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.
About: I’ve provided care for animals since I was a young child. Successfully completed a basic dog training course at Alaska SPCA in 2016. My skill ranges from walks to grooming, I’ve got you covered! Currently, I’m working full-time with free availability Sunday through Tuesday! I will require at least a three day notice before the date of booking. Please message me for any questions you may have! I have a balcony and plenty of space for your fur baby to lounge and play. Currently my roommate is an agreeable cat. Chai is pleasant and tolerable to other cats and small dogs.
About: I’ve taken care of my own dogs growing up as well as friends dogs over the years. I walk / hike a lot and love being outside, if your dogs are comfortable at parks I’d love to take them out ! My friends and family have relied on me a lot for holidays and special occasions or to just check in while they work to take them on a walk or for some pets / play time. I always send photos for updates on how the fur babies are doing during our visits :) I’m very reliable and have a flexible work schedule that I know 2-3 weeks in advance. I’m always looking forward to meeting new people and their animals ! I do also work another job, but I know my schedule 2-3 weeks in advance and have breaks to come and check on pets also! I don’t care for any other animals at my home besides my own cats! But I always come and meet everyone beforehand and get a run down of everything I’ll need to know for the time I’m watching them!
About: I love the clients I get to work with as a pet sitter. I love providing stress free and reliable pet care for people when they need the help. It's a big deal to let someone into your home and trust them with the care of your pets. I understand the responsibility and don't take it lightly. I am experienced with puppies and dogs, cats and farm animals, special needs, reactive and senior dogs. I treat others' pets as if they were my own. It brings me a lot of joy to make your pet feel loved, happy and safe. I'm comfortable crating, walking, giving medicine and other special needs. There's nothing I won't do for your pet - its a very important member of your family! I can provide any additional references upon request! Pet sitting fits into my routine perfectly because I work remotely, so I have the flexibility to be with your animal/s as much or as little as you prefer! I care for my clients pets based on their requests, preferences and routines. I am comfortable walking, crating, giving commands, and following each person's instructions for how they want their animals to be cared for.
About: I stand out because of my years of experience, genuine love for being with dogs, and a track record of trust with numerous satisfied clients who have relied on my services! Despite my work commitments, I am dedicated to incorporating pet care into my daily routine. I prioritize morning and evening sessions for feeding, walks, and quality time with your pet. Additionally, I ensure that your pet has a comfortable environment during the day. Communication is key, and I'll keep you informed with updates, so you can have peace of mind while you're at work. In both my home and yours, I prioritize a safe and comfortable environment for your pets. In my home, I create a pet-friendly space with designated areas for play, rest, and meals. Daily walks and engaging activities are part of the routine. For in-home services, I adapt to your pet's familiar surroundings, maintaining their routine while providing personalized care. Regular communication and updates ensure you have peace of mind, knowing your pet is well-cared for in either setting.
About: Your pet will be treated like family! 🐾❤️ I’m a caring, patient, and dependable pet sitter who understands how important it is to feel comfortable leaving your pets with someone you trust. I take the time to learn each pet’s personality, routine, feeding schedule, and individual needs. Whether your dog loves long walks and playtime or your cat prefers a quiet space and lots of cuddles, I’ll make sure they receive plenty of attention and care while you’re away. I’ll follow your instructions carefully and keep you updated with photos and messages so you can have peace of mind. 🐶🐱❤️ I’m reliable and will make sure your pets get the care, attention, and routine they’re used to. I’m happy to communicate with you about the best times for visits and make sure everything is taken care of while you’re away. 🐾❤️ I have pets of my own, so I understand how important it is to feel comfortable leaving your pet with someone you trust. I’m gentle, patient, and respectful of each pet’s space and personality. I’ll follow your instructions carefully and make sure your pet is safe, comfortable, and well cared for in their home. 🐾😊
“I needed help last minute. Savannah was more than willing to help and responded quickly. She took tons of pics of my boy and adjusted to our needs. I will be contacting her again.”

About: When it’s time to go outside it’s time. Clean up areas where the pet(s) have pooped @. Please make sure they are trained with handling strangers. Thank you ! Currently, I am currently working part-time after almost a 9 months of unemployment. I have time for pet care services. Just a American putting effort in the American Dream for myself. Since I will take them out to poop, pee & food I’m going to be diligent on that note ! Close & lock doors is a must !
