Pet Boarding Headingley

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

End Date
Search

Over 115
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: Bibiana R.
Verified Background Check
Bibiana R.
Star Sitter
$46
total per night
5.0 out of 5 stars
43 reviews
14 repeat clients
16 years of experience
Winnipeg, MB, R3Y

Bibiana is an expert sitter. Cocoa tends to be anxious and wary in unfamiliar situations, but Cocoa spent a very comfortable week with Bibiana. Thank you.

Profile image
Seungki K.
Sitter Profile Image: Birch S.
Verified Background Check
Birch S.
$50
total per night
5.0 out of 5 stars
5 reviews
2 repeat clients
18 years of experience
Stonewall, MB, R0C

It was a fantastic stay, with walks and photos. She also very thoughtfully made Sophie a bandana. Our dog would definitely enjoy staying again!

Profile image
Lindsay N.
Sitter Profile Image: Sunisha M.
Verified Background Check
Sunisha M.
$56
total per night
5.0 out of 5 stars
20 reviews
5 repeat clients
10 years of experience
Winnipeg, MB, R3Y

Sunisha did a wonderful job in taking care of Rocky . Rocky needed special care because of his old age. Sunisha kept Rocky very comfortable during his stay & took care of giving him medication daily. Thanks Sunisha & family for being a wonderful host for Rocky.

Profile image
Jatinder S.
Sitter Profile Image: Julius & Glenda R.
Verified Background Check
Julius & Glenda R.
$33
total per night
5.0 out of 5 stars
9 reviews
35 years of experience
Winnipeg, MB, R2P

Our first time using Rover, and Julius and Glenda truly exceeded our expectations! They treated Bella like their own, giving her so much love, attention, and care. It gave us such peace of mind during our vacation knowing she was in such good hands. We couldn’t have asked for a better experience, highly recommend their service to anyone looking for trustworthy and caring sitters!

Profile image
Monette R.
Sitter Profile Image: Jaspreet & Carlos K.
Verified Enhanced Background Check
Jaspreet & Carlos K.
$45
total per night
4.4 out of 5 stars
7 reviews
3 repeat clients
3 years of experience
Winnipeg, MB, R3C

Highly Recommend

Profile image
Justice A.
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
32 reviews
13 repeat clients
50 years of experience
Winnipeg, MB, R3J

Mary Anne was absolutely amazing with Ollie. We felt very good knowing our “baby” was in her hands. She sent us pictures and comments about Ollie’s activities daily. When we left Ollie, he was a bit scared of the new space, and didn’t want to eat much. Mary Anne was so accommodating when we asked her to boil ann egg for him. With that she won him for the rest of the stay 😄. She even spoiled him, letting him sleep with her! We are planning our next trip and we already booked her again!

Profile image
Ana P.
Sitter Profile Image: Titiksha T.
Verified Enhanced Background Check
Titiksha T.
Star Sitter
$28
total per night
5.0 out of 5 stars
77 reviews
23 repeat clients
10 years of experience
Winnipeg, MB, R3C

Titiksha was amazing, I got updates every day and she kept my dog very active and socialized him a bunch. He felt right at home and she treated him like family! I have found my new regular sitter!

Profile image
Alannah Z.
Sitter Profile Image: Ranchelle O.
Verified Background Check
Ranchelle O.
Star Sitter
$50
total per night
4.9 out of 5 stars
70 reviews
26 repeat clients
29 years of experience
Winnipeg, MB, R2R

Our corgi seemed to have had a great time. Ranchelle was a great communicator, was accommodating to our schedule and appreciated all the videos and pics sent.

Profile image
Julie H.
Sitter Profile Image: Karen R.
Verified Background Check
Karen R.
Star Sitter
$23
total per night
5.0 out of 5 stars
46 reviews
16 repeat clients
8 years of experience
Winnipeg, MB, R3J

Karen was amazing!! This was my first time using Rover so I had a few questions she happily answered. She was easily available for dropping off and picking up my cat and the transition was very smooth. She sent pictures of my cat immediately so I knew she was in good hands. She continued to send at least one picture or video a day but usually sent a few throughout the day. I will definitely have Karen watch my cat again and recommend her to anyone looking for a cat sitter!

