Pet Sitting Chestertown
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 80 pet parents in Chestertown have booked pet sitting
Chestertown, Find top rated pet sitting
“Elaine was amazing with my two dogs while I was out of town, she sent lots of photos and made sure they were well taken care of and having fun, it made my trip so much better with all of the updates!”
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’ve spent the last 15 years caring for animals and treating every pet like part of the family. I have hands-on experience with 3 cats, a lovable Frenchie Pug, and plenty of experience handling different pet personalities, routines, and energy levels. From daily walks and feeding schedules to playtime and cuddles, I make sure every pet feels safe, comfortable, and cared for while their owners are away. As a pet owner myself, I understand how important it is to have someone trustworthy and dependable caring for your pets. I focus on creating a calm, loving environment while keeping routines consistent so pets feel at ease. Whether your pet is energetic, shy, playful, or needs extra patience, I’m committed to giving them personalized care and attention every step of the way. I take care of my animals everyday I walk them and feed them and they use the restroom in our fenced in yard I give them lots of love as well I have a fenced in yard and 5 friendly animals 3 cats and 2 dogs who are docile and very friendly to any pet that comes in to my home
About: I have had dogs since I was in preschool. I started my understanding of them and other animals when I turned nine. Since then, I always have had my and other people’s pets interest at heart. Today, my dogs are ages eight and eleven and I am their most trusted person in the house. I’ve trained them both despite being in school and I take care of their hygiene. This includes brushing their fur, washing them, and cleaning their teeth. When I am not taken care of their hygiene, I make sure they have a daily playtime or cuddle session so they have some love everyday. I have a part time job that requires me to work on Friday evenings and every third Saturday morning and afternoon. Other than that I am very flexible on both weekdays and weekends. If I am unable to work, I will communicate immediately to the best of my ability. I make sure hazards are out of range and site of the animal in care. I don’t rush the bond, and take it to the pet’s pace for trust. At home, my dogs at senior dogs that I have trained since they were puppies and we have a lot of trust in each other and a great bond. I can’t perform service at my own house since I have a toddler sibling who my dogs have gotten used to but I do not want to stress anyone’s pets out. We also have family members who have allergies.
About: I will love and take care of your pets as if they were my own. I love to go out and play with pets I care for. I would dog sit when I was in high school for different families. Those families loved how attentive I was, and as a result they would refer me to their friends. I’m always available for you buddies! You and me both know that your pets are more than pets, theyre family. You don’t want just anyone taking care of family. I do currently work full time, however I have a job that is extremely flexible. I set my own hours, including when I am in my office. This pairs perfectly with animal care and house care because I can come and go as frequently as needed. Due to my open schedule I can be available for any needs your pets may have. I prefer to let the client tell me exactly what they want for their pet. I like to keep your life as simple as possible while giving you peace of mind by following any requests you have. If you need your animal crated, if you want them roaming, whatever is asked you can expect to be done.
About: I currently own a Pitbull she’s now 5 and my partners is 6 or so. I 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.
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.
“Sydney met with me and Jojo beforehand and then did a drop-in visit with Jojo. Jojo loved her visit. It was nice knowing I can count on Sydney while I am at work and I received a report card, pictures & a video! Thanks so much!”
