House Sitting in Chestertown

“Ashley is a wonderful dog and house sitter! She took great care of Sadie for a week while we were out of town. She did everything I requested and was always very kind and courteous. The house looked exactly how we left it. Not a thing out of place. She is very trustworthy and highly dependable. I would recommend her to anyone!”

Anne H.

About: I am insured through Pet Sitters Associates. I have 2 pups Chip & Lucy ages 11 & 8 that I have raised from puppies. Many of my friends have dogs and they frequently come over. I also enjoy riding horses when I can. I have experience with working with anxious dogs & dogs in shelters also (as a volunteer). I love to take dogs for walks, to play with them & give them attention. I limit the amount of dogs I take at any given time so each pup gets lots of individual attention. You can see some of the dogs I have walked/played with in my profile pictures. I’m frequently in the Chestertown area and am more than happy to help with your pet sitting needs. I offer drop off and pick up of your pups for boarding. I am available weekday mornings 6-11 /evenings 5-10 and all day on the weekend. I can do boarding in my home after a meet and greet. I have a fenced yard and 2 friendly dogs. I can also kennel your dog if needed. Meet and greet of dogs would be needed before any overnight stays with us.

“Marissa took care of both dogs and the house while I had to travel for a week. I appreciate her care and thoughtfulness. I didn't worry at all.”

Janice C.

About: I’ve grown up with dogs all my life and have spent a lot of time dog sitting for friends and family. Whether it’s playtime, walks, or just providing loving companionship, I treat every dog like there my own. I’ve had experience with all types of dogs and would love to help out!! I'm currently a college student and will be home for the summer with a very flexible schedule. I have plenty of free time and can usually help out whenever needed. Since my summer plans are very flexible, I’m able to adjust my schedule to fit your pet’s needs. In my home, dogs are part of the family. We stick to a consistent routine. Walks three times a day, feeding in the morning and evening, and lots of quality time when we're home, which is most of the time. Play is a big part of our day, especially with toy-loving dogs! I provide a safe, loving, and attentive environment, and I extend that same care to every dog I look after.

“This was our first time using Savannah. Our pup seemed happy in all the pics she sent! It’s nice to have someone close by that can check in on Ruger when my husband and I have long days away! We will definitely be utilizing her again soon!”

Jessica K.

About: I’ve been caring for animals since I was 18, and for me this is more than a job, it’s truly a part of who I am. I have two dogs of my own (ages 8 and 3) who mean the world to me, so I understand how important it is to leave your pets with someone you can fully trust. I have experience giving medications and following care routines, as both of my dogs are on daily medications. I’m patient, attentive, and always make sure pets feel safe and comfortable, especially when they need extra care. I’ve also cared for senior dogs and understand the slower pace, extra gentleness, and attention they need. I treat every pet like my own, with love, patience, and calm energy so you can feel at ease knowing they’re in good hands. I have a very flexible schedule and am available most days and times. The only times I’m in class are Tuesday and Thursday mornings/afternoons, but I’m still available before and after school on those days. I’m happy to work around your pet’s routine and accommodate last minute needs whenever possible. Just let me know what works best for you, and I’ll do my best to make it happen! When caring for pets in their own home, I focus on keeping their routine as normal and comfortable as possible. I follow all instructions closely, including feeding schedules, medications, walks, playtime, and any special needs. I make sure your pets feel safe, loved, and calm by giving them plenty of attention while also respecting their space. I keep their environment clean (food areas, litter boxes, accident cleanups if needed) and always double check doors, gates, and safety precautions. I also send regular updates, photos, and messages so you can relax knowing your pets are happy and well cared for. I treat every home with respect and every pet like my own.

“Attentive, patient and communicative during our house sitting booking. Would book again!”

Megan B.

“Michael was fantastic! Our girl Haley loved her time with him! This was evident from the multiple text messages and photos that he sent to us. He was very easy going, prompt & followed all instructions perfectly. We will definitely ask him to care for Haley in the future. His love for animals shines through- we feel fortunate to have found him!”

Lauri N.

