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
About: With seven years of experience, I provide reliable, loving care for pets, including feeding, walking, and administering medications! Your pets will be in good hands!! I am currently an undergraduate student at Tri-C. I schedule feeding, walking, and playtime to ensure pets’ needs are met consistently! Flexibility and time management allow me to provide loving, attentive care while balancing other responsibilities! I live in a neighborhood and my Golden Retriever is trained with an electric fence. I have worked with clients who have electric fences, a tie out in their yard, or have simply walk their pets to use the bathroom. I am open to anything!
“Dasha has been great with both of my dogs! Blue is a new puppy to us and certainly requires much more work, however Dasha was absolutely fantastic with him and he seemed very thrilled with having someone able to come and play with him while I was gone for the day!”
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 cared for animals of all kinds since I was 10 years old. Friends, neighbors, and family have always trusted me to walk, feed, bathe, and love their pets as if they were my own. I also have hands-on experience giving medications and vaccinations from my time working as a veterinary assistant. Over the years, I’ve cared for pets both inside and outside the home and have experience with boarding, dog walking, medication administration, and in-home visits for feeding and watering. Every animal I care for quickly becomes part of my extended family, and I truly enjoy every moment spent making them feel safe, loved, and spoiled. I currently work from home, giving me plenty of time to provide attention and companionship throughout the day. My schedule is flexible and is very convenient for those who may need a little extra attention. My fenced yard offers space to play, and my two friendly dogs are always ready to welcome a new friend. If needed, I can also easily crate your dog for comfort or routine.
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.
“Marti took great care of my two kitties! I would recommend her to anyone looking for a drop in sitter. She was very communicative and helpful. I came home to two happy cat brothers😻”

“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.”

“This was my first time having a sitter, and therefore my first time leaving my cat for a trip that was longer than a few days. Even though I was nervous, Ashley did a great job by ensuring me she was capable and excited to take care of my cat. While my cat doesn’t have any specific medical concerns, I do know she can be a bit finicky and I was worried about her not eating while I was away. Not only did my cat love Ashley and continued eating, I got updates even though I wasn’t able to view them for a while, due to international travel that I could look back at and know that she was well taken care of. My home and my cat were safe while I was on my vacation and I could be stress-free. If I ever need to travel again, I will definitely be booking with her in the future.”

