Pet Boarding Headingley

Find a loving Headingley pet sitter to watch your cat or dog overnight at your sitter’s home.

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Over 87
pet parents in Headingley have booked pet boarding

Headingley, Find top rated pet 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: Katie S.
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Katie S.
$34
total per night
5.0 out of 5 stars
• 3 reviews
5 years of experience
Winnipeg, MB, R3G

“Katie took care of our Bert really well! Bert even made friends with her dog Fletcher! I highly recommend if you’re in Wolesley area to book her. She was willing to accept us at the very last minute!”

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Mhykk M.
Sitter Profile Image: Katie J.
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Katie J.
Star Sitter
$54
total per night
5.0 out of 5 stars
• 30 reviews
4 repeat clients
30 years of experience
Winnipeg, MB, R3T

“Thank you so much to Katie & Eli! The boys were so well taken care of. They were absolutely pooped last night when we got them...they had so much fun!”

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Sarah B.
Sitter Profile Image: XiaoYu W.
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XiaoYu W.
$62
total per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
13 years of experience
Winnipeg, MB, R3T

About: Pet owner since 2013 with both dogs and cats at home (cockapoo, Labrador, and a cat), all friendly and well-socialized. I have years of experience as a kennel attendant in a boarding and grooming facility, handling daily care and monitoring pets. I’m also a pet groomer, comfortable with dogs of different sizes and temperaments. My partner has experience in a veterinary clinic setting, and together we provide a calm, clean, and reliable environment for pets. Pet care is already part of my daily life since I have pets at home. I’m usually home most of the day, so your pet will have lots of attention and won’t be left alone for long periods. My schedule is flexible, so I can easily follow your pet’s routine for feeding, walks, playtime, and any special needs. At my home, your pet will enjoy: ✅ A calm, clean, and secure environment with a fenced yard ✅ Constant supervision ✅ Flexible feeding, walking, and medication routines ✅ Daily photo updates and check-ins ✅ Outdoor meet & greet first, for a safe and stress-free introduction

Sitter Profile Image: Kuljit & Titiksha S.
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Kuljit & Titiksha S.
Star Sitter
$27
total per night
5.0 out of 5 stars
• 24 reviews
7 repeat clients
10 years of experience
Winnipeg, MB, R3C

“Kuljit and Titiksha were amazing hosts to our two cats! They took really good care of them, even with the our cat’s special diets. Highly recommended and would use again”

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Oscar R.
Sitter Profile Image: Ryan H.
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Ryan H.
Star Sitter
$34
total per night
5.0 out of 5 stars
• 11 reviews
5 repeat clients
6 years of experience
Winnipeg, MB, R3G

“Ryan was very easy to communicate with and went above and beyond what we expected. He asked direct and concise questions about our dog's needs.”

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Delilah B.
Sitter Profile Image: Marcus & Meghan F.
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Marcus & Meghan F.
$67
total per night
5.0 out of 5 stars
• 21 reviews
2 repeat clients
30 years of experience
Winnipeg, MB, R2L

“Marcus and Meghan were terrific and loving caretakers for our beloved dog George. They provided frequent updates and photos and we felt extremely comfortable and confident with the experience. We’ll definitely be booking with the family again!”

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Dern
Sitter Profile Image: Candice E.
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Candice E.
$73
total per night
5.0 out of 5 stars
• 6 reviews
35 years of experience
Winnipeg, MB, R3R

About: Animals are my life. I was raised on a farm with dogs, cats, cattle, and horses. I believe in rescues. I have a 3 1/2 year old German Shepard cross pupper who was a foster fail. I foster for but currently do not have a puppy in my home. Pet care smoothly fits into my daily life. Working from home means I’m always there for your pets, giving them all the attention they deserve. I have a large fenced yard for fur babies to run and play. I also provide a crate your dog to sleep in at night if required.

Sitter Profile Image: Brock & Nicole U.
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Brock & Nicole U.
Star Sitter
$73
total per night
5.0 out of 5 stars
• 48 reviews
11 repeat clients
10 years of experience
Winnipeg, MB, R2V

“This was my first time using Rover and boarding my very anxious dog. I was nervous to leave him in a new environment, but he settled right in to Brock and Nicole’s home. They made sure he was comfortable the whole weekend and sent lots of photo updates! He had so much fun and we will definitely be booking with them again!!”

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Erin T.
Sitter Profile Image: Khushi K.
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Khushi K.
$50
total per night
5.0 out of 5 stars
• 4 reviews
2 repeat clients
2 years of experience
Winnipeg, MB, R3B

“My dog was much happier than when we have picked her up at a kennel in the past! It is my first time using Rover and I will definitely be booking again.”

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Rita B.
Sitter Profile Image: Hadas K.
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Hadas K.
$62
total per night
5.0 out of 5 stars
• 2 reviews
16 years of experience
Winnipeg, MB, R3N

“Hadas was wonderful with my senior shitzhu x. Very pleasant and accommodating. She kept me well informed and took pictures of my girl during her stay. I had a good experience and would use Hadas again.”

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D G.
Sitter Profile Image: Lise D.
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Lise D.
$56
total per night
5.0 out of 5 stars
• 16 reviews
2 repeat clients
18 years of experience
Winnipeg, MB, R2H

“Lise is very kind and Coco enjoys her very much. He is always updating and sending pictures of coco. for sure I will choose Lise again if we ever go on vacation again.”