“Alexxis was wonderful with our dog Maddie. She was very communicative with planning and sharing photos/updates and flexible when our drop off time changed and with dropping of Maddie at our home. Would recommend and use again!”

Chelsea K.

“Busara is the best! Maxwell has a great time and is always well cared for! I have no worries when I’m not there because I know Busara is always there to save the day and make sure Maxwell has great company”

Ryan G.

About: I have cared for cats for most of my life but 5 years ago my fiancé and I adopted my first dog. For the past 5 years, I’ve cared for my dog, Mary Jane, who has been my sweetest teacher in understanding dog behavior, routines, and communication. Through caring for her, I’ve gained hands-on experience with daily walking, feeding schedules, basic training reinforcement, administering simple medications, and creating a calm, consistent environment for a happy pup. I have also cared for many friends pets while they were away on vacation. I may be new to Rover, but I’m not new to being a responsible, attentive animal owner. Caring for animals is already woven into my daily rhythm. I work part-time with flexible hours, giving me plenty of space in my schedule for peaceful walks, playtime, and check-ins with pets. I’m used to creating a balanced routine around my own dog, and bringing that same calm, attentive energy to other pets feels completely natural. I am currently free to sit/walk any day of the week. When caring for pets in a client’s home, I focus on creating a safe, calm, and familiar environment for them. I follow your routines exactly as you outline them — from feeding instructions to walk times to any training cues your dog is used to. I keep doors and gates secured, monitor their body language closely, and make sure they always have fresh water and a comfortable space to relax. Trust is extremely important to me, so I communicate clearly, send updates/photos, and treat your home with the same respect and care I treat your pet.

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!

“Brina took great care of our 10 y/o boxer when housesitting recently! She kept us informed and up to date. She took him on his favorite walk everyday and he seemed to be his fun, goofy self with her. Highly recommended!”

Sara B.

“We loved Tre! From the minute he pulled into the driveway, we felt comfortable that he would be a great fit to care for our enthusiastic pittie mix. He asked pertinent questions and took detailed notes during the meet and greet. Our dog responded so favorably to him and the became fast friends. We highly recommend him and will definitely be working together in the future.”

Alissa M.

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 got my first dog ever a decade ago and I raised him to be perfect, with no professional training for either of us. Then, I quit my ten year career in digital marketing to follow my passion and work entirely with dogs. I worked as a bark ranger at Bark Social and made dog safety my top priority, followed by (I cut humping down considerably). I loudly advocated for a transformation of safety rules while I worked there. I volunteer at BARCS and am aiming to get advanced training for different dog behavior needs. I got my first dog, Howie, a decade ago. I raised him without training and he is the best boy in the world. He’s my top reference. I adopted my second dog (Shadow) after instantly bonding with her at my old job. Shadow is bonkers and her parent has health issues, so Shadow needed a home where she can be her true self. Dogs are my world and I will give your pet all the love and affection they deserve (which is all of it because they are perfect). I quit my ten year career in digital marketing to follow my passion, dogs. Dogs run my life and I wouldn’t have it any other way. The only thing I can see myself doing for the rest of my life is working with animals. I’m all in so I’m available most hours and most days. I’m literally with my dogs 95% of my life so dogs are my daily routine. They’ll get over it if I spend some time with your dog though. But they’ll love becoming best buddies with any pet that boards or does daycare with them! All boarding, daycare, and walking clients will have a tracking chip affixed to them for the duration of our time together. I use a hands free leash attached around my waist so they’re stuck with me. I also use their handheld leash as a backup. I have a shared balcony and private fenced back patio, so there is always a secure outside area for your dog. My house is less than a block from Patterson park, giving them plenty of outside opportunities. I have two extremely friendly dogs, so there will always be friends for your pet. Dogs run my household and life revolves around them. Your dog is in safe and loving hands whether I’m walking, visiting, or boarding them. I love this community and plan on staying here for the rest of my life. Help me eventually buy a house here and you’ll have a walker/sitter for life!

