayson & Lovely M.
Star Sitter
$39
total per night
5.0 out of 5 stars
• 66 reviews
21 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: Cathy M.
Verified Enhanced Background Check
Cathy M.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 55 reviews
12 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: Elizabeth V.
Verified Background Check
Elizabeth V.
Star Sitter
$37
total per night
5.0 out of 5 stars
• 25 reviews
4 repeat clients
30 years of experience
Winnipeg, MB, R3P

“Elizabeth was amazing with my dog. She sent regular pictures and updates on how she was doing. She extended hazels stay every time I asked her and she even went out and bought her food. Amazing lady. Definitely recommend”

Profile image
Donna P.
Sitter Profile Image: Bernard M.
Verified Enhanced Background Check
Bernard M.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 31 reviews
15 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: Diana M.
Verified Background Check
Diana M.
Star Sitter
$56
total per night
4.9 out of 5 stars
• 30 reviews
3 repeat clients
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!”

Profile image
Katherine S.
Sitter Profile Image: Gaia G.
Verified Enhanced Background Check
Gaia G.
$40
total per night
5.0 out of 5 stars
• 17 reviews
2 repeat clients
5 years of experience
Winnipeg, MB, R2M

“I’ve booked with Gaia twice now, and both experiences have been wonderful! She was incredibly attentive and caring with my dog, and I always felt reassured knowing she was in good hands. She sent me regular updates and messages throughout the stay, which I really appreciated because it made being away so much easier. We even ran into a few sensitive situations with my dog (her eye acting weird, and her heat starting unexpectedly) but Gaia was so helpful and supportive! She was very responsive and clearly paid attention to my dog’s needs and comfort. Highly recommend! 😊”

Profile image
Julia P.
Sitter Profile Image: Bibiana R.
Verified Background Check
Bibiana R.
Star Sitter
$46
total per night
5.0 out of 5 stars
• 53 reviews
16 repeat clients
16 years of experience
Winnipeg, MB, R3Y

“Bibiana was an absolutely fantastic dog-sitter for Beckett. We got updates multiple times a day, he seemed to fit in beautifully at their place, and had access to a backyard, plenty of walks, and clearly loads of attention at their home. I would highly recommend Bibiana, and I know that Beckett is looking forward to seeing her again soon!”

Profile image
Stephan E.
Sitter Profile Image: Danylo G.
Verified Background Check
Danylo G.
Star Sitter
$47
total per night
5.0 out of 5 stars
• 17 reviews
2 repeat clients
2 years of experience
Winnipeg, MB, R3B

“Everything went so well! Danylo took great care of Pepper and sent sweet photo updates throughout the day, which gave me complete peace of mind. Highly recommend, and I’d definitely book with him again!”

Profile image
Pauline F.
Sitter Profile Image: Noshin A.
Verified Background Check
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

“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!”

Profile image
Becca K.
Sitter Profile Image: Birch S.
Verified Background Check
Birch S.
$56
total per night
5.0 out of 5 stars
• 5 reviews
2 repeat clients
18 years of experience
Stonewall, MB, R0C

“Birch took fantastic care of our dog! It was easy to organize a meet and greet, and she was ready at the organized times. She was thoughtful in her care, taking our dog for lots of walks and giving treats. She also very considerately sewed our dog bed. I would highly recommend her!”

Profile image
Lindsay N.
Sitter Profile Image: Karen R.
Verified Background Check
Karen R.
$23
total per night
5.0 out of 5 stars
• 48 reviews
17 repeat clients
8 years of experience
Winnipeg, MB, R3J

“Will rebook again, and will definitely recommend to friends! Karen took care of our cat in such short notice, sending photos and updates regularly, making us feel less worried leaving for a few days. Our cat seemed really happy with her stay with Karen, she warmed up to her and got comfortable right away. Very satisfied👍”

Profile image
Vida U.
Sitter Profile Image: Ranchelle O.
Verified Background Check
Ranchelle O.
Star Sitter
$50
total per night
4.9 out of 5 stars
• 73 reviews
28 repeat clients
29 years of experience
Winnipeg, MB, R2R

“Very professional and we really appreciated the videos and pictures being sent for updates. We’ll definitely avail of Ranchelle’s services again in the future!”

