Dog Sitting Chesterland
Book a Chesterland dog sitter to watch your dog in your sitter’s home or yours.

Over 15 pet parents in Chesterland have booked dog sitting
Chesterland, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Brandon was great! I knew he was going to be great fit since the meet and greet. Our dog Benji loves him. Milo will take a bit of time but I'm sure over the next few visits Brandon will win him over too.”

“Catherine took good care of my bunnies while I was on a trip. She put good attention to their care and made sure they were eating well and comfortable!! She also communicated very clearly and promptly which made me feel at ease that they were in good hands. Thank you Catherine!!”

About: While growing up, I fed, watered, played with, and walked our family friends. I even picked up poop! As an adult, I've done it all, from cleaning major messes to administering meds. I love canines and felines of all varieties, from the smallest to the largest! I am available to care for your pet(s) throughout the business day. Although I am also doing some volunteer work, I keep a regular schedule. I will care for your pets according to your express instructions. They will be treated as my own with as much love and concern as I can provide.
About: Dog owner for 20+ years. Homeschool mom with all day availability except for on Fridays 9am-2pm. Do not have a pet now and are missing the experience having a dog. Looking to give the experience to love and support to my kids without owning a dog. Perfect for dog walking, playing, and poop picking upping while you are away at work or trips. I currently am only working 9am-2pm on Fridays and am available to care for your pet(s) before or after and every other day of week including weekends! I do not have a fully fenced in yard BUT I do have three fences. I like to be super active and playful with the dogs. I will walk them multiple times a day. I am also willing to take them to the dog park (only 15 minutes away from my house) I will can crate train or let them free roam my house. I treat these pups like they are my own! And I will follow any rules you wish for me to keep up!
“Respectful and Professional, got along great with my precious creature. Followed instructions perfectly, and reached out when needed. Could stand to be more assertive w/ dogs sometimes, but still a great sitter. 10/10 would book again :)”

“Kristine did a great job looking after our dogs. She gave us very detailed updates and the cutest pictures. They had a blast with her and we would definitely have her watch them again!”
“Nicole did a great job dropping in to visit my puppy, Luna, during the day while I was at work. Nicole did drop-in visits for several months, and she was always on time and was super easy to communicate with, even if I had to cancel last minute. I highly recommend Nicole for drop-in visits!”


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.
“Molly was amazing! Upon doing meet and greet you could tell she was professional and reliable. She was quick to communicate and great with sending updates. You could tell she really cares about your pets. Will definitely book with Molly again!”

About: I have owned 3 dogs and a cat in my life. My ex-fiancée and I owned a Siamese cat that we adopted from the OKC Animal Shelter. We previously fostered two kittens. I'm reliable, accountable, and punctual! And above all, I am CPR certified for both humans and animals. You can count on me! I'm currently working full-time and do Rover on the side, but I will absolutely try to work around your needs! I am open to any and all animals! Let me know what availability you have and we can work with that! I do have a cat crate and some cat treats and toys. I do also have dog treats and chew toys. I am very gentle and know how to approach animals in a way that does not make me appear threatening and will earn their trust.
About: I’ve been sitting for friends and family since 2018 and I’ve steadily been gaining clients ever since ! My job is to take the best care of your pets that I possibly can ! This is my career, taking care of and loving pets…people say “do what you love and you’ll never work a day in your life.” It’s so very true! I do walks and sits and I’m currently working on getting my grooming license ! I try to emulate your schedule to the best of my ability and treat your pet as my own. When I had my dog he was the light of my life and center of my universe. I know how important pets are, they are family. I will treat your baby with the utmost respect and love, while they are in my care !
“Kacey took excellent care of my two cats when I was gone and went above and beyond what I would expect from a sitter. I would definitely hire again in the future and highly recommend her to anyone looking for a reliable, caring cat sitter.”


