Pet Boarding Headingley

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

Pick-Up
Search

Over 120
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: Sunisha M.
Verified Background Check
Sunisha M.
$56
total per night
5.0 out of 5 stars
22 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: Kyla W.
Verified Background Check
Kyla W.
Star Sitter
$39
total per night
5.0 out of 5 stars
4 reviews
3 repeat clients
16 years of experience
Winnipeg, MB, R3J

Kyla was so pleasant and easy to communicate with. My pup Ivy loved her yard and playing with Floyd. Great experience and hope this is one of a few visits for Ivy.

Profile image
Delilah B.
Sitter Profile Image: Julius & Glenda R.
Verified Background Check
Julius & Glenda R.
$33
total per night
5.0 out of 5 stars
14 reviews
1 repeat client
35 years of experience
Winnipeg, MB, R2P

My pup was super well taken care of and loved like he was their own, and Zeus is in love with them. Definitely recommend this petsitter as a first choice. I will be leaving my fur baby with them again!

Profile image
Denise S.
Sitter Profile Image: Gaia G.
Verified Enhanced Background Check
Gaia G.
$34
total per night
5.0 out of 5 stars
11 reviews
1 repeat client
5 years of experience
Winnipeg, MB, R2M

Took good care of our dog Mocha! She also took excellent photos! No qualms the first time we did a meet and greet first. Totally trustable. For sure we will leave our dog Mocha with her again.

Profile image
Marifel L.
Sitter Profile Image: Stephanie O.
Verified Background Check
Stephanie O.
$43
total per night
4.8 out of 5 stars
135 reviews
63 repeat clients
25 years of experience
Winnipeg, MB, R3J

Stephanie was absolutely wonderful with my 5 month old puppy. It was my first time leaving Winnie, but Stephanie did a great job of treating her like family for the week. I was always sent photos and videos with daily updates. Stephanie was a great person for me to trust with Winnie.

Profile image
Erica K.
Sitter Profile Image: Karen R.
Verified Background Check
Karen R.
$23
total per night
5.0 out of 5 stars
47 reviews
17 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: Titiksha T.
Verified Enhanced Background Check
Titiksha T.
Star Sitter
$28
total per night
5.0 out of 5 stars
88 reviews
24 repeat clients
10 years of experience
Winnipeg, MB, R3C

Mr. Anderson and Sir Norman clearly had a better vacation than we did. They were spoiled, loved and cared for like royalty (which, according to them, is simply the minimum standard).We came home to two cats who barely seemed to notice we'd been gone...which is probably the biggest compliment of all! Wouldn't hesitate to book with again. Thank you Titiksha for taking such amazing care of our boys!

Profile image
Annette P.
Sitter Profile Image: Kendall M.
Verified Background Check
Kendall M.
$56
total per night
5.0 out of 5 stars
8 reviews
3 repeat clients
14 years of experience
Winnipeg, MB, R3T

Leaving your dog with someone can be nerve-wracking, but after Kendall and her family watched Stanley, every bit of anxiety I had completely disappeared. I felt so blessed knowing Stanley was in such a beautiful, loving home where he was truly treated like part of their own family. Kendall is incredible with young pups and all types of dogs, making sure every pet feels completely comfortable and cherished. They went so far above and beyond—taking Stanley to the lake, introducing him to her extended family, and letting him play to his heart's content with the other dogs. Stanley was in absolute heaven! The moment I knew just how much love he felt was when Kendall shared that Stanley slept right on her pillow, exactly like he does with me at home. On top of all that, Kendall kept me connected with daily texts, photos, and video updates; my heart was filled with so much love and gratitude every time a message popped up. Kendall and her family are remarkable, and I cannot recommend her highly enough to anyone looking for extraordinary care for their dog.

