Cat Sitting in Chestertown
Book a cat sitter to stop by your home to feed and play with your cat.

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Top rated Chestertown cat sitters

“Marissa IS THE BEST CAT SITTER OF ALL TIME. 10/10 WILL BOOK AGAIN! 5/5 Stars! 2 thumbs up! 100% positive experience! She’s a cat whisperer! I love her! She’s extremely helpful and communicative!! Very accommodating to my needs and my cats needs!”


“Great experience with Shaun. Despite short notice just before Christmas, he was available and was great about meeting our cat before we booked him. Would definitely use him again.”


“Absolutely phenomenal! She was detailed Available and went the extra mile with taking care of my fur babies. She was very easy to communicate with. Easy going and helped me feel comfortable with my animals and home. We will definitely use her again! Book with Payton you won’t be disappointed!”


“Zelle was tremendous! When we first met she put me at ease right away, so friendly and asking such good questions. She really wanted to understand our dogs differing needs. During our absence, she checked in at our agreed upon times and sent lovely pictures at each check-in. It was such a comfort to know my fur babies were cared for so lovingly. Will not hesitate to call on her again.”



About: I've been around animals as long as I can remember. I currently have a puppy named Star and three cats Persephone (Purrsi), Odin and Loki. I foster for the local QA shelter and have worked in a vets office for a short time. I am lucky enough to work out of my house or remote so I am available seven days a week with enough notice. I can come to you or provide care in my house. I live in an end unit Duplex. I have a fenced in yard complete with a puppy pool and beds for lounging. I can provide care in my home or come to yours. Following directions and care requests provided is not a problem.

About: I've had the privilege to care for many types of animals through my life. Caring for animals is my passion in life, and I will happily care for yours like they are my own. My private sitting is more cost effective than boarding you pets. If you have multiple pets I am willing to negotiate my fees to help you afford quality care for your pets. It causes them less stress being in their own home. They won't be around pets they don't know. There will be no chance of them catching an animal illness or be injured by another pet. I will only be caring for your pets so they will have all of my attention and affection the whole time you are away not divided among however many pets are being boarded during that time. I can also stay with them overnight so if anything happens they will not have to wait until someone arrives in the morning to check on them. I will keep your pets on whatever schedule you would like. Depending on your needs I will happily take them for walks, play with them, love them, and am comfortable giving meds. I have taken care of pets for friends, family, neighbors, and clients. I also have experience with many types of animals, but will follow the instructions you give as you know what your pet needs more than anyone else. I will send photos and updates however often you would like to let you know how they are doing. Unlike leaving them at a boarding facility your pets will be the only ones I am caring for and will receive my full attention. I will also always have my phone on if you need to reach me about anything. I currently live with my husband, 4 dogs, 1 bird, and several hermit crabs. I work primarily on my computer and am home most of the day. My husband can care for our pets when I am not home so I can focus fully on caring for yours. If you need someone who can stay home all day with your pets while you're away, I can easily work remotely from your home. I may need to occasionally run errands, but unless discussed before hand, I will not be gone for more than 2 hours. I am currently unable to stay away from my home for more than 2 days as I have family obligations that are preventing me from staying longer. I should be able to return to longer overnight stays in the summer. I work remotely from home. This leaves me in a great position to work remotely from your home while caring for your pets. I also make my own schedule so if you just need me to stop by: to feed, play with, pet, walk, or just be there so they aren't alone all day, I will happily do that too. I will always listen to what you tell me your pet needs. For example if you have a fenced yard that you would like me to walk them in on a leash, I will do just that. I won't make assumptions about what is safe for your pet. You know them best and I will care for them in whatever way you want me to. Their health and safety is always my top priority.