About: Since I was 11 years old putting dog walking flyers on my neighbors porches, I have always had a passion for taking care of animals. I still have people contacting me to cat or dog sit for them, and they love to recommend me to their friends. I love animals, and I know how to handle them safely and responsibly. From working with horses to dolphins, I have been around many different animals. I have owned reptiles and guinea pigs as well as dogs and cats, I have been working with and riding horses since 2018, and every summer since around 2020 I have gone to the Florida Keys and learned about training dolphins, I have aged out of that program now. I also volunteered at an animal shelter when I was younger. I am looking for a job to use my skills with animals. I work at a veterinary practice for a large animal veterinarian currently on Wednesdays and Fridays. I am looking for another job that I can work on Mondays, Tuesdays, and Thursdays. I can also do weekends if you are looking for someone who will stop by and take care of your animal for 30 minutes to an hour, but I like to have time on my weekends to spend with my loved ones, so the activities that take longer I would like the save for weekdays. I promise to love and take care of your animal as if it is my own until their favorite person comes back! I have my own reliable transportation, I can take your dog to a dog park if it is dog friendly, or I have a lot of land at my house. I also could take it to any walking paths. I know how to handle animals of all temperaments, and I am a good communicator and will keep you updated. I would love the opportunity to take care of your animal! I work at a veterinary practice part time on Wednesdays and Fridays and I generally start early in the morning around 7, and it’s a 40 minute drive. My hours can vary but I’m usually done sometime before 4pm. I can do drop by visits on those days early in the morning and after 5pm. On Mondays, Tuesdays, and Thursdays, I can do dog walking, dog sitting, or doggy day care at my house! Anything that generally takes a decent amount of time I can do on those days. On the weekends, I can do house visits for 30 minutes to an hour, but I would like to keep my weekends open as much as possible to spend time with friends and family and go to the barn. I have my own cat as well as 4 other cats, an english bulldog, and a french bulldog owned by my boyfriend’s family that I live with. I generally feed and take care of my cats and the other cats, but I used to pet sit for them and took care of their dogs as well. As far as caring for animals in my own home, I live on 8 acres of land, some of which is a field blocked off by tree line that would be a perfect place to play. I also have a fenced in concrete and grass area for the dogs to use the restroom. I have crates in my house where I can separate dogs if needed. I also know of lots of places to walk dogs, and live by a couple of dog parks. As for care in a clients home, I have lots of experience. I can do litter boxes, feed and water animals, and give enrichment and treats if requested by the owner. I can also let dogs outside on leash, or in a fenced in backyard. I’d rather be safe than sorry, so I avoid taking a dog off leash if they do not have a fenced in or secluded area. I can take them on walks around your neighborhood as well. I am also willing to take care of exotic animals or livestock, as I have plenty of background in that as well.
“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.”

About: Dogs have always been a big part of my life. When a couple of years ago we lost our senior family dog, I started volunteering with a local rescue and have fostered 20+ puppies over the past few years. Fostering has given me experience with everything from energetic, playful pups to post-surgery care—things like baths, basic grooming, medications (even injections), vet pickups, and lots of patience and love. I also help neighbors with dog walking and pet sitting, so I’m used to different personalities and routines. I truly just love being around dogs—and getting outside for walks is a bonus for me too! I’m available for afternoon and evening walks or check-ins during the week. On weekends, I have much more flexibility and I am available throughout the day for walks, check-ins, or multiple visits if needed. I’m also happy to stick to your dogs’s usual routine to keep them comfortable and happy. Your pet’s safety and comfort are my top priorities. During walks and check-ins, I follow your instructions closely, keep dogs secure on leash, and make sure they get the right balance of exercise, attention, and care. I’m attentive, reliable, and treat every pet like my own.
The median cost per visit for dog sitting in Chesterland is $20
Dog parents share their Rover experiences - Chesterland
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 dogs like family

1. Search
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Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests near you
Select a filter and find qualifying Chesterland sitters!Sitters in Chesterland average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Chesterland
Frequently asked questions about Rover
The average cost for Dog Sitting in Chesterland on Rover is $16.05 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting 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 Dog Sitting. For more information on service fees, click here .
As of July 2026, there are 2,185 sitters on Rover offering Dog Sitting across Chesterland. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Chesterland stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Chesterland choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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.
A Meet & Greet is a short introductory meeting between you, your dog, 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.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Chesterland with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Chesterland. On Rover:
- 96% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 96% 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.
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.