Profile image
Savannah S.
Sitter Profile Image: Pamela H.
Verified Background Check
Pamela H.
Star Sitter
$45
total per night
4.9 out of 5 stars
49 reviews
14 repeat clients
14 years of experience
Winnipeg, MB, R2H

Pamela did so well with Mikai! She was very communicative and accommodating, it was greatly appreciated! Will definitely have Mikai stay with her again! Thanks again Pamela! ☺️☺️

Profile image
Haziel F.
Sitter Profile Image: Stephanie O.
Verified Background Check
Stephanie O.
$45
total per night
4.8 out of 5 stars
132 reviews
61 repeat clients
25 years of experience
Winnipeg, MB, R3J

Stephanie was amazing with my pups! Great communication and she dealt really well with how clingy my little Ollie is. 10/10 would book with her again!

Profile image
Calypso M.
Sitter Profile Image: Lovepreet B.
Verified Background Check
Lovepreet B.
$34
total per night
5.0 out of 5 stars
2 reviews
1 repeat client
5 years of experience
Winnipeg, MB, R2G

Our Bella had a great stay, was well looked after and sitter very responsive.

Profile image
Abigail C.
Sitter Profile Image: Ariana R.
Verified Background Check
Ariana R.
Star Sitter
$45
total per night
5.0 out of 5 stars
37 reviews
11 repeat clients
5 years of experience
Winnipeg, MB, R3T

Ariana was so sweet with Pinot! She sent regular check-ups with pictures and made sure Pinot was well-fed during his stay. She has a lovely puppy that was also so gentle and loving with our dog Pinot. The two of them seemed to get along great! Thank you so much Ariana! Pinot will definitely be back :)

Profile image
Mélanie M.
Sitter Profile Image: Polina B.
Verified Enhanced Background Check
Polina B.
Star Sitter
$50
total per night
5.0 out of 5 stars
50 reviews
18 repeat clients
12 years of experience
Winnipeg, MB, R3C

My cat stayed with Polina for 12 days and he was comfortable and happy throughout. She sent pictures and videos of him daily. She played with him and brushed him and snuggled with him. He came home happy and well cared for. She had all his things (litter box, bowls, etc) clean and ready to go. I would definitely leave him with her again. 😻

Profile image
Meghan R.
Sitter Profile Image: Tanya G.
Verified Background Check
Tanya G.
$47
total per night
5.0 out of 5 stars
2 reviews
15 years of experience
Winnipeg, MB, R3N

Tanya communicated very promptly both pre-booking and during. She sent photos and updates throughout the week which were much appreciated. Would recommend!

Profile image
Karen C.
Sitter Profile Image: Camila C.
Verified Background Check
Camila C.
$56
total per night
5.0 out of 5 stars
10 reviews
1 repeat client
10 years of experience
Winnipeg, MB, R3N

Camila was amazing. She gave updates daily on how Zeus was doing. She went above and beyond for my little guy, who can be a handful. He can be anxious when he’s not home/with me and she made sure he was as comfortable as she could!

Profile image
Carina H.
Sitter Profile Image: Richard & Melissa M.
Verified Background Check
Richard & Melissa M.
$45
total per night
5.0 out of 5 stars
6 reviews
1 repeat client
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: Erin & Mason L.
Erin & Mason L.
Star Sitter
$76
total per night
5.0 out of 5 stars
11 reviews
4 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.

Profile image
Jennifer E.
Sitter Profile Image: yudong j.
Verified Background Check
yudong j.
$50
total per night
5.0 out of 5 stars
3 reviews
10 years of experience
Winnipeg, MB, R3T

Yudong took excellent care of my dog, Junior! He responded to my messages right away, kept me updated throughout the stay, and sent lots of pictures, which gave me great peace of mind. It was clear that Junior had a wonderful time and was well cared for. I would definitely book with Yudong again whenever I need a sitter. Highly recommend!

Profile image
Vivek B.
Sitter Profile Image: Katie J.
Verified Background Check
Katie J.
$54
total per night
5.0 out of 5 stars
27 reviews
3 repeat clients
30 years of experience
Winnipeg, MB, R3T

Katie was simply amazing. I knew my dog was in good hands as soon as I met her. She was loving and extremely caring. I got regular updates about my pet

Profile image
Adarsh B.
1 / 1
View more sitters

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.

Meet local sitters who will treat your pets like family

  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

Sitters in Headingley average 6
repeat pet boarding clients

FAQs for Boarding - Headingley

Frequently asked questions about Rover

The average cost for Pet Boarding in Headingley on Rover is $49.02 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 Pet 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 Pet Boarding. For more information on service fees, click here .

As of July 2026, there are 208 sitters on Rover offering Pet Boarding across Headingley. Enter your postal code to see which available sitters are closest to your home.

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.

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 pet, 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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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