About: I’ve been dog walking and sitting for neighbors since I was 12 years old. I’ve dog sat multiple types of dogs. I’ve done dog walking, check-in & potty break visits, and I’ve stayed at a clients home for long periods of time (5+ days) to be with their pups. I’ve also been tasked with administering insulin shots to dogs before. And I have a lot of experience with dogs that have anxiety, whether with new people, thunderstorms, or anything else, as I have one myself and a long remaining client of mine does as well. I’ve always loved dogs, having grown up having 2 smaller dogs myself. I am hoping to do pet sitting as a new permanent business, so I will have nothing but time to look after your pets! I will schedule out days and time periods based on client necessity and to provide the optimal care for your pets. Because I have two dogs myself, one of which has severe people and other animal anxiety, which for the safety of your pets and mine means I am unable to bring any pets into my home as of current. However, I’ve stayed at the homes of clients before to be with their pups while they’re away. I feed them every morning and night or make sure the food bowl is full depending on how the client feeds their dogs. I give them any medicine or joint tablets that they need to be well. I let them out multiple times a day whenever they need it. And I try to play with and pet them as much as I can while I’m there so they don’t miss their humans too much. I will even take them on a walk if allowed.

About: I have grown up around cats, dogs, and other pets and love to take care of them. I've been house and pet sitting for almost my entire life. I am an animal lover and will always give extra attention to your pets. I am up for any task and promise to give full care and love to your pet! I love being outside and playing so this is perfect for high energy dogs. I also enjoy lounging around and hanging with pets, perfect for lower energy dogs. Either way, animals intrigue me in every aspect and I love working with them. I am available at 3:00pm on weekdays and all day on weekends. I am available after 3:30pm on weekdays and all day on most weekends. I am happy to do overnights and/or routine drop-ins. Most weeks I have multiple dog walks. I typically do overnights in your own home. I am able to do drop-ins of any length when it fits my schedule. Feel free to reach out as I am flexible.

About: Skillful pet caregiver for your fur baby. I’ve taken care of pets and have had a love for animals my entire life. Friends and family know that they can rely on me to love, socialize, walk, feed and bathe their pets. I work a very flexible schedule which allows me to have control of my schedule therefore I’m able to be super flexible with the hours that I choose to care for your pet(s). Pets are under my supervision at all times. If needed I’m also able to crate your pet as well. When going on walks all pets will be securely leashed.

About: I have loved animals since I was a little girl! I have many years of experience with dogs, cats and even small animals like hamsters, turtles and fish. I want to be there for you, and your furbaby so you can fully relax on that vacation you have been looking forward too! I am currently employee at Washington College with a pretty loose schedule! Being able to choose my hours and be able to work around yours is 100% a possibility that sets me apart! I live in an apartment with a fenced in backyard. I live in downtown chestertown which is open to all different types of walking opportunities and is a short walk to many fields at the college!

About: I currently own a Pitbull she’s now 3 and have had 3 other dogs in the past. I love all dogs big or small and am happy to give them the attention they need. If you have other pets in your home that is okay I have no allergies and am good with most other pets. Each pet is unique and may need extra care and I am more than okay with that. I am a nice, kind, and caring person and love animals with all my heart. I am great with specific schedules, being punctual, and love giving pets attention. I am here to make your life easier and help take care of your best friend(s). I work full time 8-5pm and I am free Saturdays. I always will be transparent about my schedule to be sure everything goes per expectation. I’m very respectful of your home and space. I want you to be able to go about your life and not be worried about your pets or anything on my end.

“Madison was awesome! I was in a pinch and she stepped with very short notice and took great care of koda! I was very pleased and will definitely be using Madison again in the future”


About: I have been born and raised to take care of any type of family member from the small lizard to largest dog to feathered friends and horses. I love all animals and I have family members of my own. Plus I have a little helper who isn't scared of anything and loves to help her momma as much as she can. I'm will to do what ever it takes to make sure everyone is a happy camper and provide the best care I can to keep your mind at ease knowing you family is in good hands. Feel free to ask me anything and if you have any special requests let me know I will do what I can to make it happen. I'll treat your kids as if they were my own. I'm currently employed part-time but I'm looking to get out of the retail business and starting my own pet sitting business where I can enjoy doing what I love. I currently live in a small apartment, so it ideal that I travel back and forth from my house to clients home. I have fur babies and a family of my own, hopefully when I get a home of my own I could introduce the doggy daycare and pet sitting at my home.

About: I have a veterinary assistant certification and 2 years of experience in the field. Animals are my passion and I love seeing them happy & healthy! My schedule is fully open. I have the time & flexibility and would love to care for your furry family member! Please feel free to message me with any requests! I have a small dog and two cats so I’m accustomed to their daily needs and care. I will keep all dogs on a leash at all times outside to insure their safety. Only exception being if the client has a fenced in yard. No human food or possible choking hazards will be laying around for pets to get into.
Loving cat sitters in your neighborhood
Search Results


Marissa F.Star Sitter

“Marissa IS THE BEST CAT SITTER OF ALL TIME. 10/10 WILL BOOK AGAIN! 5/5 Stars! 2 thumbs up! 100% positive experience! She’s a cat whisperer! I love her! She’s extremely helpful and communicative!! Very accommodating to my needs and my cats needs!”


Lisa M.

“Lisa did a great job taking care of our 4 high-maintenance cats!”


Maura M.

“Thank you Maura? We are pleased with the care you provided for Molly and Olive. Knowing you were there gave us peace of mind and enabled us to enjoy our visit with our Grandson.”


Shaun C.

“Great experience with Shaun. Despite short notice just before Christmas, he was available and was great about meeting our cat before we booked him. Would definitely use him again.”




Carrie D.

“Carrie took great care of our cats!”


Payton W.

“Absolutely phenomenal! She was detailed Available and went the extra mile with taking care of my fur babies. She was very easy to communicate with. Easy going and helped me feel comfortable with my animals and home. We will definitely use her again! Book with Payton you won’t be disappointed!”


Tori V.

“Tori does a great job of taking care of our shy kitty Winnie!”


Divya J.

“Divya is awesome you can tell she really cares about the animals and she is really good at communication I would definitely book with her again”


Zelie K.

“Zelle was tremendous! When we first met she put me at ease right away, so friendly and asking such good questions. She really wanted to understand our dogs differing needs. During our absence, she checked in at our agreed upon times and sent lovely pictures at each check-in. It was such a comfort to know my fur babies were cared for so lovingly. Will not hesitate to call on her again.”




Elizabeth W.
“Ashley W is the best. I have 2 active large dogs, Maisie (6 years old) and Petey (7 years old), who she has taken care of since they were puppies. She has been there for learning manners, leash training, zoomies, park play time, and overnight stays. My dogs absolutely love her and look forward to more playtime with her. She is always on time, communicates with me about all the details, and makes sure my babies are well cared for while I'm gone. I never worry about my pups while they are with her. I highly recommend Ashley W.”


Caroline B.

“Caroline is a star! I cannot say enough about her. Trustworthy, caring, professional and so loving to our furry babies. Highly recommend her!”


Sabrina G.
“Sabrina is a very conscientious dog owner. They have 3 dogs of their own that are all rescues. She has fostered problem dogs for a local rescue and taught them to behave so that they were adoptable.”


Ashley C.
About: I’ve been dog walking and sitting for neighbors since I was 12 years old. I’ve dog sat multiple types of dogs. I’ve done dog walking, check-in & potty break visits, and I’ve stayed at a clients home for long periods of time (5+ days) to be with their pups. I’ve also been tasked with administering insulin shots to dogs before. And I have a lot of experience with dogs that have anxiety, whether with new people, thunderstorms, or anything else, as I have one myself and a long remaining client of mine does as well. I’ve always loved dogs, having grown up having 2 smaller dogs myself. I am hoping to do pet sitting as a new permanent business, so I will have nothing but time to look after your pets! I will schedule out days and time periods based on client necessity and to provide the optimal care for your pets. Because I have two dogs myself, one of which has severe people and other animal anxiety, which for the safety of your pets and mine means I am unable to bring any pets into my home as of current. However, I’ve stayed at the homes of clients before to be with their pups while they’re away. I feed them every morning and night or make sure the food bowl is full depending on how the client feeds their dogs. I give them any medicine or joint tablets that they need to be well. I let them out multiple times a day whenever they need it. And I try to play with and pet them as much as I can while I’m there so they don’t miss their humans too much. I will even take them on a walk if allowed.


Haley Z.
“She has a soft spot for all living things especially dogs. Being athletic as she is I know dogs would appreciate and benefit from Interacting with her on a daily basis.”


Kashya J.
About: Skillful pet caregiver for your fur baby. I’ve taken care of pets and have had a love for animals my entire life. Friends and family know that they can rely on me to love, socialize, walk, feed and bathe their pets. I work a very flexible schedule which allows me to have control of my schedule therefore I’m able to be super flexible with the hours that I choose to care for your pet(s). Pets are under my supervision at all times. If needed I’m also able to crate your pet as well. When going on walks all pets will be securely leashed.