About: I grew up in a house with dogs, and have been caring for them my entire life! I’ve had dogs as large as Great Danes or as small as chihuahuas. I’m comfortable caring for all sizes and ages of dogs, and can assist with supplemental training with simple commands such as learning to sit. I’m also happy to assist with any additional care needs such as light grooming, outdoor playtime, or administering oral medication. Monday-Friday I am available until noon for any morning pet care needs. I can assist on weekends or evenings after 9pm as needed- just ask and I am sure we can work something out! Since I am experienced with caring for pets of all shapes and sizes, I am always able to take a calm and unique approach to make sure your pets are comfortable and safe. I pay close attention to body language, and integrate your pet’s personality into my care to make sure they feel respected and stay safe. I love animals, so I always care for them with enthusiasm and make sure they know how much they are loved!
About: Hi my name is aaziya and I have over 10 years of pet care experience and I am very flexible. Whether your fur baby is reactive, special needs, or you have specific instructions on how you want them cared for, I do it all! My schedule is very open due to the fact that I just left a pet grooming job where I didn’t feel very much comfortable and couldn’t fit into my day to day life Since I don’t have anything other than getting my son to and from daycare that needs my attention, your pet will have all of my undivided attention to care for all their needs! I also have a very large yard for them to either burn energy or just relax in the sun.
About: I’ve grown up with both dogs and cats my entire life, and caring for animals has always been something I genuinely love. I’ve pet sat for neighbors, friends, and family, caring for pets with different personalities, routines, and needs. Whether it’s walks, feeding, playtime, cuddles, or simply keeping them company, I always make sure they feel safe, comfortable, and loved while you’re away. What sets me apart is that I’m also a registered nurse. My career has made me compassionate, dependable, detail-oriented, and attentive to changes in behavior or health. I have a natural instinct for noticing when something doesn’t seem quite right, and I always prioritize safety and communication. I understand that pets are family, and I promise to treat yours with the same love, patience, and care I would give my own. I currently work part time, which gives me a flexible schedule and plenty of time to dedicate to the pets I care for. Whether it’s going on walks, playing, keeping them active, sticking to their routine, or simply giving them companionship throughout the day, I’m happy to provide the care they need. I genuinely enjoy spending time with animals and will make sure your pet feels safe, loved, and well cared for while you’re away. Since I live in the city, I don’t have a fenced yard, but that doesn’t stop my dog from getting plenty of exercise and attention! I have one dog of my own and also frequently care for my neighbor’s dog. We go on regular walks throughout the day, visit nearby grassy areas for bathroom breaks, and enjoy trips to the park just up the street for extra exercise and playtime. I also have a crate available if your dog is crate trained or if you’d like them crated for rest, bedtime, or while I’m briefly away. When caring for pets in a client’s home, I always follow their routine as closely as possible. I make sure they’re fed on schedule, have fresh water, get plenty of exercise, playtime, bathroom breaks, and, of course, lots of love and attention. My goal is to help every pet feel comfortable, safe, and happy while their family is away.
About: Dogs have always been a key component of my life. Recently, I simultaneously cared for a trio of Pit Bulls over the past decade. I have a large 'fenced in' back yard (40' x 220') and a walk-in dog shower in my basement if needed. I am a semi-retired school teacher. After a year of travel (Key West & Cape Cod), I returned to Cleveland and I am excited to care for dogs once again, which allows me to work on fixing up my home and yard. My home and yard is your dog's home and yard. If you leave you dog with me for the day, I will be present during the entire time. For extended stays, I do not leave for more than a period of three hours. My home and yard are all-natural, chemical free. I do not use treated mulch or any fertilizers. The dogs I have been watching all enjoy exploring the many aromas of the back yard.
About: I’ve had pets my entire life and taken care of them by myself as well as helping friends and family care for theirs when they were away. My schedule is pretty open but changes day to day. I’m happy to try to work around your schedule! If I happen to be booked, I hope you keep me in mind next time! I am unable to have pets in my apartment unfortunately because my cat does not like other animals. I am only able to care for pets inside your home or outside.
“Jenna was absolutely amazing with our dogs! She was so kind and patient with them and took awesome care of them while we were out of town. Our dogs tend to be a little nervous but she was so patient and kind with them and they warmed up so quick to her! She is so reliable and it was such a relief to know that my pups were in good hands. Thank you Jenna!! You’re the best!”