About: Hi! I’m Maria, and caring for animals isn’t just something I do, it’s something I’ve dedicated years of my life to. I have over 10 years of hands on experience working with dogs of all ages, sizes, breeds, and personalities. From energetic puppies to senior dogs who need a slower pace, I understand that every pet deserves care that’s tailored specifically to them. My partner and I work together as a team, which means your pets receive twice the attention, care, and reliability. Having two experienced animal lovers allows us to be flexible with scheduling and provide consistent, dependable care for your pets, whether you’re away for the day or an extended vacation. I offer: • Dog Walking • Drop-In Visits • House Sitting • Overnight Boarding • Puppy Care • Senior Dog Care • Medication Administration (if needed) • Lots of playtime, cuddles, enrichment, and exercise! I’ve cared for everything from tiny toy breeds to giant breeds, including dogs with anxiety, high energy, special routines, and unique personalities. I also have experience with cats and other household pets, so if your family includes more than just dogs, they’re in great hands too. When your pet stays with us or we care for them in your home, they’re treated like family. We stick to their normal routine as closely as possible because we know consistency helps pets feel safe and comfortable. Whether that means long walks, endless games of fetch, quiet cuddle time, or simply keeping them company, we adjust our care to what makes your pet happiest. As pet owners ourselves, we understand how difficult it can be to trust someone with a member of your family. That’s why communication is one of our top priorities. You’ll receive regular updates, photos, and messages so you can enjoy your time away knowing your pet is happy, loved, and well cared for. Our goal isn’t just to watch your pet. We want to become someone both you and your furry family member can trust for years to come. We’d love the opportunity to meet you and provide the same love, patience, and attention we give our own pets every single day. We can’t wait to meet your best friend! 🐾 One of us works full time, however the other stays at home and focuses on animals and etc. We’re always able to be flexible and accommodate everyone’s needs We always make sure to meet prior to bookings and if needed or wanted to I do like to send pictures and videos of your fur babies while in my care. I know everyone misses their little babies.
About: With over two decades of hands-on animal experience, I bring a deep understanding of pet behavior, health needs, and the importance of maintaining their routine while you're away. My experience includes: Behavioral observation: Skilled at reading animal body language and recognizing signs of stress, illness, or discomfort Medication administration: Comfortable giving pills, liquid medications, and following specific health protocols Routine maintenance: Experienced in maintaining feeding schedules, exercise routines, and providing the consistency pets need Emergency awareness: Trained to recognize when situations require immediate veterinary attention Gentle handling: Patient approach with anxious, elderly, or special-needs pets What sets me apart is my genuine passion for animal welfare combined with practical experience in rehabilitation and long-term care. I understand that every pet is an individual with unique needs, and I'm committed to providing the same level of attention and care I'd want for my own pets. I work from home and welcome the chance to get out of my home office and play with your adorable floofballs. Weekdays during work hours make up the bulk of my availability, but I can be flexible with evenings and weekends. I prioritize creating a safe, low-stress environment, whether caring for pets in my home or others. In client homes: I maintain pets' established routines to minimize anxiety and provide consistency Secure all doors, windows, and gates to prevent escapes Follow all specific instructions regarding food, medications, and behavioral needs Provide regular updates with photos and messages to keep owners informed Respect the home environment and leave it exactly as I found it Safety protocols: Always have emergency veterinary contact information readily available Monitor pets closely for any changes in behavior, appetite, or health Ensure all pets are properly secured during transitions (leashes, carriers, etc.) My 23 years of experience have taught me that prevention is key. I'm constantly aware of potential risks and take proactive steps to ensure every pet feels safe and comfortable. Trust is earned through consistent, reliable care and clear communication with pet parents.
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.
About: I have had cats dogs and other pets ever since I was little I can’t live my life without them now I want to make a little bit of money doing what I love to help supplement my income. I have plenty of time to care for animals other than and as well as my own. Being with animals is the one thing that truly makes me happy.But please only send pets that have been spayed or neutered. Please no pet that will pee all over my house. I have a fenced in backyard two cats and one dog. I have a cat tower and a large cage to crate your pets or my own if needed. But my dog loves a good play date
About: I have been taking care of dogs since I was about 6. I’ve grown up with both small and large dogs, specifically Golden Retrievers, Labs, and Boston Terriers. I have cared for my dogs as well as other other people’s. Hi! I’m Sydney! I am a law student at Case Western and am living in Little Italy. I love going on walks and would love to walk dogs as part of my daily routine. My weekends are relatively quiet, making me a good fit for in home dog care! I will care for pets according to instructions, including frequent potty breaks, walks, and play time as needed. I am able to provide medicine as well as specific food requests if necessary.
About: I’ve been around all animals my whole life, My friends and family have always called me an animal whisperer because I’ve never met an animal that didn’t like me. I’m skilled in reading body language and respecting animals so they feel comfortable with me. I’m a customer service manager full time all week but will be available all weekend at all hours of the day and night so you can be free on weekends. I’m respectful of home I come to and if needed to come to mine I have a service animal that is good with all dogs but can be put away if needed.

About: I am a lifelong animal lover and I share a special connection with them. I have an Australian Shepherd, Kodi Wilde and a kitty called Audrey. I have over 15 years experience as a professional petsitter. I volunteer at a local animal shelter to walk dogs and give them love and playtime. I believe pets are family members and I will show yours the same love and care I show mine. I will protect your pets and keep them happy. I love to take them for walks or jogs. I am happy to watch them in your home as well. In addition to keeping your furry friends happy and healthy, I can keep you updated with photos and videos so you can relax during your time away. Call or text to set up your complementary meet and greet. My schedule is very flexible. I am happy to accommodate your pets scheduled and keep you updated. My goal is to keep your pet happy and safe while you’re away. We have a large fenced in back yard and I’m also happy to take your dog on hikes! I typical separate pets at feeding time.
About: I’ve taken care of both cats and dogs of every kind since I have been 10. I love taking long, walks, playing, and hope to build a connection with both you and your pet. I currently work full time- I have flexibility for constant care Friday-Monday (I work remotely on Mondays and am off Fridays). Depending on location, I am able to come during my lunch to let the dogs out (a typical work day is 6-7 hours for me). I have flexibility to leave and come back during the day, or stay the entire day and spend the night! I can take your dogs on long walks, and am comfortable cleaning up messes if needed. I am also comfortable taking your pet to appointments, as well as co sleeping if they are anxious!
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.
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: I will make sure to give all of my attention and love towards your dogs and keep them good company. I am very responsible with taking care of dogs and will make sure they get the exercise they need if that is what I am asked to do. I will even just watch them while you are gone and keep them company. I will do anything they need and make sure they are okay. I can't wait to meet all of the wonderful furry friends I will get to meet. This is my full time job at the moment so I have a lot of availability to care for your dogs and cats and dedicate my time. I care for pets and others homes. I have lots of experience going and doing pet care and other people’s homes. I’m very respectful of others houses.
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.