About: 🐾In-Home Pet Care! 🐾 Hello pet parents! My name is Brianna Cummings and I'm excited to offer professional pet sitting services right in the comfort of your own home. With a deep love for animals and a commitment to excellence, I offer comprehensive care tailored to meet the unique needs of your furry family members. 🏠 About Me: As a dedicated pet lover, I understand the importance of maintaining your pet's routine and environment while you're away. Whether you're heading out of town for work or going on vacation, you can trust me to keep your furry friends happy, healthy, and well-loved in the familiar surroundings of their own home. 🐾 Services Offered: * Feeding & Watering: I'll make sure your pets are well-fed and hydrated according to their usual schedule, including any special dietary requirements they may have. * Dog Walking & Exercise: Your pups will enjoy plenty of outdoor adventures, whether it's a leisurely stroll around the neighborhood or an energetic romp in the backyard. * Playtime & Enrichment: From interactive games to cuddle sessions, I'll provide plenty of mental and physical stimulation to keep your pets entertained and engaged. * Medication Administration: If your pet requires medication, I'm experienced in administering oral medications, injections, and other treatments as directed by you or your veterinarian. 📸 Regular Updates: I know how important it is to stay connected with your pets while you're away, (I know from my experience) so I'll send you regular photo and video updates to keep you informed on all the fun we're having together. 🤝 Meet & Greet: Before booking, I'd love to schedule a meet and greet to get acquainted with you and your pets. It's a great opportunity for us to discuss your pet's routines, preferences, and any special instructions you'd like me to follow. 🔒 Trust & Security: You can rest easy knowing that your home and pets are in good hands. I'm committed to maintaining the highest standards of care and professionalism, ensuring a safe and stress-free experience for both you and your furry family members. And please Don't never hesitate to reach out if you have any questions or would like to schedule pet sitting services for your beloved companions. I can't wait to meet you and your pets! My schedule allows for pet care on weekdays after 3 PM and flexible availability on weekends. I prioritize scheduling pet care activities, such as feeding, walking, and playtime, around these times to ensure consistency and meet the needs of each pet. This structured approach ensures that pets receive the attention and care they deserve, while also accommodating the client's preferences and schedule. Ensuring safety, trust, and a comfortable environment for pets in a client's home is paramount. I prioritize familiarizing myself with the pet's routine, preferences, and any special needs. This includes following feeding schedules, administering medications if necessary, and providing ample exercise and playtime. I maintain a clean and hazard-free environment, securing doors and gates to prevent escapes and removing any potential dangers. Regular communication with the client helps build trust, as I provide updates on their pet's well-being and address any concerns promptly. Additionally, I respect the client's home by adhering to their rules and maintaining confidentiality. Overall, my goal is to create a secure and nurturing atmosphere where pets feel happy and loved in their own environment.

“Very pleased with the quick confirmation of a last minute request. My dogs were very happy and well taken care of when I got home. Cassie kept me updated with pictures and notes about their progress. Will definitely solicit help from her again ?”

Victoria U.

About: Hello I’m Sierra Duman and I started on Rover when I was a young college athlete at Wilkes University looking to make a little money and spend time with some fun furry friends. I have grown up with dogs since I was 3 years old. I currently have a 13 year old pit bull here in Delaware that I have raised since she was 13 weeks old. I have volunteered at our local SPCA’s and for my parents friends shelter. I love caring for dogs and I know for some people it can be hard working 9-5 or just working late hours and not being able to let your pup out or to feed it. I’d love to help anyone and everyone take care of their pup, so please consider hiring me for any of your pup needs! I am currently unemployed so it fits in my schedule at all times. I am currently looking for a job but when I get one I will update that on here! I have lots of roaming space in my back yard or and plenty of toys. I always bring my dog outside with me whenever I tend to our other animals. She’s on a feeding schedule to maintain her weight. And she is very much so loved.

About: I will take care of your pets as I would my own. I currently have three rabbits and a cat of my own. Over the years, I have provided pet sitting services for many clients, primarily caring for dogs. You can reach out to me at any time during the period that I am looking after your pets. This is my side job, I am a professional photographer as well but if I get a request I will accept to the first of my availability! Is my house equipped with a large mansion for my rabbits, where they are free to roam. As of your home i will go as your home rules are.