Profile image
Raymond R.
Sitter Profile Image: Chelsea S.
Verified Background Check
Chelsea S.
$45
total per night
20 years of experience
St Francois Xavier, MB, R4L

About: I have fostered cats and kittens, dogs and puppies for 2.5 years. I am very familiar with medications, illness, treating wounds, and helping scared animals. I work from home 3 days a week so someone is always home to keep your pet company! I would treat your pet like our pets. I have a GIANT fenced back yard that our dog is free to play in. Rocco wants to be friends with everybody and every dog he meets so your pet would have a playmate. If that’s too much, I can also keep them apart or kennel if that’s what they prefer! We also have a separate sunroom that can is great if your pet prefers some space.

Sitter Profile Image: Lilivett & Avner O.
Verified Background Check
Lilivett & Avner O.
$40
total per night
4 years of experience
Winnipeg, MB, R3P

About: Animals have always been a big part of our family. We’ve raised and cared for multiple dogs over the years with lots of love, and for the past 4 years, we've happily shared our home with our Golden Retriever. We have plenty of experience providing a safe, loving, and attentive environment for any furry guest! Hi! We are an animal-loving couple who work 100% from home. 🏡🐾 Since we spend most of our time at home, your furry friend will never be alone and will receive constant attention, cuddles, and companionship throughout the day. We love playing with dogs, spoiling them, and adapting to their pace and specific needs. We live with our 4-year-old Golden Retriever, who is super friendly, social, and loves making new doggy friends. We have a great location: we live very close to a park, which is ideal for daily walks full of sniffing and fun. Whether your dog loves chasing a ball or prefers long walks, they'll find a safe, happy second home here. We'd love to meet you both! ❤️ We live in a safe apartment, where pets are constantly supervised because we work from home. We ensure secure indoor routines, safe leash walks to the nearby park, and a stress-free environment alongside our friendly Golden Retriever

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

“Going away is so much easier when you know your pet is so well taken care of. My cat, Cooper, had a wonderful stay with Oleksandr and his family!”

Profile image
Danit H.
Sitter Profile Image: Titiksha T.
Verified Enhanced Background Check
Titiksha T.
Star Sitter
$28
total per night
5.0 out of 5 stars
• 91 reviews
25 repeat clients
10 years of experience
Winnipeg, MB, R3C

“My cat was well cared for even though this was the first time she was alone without me. She stresses easy but seemed to be less upset when she got home. Communication response was wuick.”

Profile image
Yvonne B.
Sitter Profile Image: Rosa A.
Verified Background Check
Rosa A.
$34
total per night
5.0 out of 5 stars
• 6 reviews
4 years of experience
Winnipeg, MB, R3C

“Rosa was amazing with Sammy. I cannot thank you enough for making this easy for me and my family. It was my first time having my baby left with anyone other than family so I was very nervous but they were amazing with her.”

Profile image
Sam U.
Sitter Profile Image: Mary Anne R.
Verified Enhanced Background Check
Mary Anne R.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 50 reviews
17 repeat clients
50 years of experience
Winnipeg, MB, R3J

“As soon as we met Mary Anne, we (my furry friend and I) felt very comfortable. This was my family's first trip out of the home since the adoption and knowing that our puppy was in great hands made our little vacation that much more enjoyable. I would highly recommend Mary Anne and will definitely seek her out again!”

Profile image
Brian P.
1 / 1
View more

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.

How to book dog boarding

  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 of Dog Boarding in Headingley is $50 per night as of November 2026. Most bookings cost between $33 and $56 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

sitters in Headingley have an average of 14 years of experience. Each sitter has their own unique experience and skill sets for different types of pets. You can find details of each sitter’s potential certifications and abilities, such as pet first-aid or senior pet experience, listed on their profile. Look at other pet parent reviews and repeat pet parent booking rates for an idea of their pet care exp erience.

Yes, you can find sitters who have experience administering medication or managing dietary requirements. On Rover:

  • 88% of sitters can help with special care needs
  • 92% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, 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 use the Meet & Greet to walk your sitter through your expectations.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

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.

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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

You and your Headingley sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge