Pet Sitting Chesterland
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 21 pet parents in Chesterland have booked pet sitting
Chesterland, Find top rated pet sitting
“Courtney was the first sitter I ever hired for my cat, and I couldn't have been more pleased. My cat showed great comfort with her, allowing me to fully enjoy my trip. Will definitely be booking again in the future!”
About: Hello! My name is Shawntel and I have been an animal lover for as long as I can remember. Growing up, my family had 2 dogs and 4 cats. Now I have three dogs that I couldn't imagine my life without them, with two of them being rescues. When I’m booked for house/dog sitting, my dad gets to stay and spend time with his grand-pups (: One is a German Shepard mix, another one is a Pitbull, Husky, Lab mix, and my newest addition is a golden doodle! The German Shepard is a senior so I am used to making accommodations for animals as well as giving mediations. It doesn't matter if they are young or old, big or small, boy or girl-- I love them all. I am currently a first grade teacher in Lake County which I recently took time away from dog sitting to focus on my new position. But now I’m back!! So I am available before and after the school day during the week for your animals and pretty free on the weekends. I am usually pretty flexible so if you need anything special for your animal, just let me know! I also dedicate my summers and school breaks to house/dog sitting! I truly believe that a well taken care of animal is a happy one, and who doesn't want their fur baby happy?! I look forward to meeting you and your sweet animal(s)!! I am currently a first grade teacher in Lake County which I recently took time away from dog sitting to focus on my new position. But now I’m back!! So I am available before and after the school day during the week for your animals and pretty free on the weekends. I am usually pretty flexible so if you need anything special for your animal, just let me know! I also dedicate my summers and school breaks to watching animals! I truly believe that a well taken care of animal is a happy one, and who doesn't want their fur baby happy?! I look forward to meeting you and your sweet animal(s)!! I know animals feel most comfortable in their own home so I mainly watch animals in the clients home. I do my best to give them the love and attention you give them while you are away.
About: We have two dogs, Duke and Dixie, who have completely different personalities. I love them both! We have always had dogs and it's so comforting and fun. My schedule is super flexible because because I have online school and home with access to a car. I could also do my school from your home. I have plenty of time to play and care for your cats or dogs! I have a flexible schedule for drop-in visits for your pets. I will follow all of your instructions when caring for your pet/s. I will communicate any questions or concerns that I have during my visit. My top priority is making sure your pet is properly taken care of and happy!
“Randy was terrific! He was very responsive, dependable and took great care of our two cats. He played with them, fed them and cleaned their litter box. He went above and beyond!”
About: Dogs have been in my life since I was young! I have my own, and love to help out friends, neighbors, and family in need! I work part time, hybrid locally. Very available through out week except on Tuesdays. I’m flexible and usually can adjust with enough communication ahead of time! My fur baby sleeps in bed with me or in his own crate as needed. Typically he comes to work with me when I go into my office as well.
About: I have been a pet owner and a pet sitter for over a decade. I grew up with pugs and now have a very happy, sweet, old boxer/pittie mix named Lou. From 2016-2017, I worked at a dog daycare in New York City, walking pets to and from home and daycare, and managing rooms of dogs of all sizes while they played, ate meals, and were boarded. I am comfortable walking and caring for dogs of all sizes. I love going on long walks as well. I have reliable transportation and am lucky to have a very flexible schedule. I am currently between full-time work as I recently moved back to Cleveland after 7 years in Miami, Florida, so I am very available for your pet care and pet walking needs. I am very comfortable with dogs of all sizes and other pets including hamsters, cats, and birds. I am also comfortable administering medicine as needed, am comfortable crating dogs, and can works with whatever needs your pet may have.
About: I just moved back to Ohio and I have had pets my whole life and lost my baby a bit ago. I know how they are family and deserve all the love. My dog was older and had a lot of health issues so I am familiar with different medication that may be needed. I’m currently in grad school for nurse anesthesia and study most days from home. I have a pretty open schedule except Thursday and Friday morning-afternoon but can be available early in the am or that evening. Happy to answer any questions. Anytime except Thursday and Friday 6am-4pm (I have clinical at the VA for grad school) I have online lectures so I can have open availability during the rest of the week and weekends. I can discuss as well. I would prefer to watch your loved one at your home or do day sitting/walks. My current family dog is very timid and a rescue and is scared of literally everything so I don’t want to stress him out
“Anthony has been checking on my dog Cooper while I’m at work for about two weeks. He is great and very knowledgeable with dogs. He makes sure Cooper lets out some energy and takes him on walks. Highly recommend his business.”