Profile image
John D.
Sitter Profile Image: Anna S.
Verified Background Check
Anna S.
Star Sitter
$62
total per night
5.0 out of 5 stars
85 reviews
31 repeat clients
8 years of experience
Winnipeg, MB, R2L

I highly recommend Anna as a dog sitter! She's kind, caring, and friendly. Anna provided regular updates with pictures, and our dog, Poppy, felt at home with her. It was great to know that Poppy was in good hands and well looked after. The fenced yard was a plus, and it was comforting that Poppy was with a family that was home throughout the day. We felt at ease leaving Poppy with Anna and her family, and we're grateful for their excellent care.

Profile image
Kelli S.
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
45 reviews
14 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.
Sitter Profile Image: Polina B.
Verified Enhanced Background Check
Polina B.
Star Sitter
$50
total per night
5.0 out of 5 stars
54 reviews
19 repeat clients
12 years of experience
Winnipeg, MB, R3C

Polina is absolutely amazing! We’ve trusted her with our cat Candy multiple times, and every experience has been absolutely top-notch. She is caring, reliable, and always makes us feel confident that Candy is in great hands. We highly recommend Polina and will definitely be coming back to her with Candy again! 😊

Profile image
Alexandra H.
Sitter Profile Image: Lovepreet B.
Verified Background Check
Lovepreet B.
Star Sitter
$34
total per night
5.0 out of 5 stars
7 reviews
2 repeat clients
5 years of experience
Winnipeg, MB, R2G

Lovepreet was a wonderful host for Ozzy. She took good care of Ozzy. She connected with us throughout Ozzy’s stay by sending us the pictures and updates. Highly recommending her.

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

Ranchelle and Joshua were amazing with my fur baby, I was kept updated everyday it was my first time leaving him for more then 3 days so I was very anxious but that was instantly all gone once I saw all the pictures and videos sent to me of Morty having the time of his life,Having Yuri and Luna to play with made him very happy I could tell. he even came back to me with a new pep in his step, he doesn’t pull me as much and walks along side me instead of dragging me half way down the street. I will book with them Again forsure ❤️❤️

Profile image
Tionne S.
Sitter Profile Image: Lin L.
Verified Background Check
Lin L.
Star Sitter
$50
total per night
5.0 out of 5 stars
15 reviews
3 repeat clients
17 years of experience
St.Germain South, MB, R5A

Lin took care of my darling really well. She didn’t get fat so I assumed a lot of walking and playing was done. She sent me pictures all the time and I was really very happy my dog is happy with her. There were no issues and she made sure to ask questions. I got my darling back healthy and safe.

Profile image
Marie B.
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

Oleksandra and Liudmila took such great care of Atlas for the 3 weeks that we were away. We’re so happy we found such a great family to watch our dog while we’re away. Thank you!

Profile image
Kimmy L.
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

Amazing Sitters!

Profile image
Justice A.
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: Arissa R.
Verified Background Check
Arissa R.
Star Sitter
$62
total per night
5.0 out of 5 stars
34 reviews
8 repeat clients
16 years of experience
Winnipeg, MB, R3L

Another happy sleepover with Arissa. Our pup loves her snuggle time and always comes home happy and healthy. Will book again in the near future!

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

Pamela gave our 13-year-old dog Maisie the best care we could have asked for. She is a warm, caring dog lover who understands what they need. Maisie had a great time going on walks and meeting other dogs under the calm watchful eye of Pamela. I highly recommend her.

Profile image
John B.
Sitter Profile Image: Kuljit & Titiksha S.
Verified Enhanced Background Check
Kuljit & Titiksha S.
$27
total per night
5.0 out of 5 stars
23 reviews
7 repeat clients
10 years of experience
Winnipeg, MB, R3C

Aelin normally will be scared the first few days in a new space but from the photos i got she seemed completely comfortable right away clearly had a great time!! Kuljit and Titiksha were wonderful!!

Profile image
cameron l.
1 / 1
View more

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

Popular requests for pet boarding - Headingley

Select a filter and find qualifying sitters offering pet boarding.

Sitters in Headingley average 6
repeat pet boarding clients

FAQs for Pet Boarding - Headingley

Frequently asked questions about Rover

The average cost for Pet Boarding in Headingley on Rover is $48.77 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 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 September 2026, there are 206 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