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Ece P.
Sitter Profile Image: Kerry M.
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Kerry M.
$28
total per night
25 years of experience
Winnipeg, MB, R3J

About: Hi! I’m Kerry and I’d love to take care of your pet(s) while you’re away. Growing up around animals, caring for them has always been second nature to me. I've owned many cats over the years and one sweet pup who recently passed. I’ve been pet sitting for over 25 years...longer if you include sitting for friends and family. ​Whether it’s sticking to feeding routines, giving meds, light training, going on daily walks, or giving extra belly rubs, I treat every pet with the patience, care and attention they deserve. For your peace of mind, I’m also certified in Pet First Aid through the Canadian Red Cross. ​I know how important it is to feel confident about who is in your home. You can trust that I will treat your space with complete respect—keeping everything clean, secure, and tidy so you can return to a fresh house and happy pets after your trip. ​I look forward to meeting you and your furry family members! I currently work full time Monday to Friday in education. I get 1 to 2 days per week to work remote, which enables me to keep your pets company! I am able to care for dogs in my own home, provided you know they are able to get along with cats. Otherwise, I'm happy to sit in your home.

Sitter Profile Image: Catherine E.
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Catherine E.
$45
total per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
4 years of experience
Winnipeg, MB, R3B

“Catherine was very respectful and well mannered. She watched my cat for me and was very responsive on the app and sent photos and asked questions and took great concern in my cat’s comfort and safety. She washed the bowls and litter box I provided and was super nice. I will definitely book with her again.”

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Shyanne S.
Sitter Profile Image: Stacey S.
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Stacey S.
$62
total per night
5.0 out of 5 stars
• 19 reviews
4 repeat clients
13 years of experience
Lockport, MB, R1A

“Stacey did an amazing job looking after Ween. Her backyard is perfect for all sizes of dogs to run and play, and I loved all the videos that Stacey sent as well! I will be rebooking in the future for sure!”

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Ian P.
Sitter Profile Image: Carley W.
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Carley W.
$67
total per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
25 years of experience
Sunnyside, MB, R5R

“Aspen and Ember had a great stay! I was provided with updates and pictures thought out, which left my mind at ease. Carley made sure that the dogs were well acquainted during the meet and greet. Upon pick up, and arriving home they were calm and napped a lot after a playful weekend. Will definitely book again!”

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Kerstie K.
Sitter Profile Image: Shirlea F.
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Shirlea F.
$56
total per night
5.0 out of 5 stars
• 21 reviews
2 repeat clients
45 years of experience
Winnipeg, MB, R3T

“Shirlea is a caring, communicative, and very friendly person, and I'm incredibly grateful to her for taking care of my cat and dog while I was on vacation. I recommend Shirlea to anyone who needs reliable care for their pets. Thank you so much 😊”

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Marlena P.
Sitter Profile Image: Katrina & David B.
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Katrina & David B.
$33
total per night
18 years of experience
Winnipeg, MB, R2N

About: Both of us have grown up with family dogs and are hoping to add one of our own to our family when our schedule better allows for it! We love dog sitting for friends and family and decided it was time to help others out! We have watched big and small dogs for days up to weeks! Allow us to care for your pet, get our own puppy cuddles in and keep you at ease while you’re away! We currently both work full time but are home in the evenings and weekends. If needed, one of us can usually come home at lunch to let the dog out for a pee break and some cuddles! We have a large fenced in yard with lots of room to run and play! Crate during the day preferred as we are out of the house during weekdays!

Sitter Profile Image: Amanda g.
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Amanda g.
$50
total per night
5.0 out of 5 stars
• 15 reviews
4 repeat clients
20 years of experience
Winnipeg, MB, R2J

“Amanda went above and beyond with Kylo! He was so happy to hang out with her and her family and two other pets, a dog and a cat. She was so very attentive and made sure Kylo got his outdoor and play time. I would totally book with Amanda again. If you have any worries about pet care, she would be the one to calm all your worries!”

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Carolyn Z.
Sitter Profile Image: Aalisha P.
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Aalisha P.
$34
total per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
Winnipeg, MB, R2M

About: I grew up with birds and cats! My kitty is a year younger than me. I have 10+ years in experience with pet and babysitting x My availability is quite flexible! I prefer working in the afternoon or evening. However I don’t mind mornings! I am usually free on weekends x I have a 21 year old cat! She cannot eat dry food. Due to her age she most likely has dementia.. in order to make it easier for her we have two litterboxes x

Sitter Profile Image: Akosua A.
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Akosua A.
Star Sitter
$84
total per night
5.0 out of 5 stars
• 4 reviews
2 repeat clients
10 years of experience
Winnipeg, MB, R3T

“Thank you so much for taking care of my dog! I really appreciated the updates, photos, and the care you gave throughout the stay. You made the whole experience stress-free and I could tell my dog was comfortable and well looked after. I’d definitely book with you again and recommend you to others!”

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Khushi K.
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The median cost per night for pet 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 pet boarding

  1. 1. Search

    Browse profiles of sitters near you who offer pet 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 pet boarding - Headingley

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Sitters in Headingley average 6
repeat pet boarding clients

FAQs for Pet Boarding - Headingley

Frequently asked questions about Rover

The average cost of Pet 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 13 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.

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.

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.

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.

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