“This is the second time we've booked with Makenna, and I'm yet again a happy customer! She's done a house sitting and drop in visit with fantastic through updates. I feel relieved she's taking such great care of my dog and cat.”
“Ben did a stand-out job when it came to drop-in visits for our dog while we were out of town. He reviewed our request with such detail that he was able to spot a mistake I made with the booking & ultimately ensure that our dog got the best care under his watch. He offered to meet our pup before we left town & they hit it off right away! The picture updates Ben sent with each drop-in was proof that our dog was being treated well & was happy to see Ben each time he stopped by. We are so appreciative of Ben & the care he provided our dog while we were out of town.”
“Jenna is an amazing pet sitter. We needed someone who could come spend some time with our new puppy and she has done a great job. She always provides feedback and lets us know how her visit went along with a cute photo. We couldn’t have found a better sitter. Thank you Jenna!”
About: Hi my name is Yocheved, but a lot of people call me Yo, or Ava. I am an only parent to a wonderful, active middle schooler. We have a happy home full of love and laughter, and 2 kitties. After 14 magical years together, we lost our dog to old age, a couple years back. I miss the feel of having a dog around, but I know in my heart of hearts we are all a little older, and a little busier, and our home cannot house a new permanent four-legged resident. But I do not accept the lack of dogs in our lives! I said yes to dog sitting lately, and I have made so many new friends since. Hanging out with your dogs or cats when you're unable to be there- it's become a thing I look forward to in my home. I love walking the neighborhood or doing drop-ins to feed cats. Let me help you! I'm currently WFH part time, and tend to end my days on the early side, for parenting purposes. Because of this I'm pretty flexible and available throughout the week. I tend to all pets, like I would for my own. I cared for my dog through cancer, twice- so I'm pretty familiar with medicine, senior care, and all the extra effort needed for older or sick animlas. I love to walk, burn off energy, and snuggle. Happy to do light grooming (brushing), and send photos and videos throughout our time together!
“Octavia was amazing with our dogs! She sent photos and kept me updated every time she visited. We are always nervous to leave our dogs when going out of town but Octavia always made me feel that they were being taking care of with tons of love. I strongly recommend her!!”
“Carla is awesome, coming to the rescue with a last-minute cat visit when I had to leave town suddenly and giving them and my house the best care and me, peace of mind. I genuinely appreciate her flexibility and sweetness, and we would welcome her back anytime for future travels!”
About: I have a dog of my own (pappion) and have had him since I was about 9 years old! He is the dearest thing to me and I love him with my whole heart! Which I will be sure to give your pet all the love and attention he/she deserves!! I also used to have a siemeze kitten who sadly died of cancer. But I loved her to the moon and back and continue to! I am currently still looking for a job so right now, I'm all yours! Willing to chat and come up with ideas! I'm very flexible and easy going! Sadly, I am not planning on bringing your pets to my house. Due to liability and things. But I will gladly come over to your house and do what you need done!
About: I have 3 dogs that I live with in different sizes. They all have different personalities and needs. I am comfortable with all kinds of dogs, big or small. I’m currently working part time so I have a lot of free time to walk and take care of your pets! Looking forward to it! I have a big backyard with lots of space and lots of treats and toys for the puppies. They will have the best time ever.
The median cost per visit for pet sitting in Chesterland is CA$20
Pet parents share their Rover experiences - Chesterland
She stopped by for a check in on my dogs while we were out of town. My dogs absolutely loved her, she was very responsive on needs that needed to happen for my dogs and even sent pictures of them! Would definitely recommend her to anyone needing their dogs taken care of!
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 sitting
1. Search
Browse profiles of sitters near you who offer pet sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for pet sitting - Chesterland
Select a filter and find qualifying sitters offering pet sitting.Sitters in Chesterland average 6 repeat pet sitting clients
FAQs for Pet Sitting - Chesterland
Frequently asked questions about Rover
The average cost of Pet Sitting in Chesterland is $16 per visit as of November 2026. Most bookings cost between $11 and $35 per visit. 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.
As of November 2026, there are 2,211 sitters on Rover offering Pet Sitting across Chesterland. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
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.
Yes, you can find sitters who have experience with handling special pet needs in Chesterland. On Rover:
- 89% of sitters can help with special care needs
- 94% 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.
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.
sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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