About: I grew up around dogs and have a heart for them. I love them and will take great care of them like I do my own fur baby. They are our family forever!!! ❤️❤️❤️ I am teacher, so I am currently on summer break from school. This allows me to have some extra time to walk your dog, check in and let my dog make some new friends with your fur baby! Our fur baby has a crate and a warm, loving home where she is spoiled rotten! I would do the same for your pup to make sure they receive the best care possible.
“You will never book another sitter again after meeting Bryan! He loves and understands cats so truly and provides the best, most thoughtful updates. My cat is my baby and my best friend and I have never felt more secure with her in someone’s care!! He took care of absolutely everything and ensured he knew all about her quirks and personality and play habits and veterinary information just in case. She seems so happy and well taken care of! I assure you, your cat will love Bryan.”

About: I’ve always loved being around animals and have experience helping care for pets for friends and family. I’m reliable, attentive, and quick to learn each pet’s unique needs and personality. I’m committed to following all instructions closely and making sure your pet feels safe, comfortable, and cared for. I treat every pet like my own and always aim to create a positive, stress-free experience for both pets and their owners. I currently have tons of availability due to just leaving my job and doing this full time as I search for something else I have plenty of time to care for your pet! While caring for your pet in your home I will give them much playtime time, love and attention! I will treat your fur baby as my own
About: Growing up I’ve always loved animals, As a child I would rescue stray dogs and provide food, care and shelter. I helped many pets get back to there homes also. My dream was to become a veterinarian, though I took a different route my love for animals never left and I still operate in a field of care. The Different pets I had where birds , fish , turtles, rabbits , dogs and cats. I’ve always prided myself on knowing the intricacies about the different breeds of animals and what makes them special or unique and what they require to be healthy and happy. Though I’ve had many breeds of animals I know I still have much to learn but one day I aspire to open a shelter or nonprofit organization for pets in need of a loving home. Trusting your animal with me I can Guarantee there safety and protection but also ensure that in my home will be equally as loved. I’m familiar with grooming techniques, administering shots for puppy’s and medicines a dog may require. I can also make sure that anything you may be teaching your pet will be carried out while in my care or any schedule you may have your dog on will be implemented also. I’m currently working part time so I’ll have plenty of time to play with your pups and walk then 4/5 times daily. Two long walks and two short walks and extra if the weather is nice or we are outside taking adventures. I prefer evening drop offs and pickups. I care for pets often. This is something I genuinely love to do. I like to follow the instructions owner give when taking care of their pets
About: Hello! For my whole life, I’ve been taking care of several family dogs and cats, foster dogs and cats, and for the past 3 years I have a cat of my own! I foster cats, kittens, dogs, and cats whenever I can, and sometimes take care of pets of my friends and family members! I am experienced with taking care of bigger dogs and dogs that are very high energy and excitable as well. I also have experience with giving medicine to dogs and cats. Let me know if you have any questions or concerns, I look forward to hearing from you! I work part time and only have online classes, so my schedule is very flexible. I can always rearrange my schedule to take care of animals if needed. I have a huge fenced yarded for cats and dogs to run around and play. I also have plenty of rooms in my house for animals to stay.
About: I spent most of my childhood at neighbors’ houses helping walk, play with, and care for their pets. I always knew I wanted one of my own, and when I finally got my dog, people constantly complimented his obedience and sweet, playful personality. I’m a dependable, active, and patient pet sitter who treats every animal like my own. I don’t just stop in and leave, but I make sure pets get exercise, attention, and real care. I understand how much trust it takes to leave your animals with someone, and I take that responsibility very seriously. I typically work from home and live near parks, so I look forward to taking your pet(s) on walks, snuggling, and playing with them. I have a fenced in yard, but I always supervise my pets when they are outside. I keep my pets occupied constantly with frozen Kong toys, frozen lick mats, interactive toys, single ingredient treats, single ingredient bully sticks, etc.
The median cost per visit for dog sitting in Chesterland is $20
Dog 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 dog sitting

1. Search
Browse profiles of sitters near you who offer dog 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 dog sitting - Chesterland
Select a filter and find qualifying sitters offering dog sitting.Sitters in Chesterland average 6 repeat dog sitting clients
FAQs for Dog Sitting - Chesterland
Frequently asked questions about Rover
The average cost of Dog Sitting in Chesterland is $16 per visit as of October 2026. Most bookings cost between $11 and $28 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 October 2026, there are 2,138 sitters on Rover offering Dog 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.
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 .
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 , 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 .
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:
- 90% of sitters can help with special care needs
- 94% 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 , 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.