About: I’ve taken care of dogs including raising 5 of my own for over 30 years. Happy to drop in or provide walks as needed. Look forward to hearing from you. I work from home every other week which enables me the flexibility to drop in and take your pup for a walk or feed and let them out. I’ve taken care of dogs including raising 5 of my own for over 30 years. Happy to drop in or provide walks as needed. Let me know how I can help
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: Animals have always been the center of my life, and caring for them is so much more than a job to me — it’s truly my passion. I currently have four dogs and five cats of my own, so I understand firsthand the love, attention, patience, and responsibility that go into providing excellent pet care every single day. My experience with animals goes far beyond personal pet ownership. I worked at a dog rescue for three years, where I gained hands-on experience caring for dogs of all ages, sizes, temperaments, and special needs. During that time, I also fostered 52 dogs, helping them transition into safe, loving homes. That experience taught me how to build trust with nervous pets, handle different personalities, and provide compassionate, individualized care. In addition, I have been working as a veterinary technician for the past two years, which has given me strong knowledge of animal health, behavior, safety, and overall well-being. I’m comfortable recognizing signs of stress or illness, administering attentive care, and making sure pets feel safe and supported. What sets me apart from other sitters is the genuine love and dedication I bring to every animal I meet. I treat every pet as if they were my own, and I’m committed to making sure they feel comfortable, happy, and loved while you’re away. Whether your pet is energetic, shy, senior, or needs a little extra patience, I have the experience and heart to provide exceptional care. Pet care is seamlessly integrated into my daily and weekly life. Each day, I set aside dedicated time for feeding, walking, playing, and providing companionship to ensure every pet receives consistent attention and care. Every pet receives the love, care, and attention they need to thrive, making their time with me a happy and fulfilling experience. When caring for pets, safety, trust, and a comfortable environment are my top priorities. In my home, I ensure a secure and pet-friendly space by removing hazards, providing comfortable bedding, and maintaining a clean environment. I follow the owner's instructions meticulously, maintaining their feeding schedule, exercise routine, and any specific care requirements. I build trust by being patient, gentle, and attentive, allowing pets to adjust at their own pace. Regular playtime, cuddles, and positive reinforcement help create a bond and alleviate any anxiety they may feel. In a client's home, I respect their space and maintain their pet's routine as closely as possible. I follow their instructions regarding feeding, walking, medication, and playtime. I ensure the home is secure, checking that doors and windows are properly closed and that there are no potential hazards. I communicate regularly with the owner, providing updates and photos to reassure them that their pet is in good hands. My goal is to provide a safe, trustworthy, and comfortable environment, whether in my home or theirs, so pets feel secure and loved in their owner's absence.
About: Although my family has never owned a dog, I have always loved taking care of my aunts, neighbors, and family friends dogs. I always make sure to pay attention to detail when watching a dog and meet each dogs needs whether that be a walk, playing with a toy, belly rubs, or even just relaxing. As a part-time graduate student at USM, I will have time during the day for a dog walk, or to check-in on your pup! I will be available on most weekends for house and dog sitting. I am available to come to your dog and stay with him/her so they do not have to move out of their comfortable environment and stay at a new space with new people.
About: I have pet sit for dogs, cats, horses, donkeys and chickens. I care for animals as if they are my own. I have worked at pet stores and started learning about dog training. I am working full time remotely so I have lots of time to help your pets with their needs! I am available most every day with notice! I will give your pets as much attention as they want and need. I will take them on walks, play with them, and protect them as if they are my own.
The median cost per visit for pet sitting in Chestertown is $20
Pet parents share their Rover experiences - Chestertown
Sabrina did a great job with our 22 year old cat, even spending extra time with her. Her many pics each day made leaving her alone for the week much more bearable. She paid close attention to our girl and informed us of anything that changed. We will definitely use her in the future.
Shaun was wonderful with our 22-year-old cat, Gizmo, over the Christmas holiday. He’s watched her several times now, and she consistently responds so well to him—something that means everything to us given her age. We have complete peace of mind when he’s caring for Gizmo and will absolutely continue booking with him. Highly recommend!
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 pets like family
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 near you
Select a filter and find qualifying Chestertown sitters!Sitters in Chestertown average 6 repeat pet sitting clients
FAQs for Drop-In Visits - Chestertown
Frequently asked questions about Rover
The average cost for Pet Sitting in Chestertown on Rover is $19.98 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 Pet 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 Pet Sitting. For more information on service fees, click here .
As of July 2026, there are 3,690 sitters on Rover offering Pet Sitting across Chestertown. 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 Chestertown 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.
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 Chestertown. On Rover:
- 94% 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.
A Meet & Greet is a short introductory meeting between you, your pet, 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.
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.
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