Gillian H.
“Gillian is an amazing and caring pet care giver. When ever she looks over my dog she is nothing but the best, and my dog just loves her”


Madison M.
About: I currently own a Pitbull she’s now 3 and have had 3 other dogs in the past. I love all dogs big or small and am happy to give them the attention they need. If you have other pets in your home that is okay I have no allergies and am good with most other pets. Each pet is unique and may need extra care and I am more than okay with that. I am a nice, kind, and caring person and love animals with all my heart. I am great with specific schedules, being punctual, and love giving pets attention. I am here to make your life easier and help take care of your best friend(s). I work full time 8-5pm and I am free Saturdays. I always will be transparent about my schedule to be sure everything goes per expectation. I’m very respectful of your home and space. I want you to be able to go about your life and not be worried about your pets or anything on my end.


Madison P.

“Madison was awesome! I was in a pinch and she stepped with very short notice and took great care of koda! I was very pleased and will definitely be using Madison again in the future”


Cynthia R.
About: I have been born and raised to take care of any type of family member from the small lizard to largest dog to feathered friends and horses. I love all animals and I have family members of my own. Plus I have a little helper who isn't scared of anything and loves to help her momma as much as she can. I'm will to do what ever it takes to make sure everyone is a happy camper and provide the best care I can to keep your mind at ease knowing you family is in good hands. Feel free to ask me anything and if you have any special requests let me know I will do what I can to make it happen. I'll treat your kids as if they were my own. I'm currently employed part-time but I'm looking to get out of the retail business and starting my own pet sitting business where I can enjoy doing what I love. I currently live in a small apartment, so it ideal that I travel back and forth from my house to clients home. I have fur babies and a family of my own, hopefully when I get a home of my own I could introduce the doggy daycare and pet sitting at my home.


Hannah B.
About: I have a veterinary assistant certification and 2 years of experience in the field. Animals are my passion and I love seeing them happy & healthy! My schedule is fully open. I have the time & flexibility and would love to care for your furry family member! Please feel free to message me with any requests! I have a small dog and two cats so I’m accustomed to their daily needs and care. I will keep all dogs on a leash at all times outside to insure their safety. Only exception being if the client has a fenced in yard. No human food or possible choking hazards will be laying around for pets to get into.
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1. Search
Read verified reviews by cat parents like you and choose a sitter who’s a great match for you and your cat2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your cat while you’re away3. Book & Pay
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Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your cat sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total cat fanatics. You can get in touch with us anytime.
Cat Sitting FAQs
Frequently asked questions about Rover
Cat sitters on Rover are free to set their rates. The median cost to hire a cat sitter in Chestertown on Rover as of Aug 2025 was about $22 per night, after factoring in Rover’s service fees. A cat sitter’s rate may also change as you customize your booking to fit your and your cat’s needs.
As of Aug 2025, there are 189 cat sitters in Chestertown. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect cat sitter near you. As a reminder, cat sitters joining Rover must pass a background check for you and your cat’s safety.
Rover makes it easy to reach out to multiple cat sitters about your booking. Typically, 84% of Chestertown cat sitters respond in under an hour.
Cat sitters in Chestertown have an average of 16 years of experience. Cat sitters with repeat customers have an average of 7 repeat clients. Experience can vary from cat sitter to cat sitter, but you can view reviews, years of experience, and number of repeat clients when you compare cat sitters in Chestertown.
Do you simply need someone to stop by and play, feed, and scoop? Chestertown cat sitters are happy to take care of your cat while you’re at work, on vacation, or unavailable for the day, even if all you need is a quick drop-in! Your cat sitter will stop by to feed, play with, and snuggle your cat as many times a day as you like. And the best part? Your cat gets to stay on their home turf.
There are 189 cat sitters in Chestertown on Rover, so you’re sure to find the perfect match for your cat! In Chestertown, 98% of cat sitters offer daily exercise, 98% offer medication administration, and 93% have experience with senior cats and cats with special needs. We know each cat is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect cat sitter near you. As a reminder, cat sitters joining Rover must pass a background check for you and your cat’s safety.
Yes! Cat sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your cat sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your cat sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your cat is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your cat sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your cat sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your cat sitter’s cancellation policy.
