House Sitting Chesterville

About: Welcome to C & L’s Cozy Dog Retreat 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 working with anxious dogs & dogs in shelters also (as a volunteer). I love taking dogs for walks, playing with them, & give them attention. I limit the number 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 for your pups' boarding. I am available 24/7, Monday-Friday. I accept boarding and doggie daycare on a limited basis. Please message me if you are interested. This ensures I can give each pet the attention they need while ensuring safety. I am also happy to do multiple check-ins a day while your friend stays in their familiar home. I have a fenced yard and 2 friendly dogs. I can also kennel your dog if needed. A meet-and-greet with the dogs would be required before any overnight stays with us. Also, proof of immunizations.

About: Welcome to Safe Hayven Fields At Safe Hayven Fields, we’ve created more than just a place for pets—we’ve created a peaceful sanctuary where every furry friend is treated like family. Nestled on our beautiful horse farm in lower Cecil County, our little slice of paradise offers breathtaking views, fresh country air, and plenty of room for adventure. Whether your pup loves splashing in the pool, running and playing in our safe, clean, and secure outdoor spaces, enjoying cozy snuggles inside, or taking a stroll to visit the horses, every day is filled with love, fun, and personalized care. We believe the most important thing we can give your pet is love. We care for each guest as if they were our own while always respecting and following every parent’s wishes, routines, and special instructions. Your pet’s happiness, comfort, and safety will always come first. Our hope is that Safe Hayven Fields becomes your pet’s home away from home—a place they’ll be excited to return to, with wagging tails and happy hearts every single visit. We can’t wait to welcome your family into ours. ❤️ My entire life revolves around my farm and caring for all of my animals. I am on the property 24/7 as this is my full time job. And luckily it’s my passion. We have a beautiful fenced in pasture with lots of space to run. We are in a very private and rural area. We also have a pool- only if parents are OK and the Pup chooses to take a dip! Your Pup will always be supervised. If there are restrictions we will always abide by them. We also have dog crates if needed or requested and a beautiful inside area as well. Basically your Pup is gonna have free range and feel a home away from home.

“Claire is a sweetheart and took care of our 3 pups all day. They were happy and tired out when we got back. Definitely recommend Claire!”

Amanda M.

About: I’ve been pet sitting since 2018 and have experience caring for cats, dogs, and birds. I currently have a cat and a bird of my own, and I’ve also had dogs in the past. I’m an Agriscience Education major and took Animal Science in high school, so I’ve always had a strong interest in animals and their care. I’m comfortable following feeding routines, cleaning litter boxes and cages, giving medications when needed, and making sure pets get plenty of attention and playtime. I know every pet has their own personality and routine, so I take the time to make sure they feel comfortable, safe, and cared for while you’re away! I’m a college student, so my schedule can vary depending on my classes, but I have flexibility throughout the week for pet care. I’m able to plan visits around my class schedule and make sure pets receive the care and attention they need. I’m also happy to communicate ahead of time to work out a schedule that fits both you and your pet! I treat every pet like they’re my own and make sure they are in a safe, comfortable, and clean environment. When caring for pets in a client’s home, I follow their normal routine and any specific instructions they leave for me. I’m respectful of your home and always make sure doors, gates, cages, and other areas are secure before I leave. I also understand that some pets can be nervous around new people, so I’m patient and give them time to get comfortable with me. My goal is for both you and your pets to feel safe and confident while you’re away!

About: Hello everyone! I am an animal lover, I grew up around animals all my life. Our furry friends are extended family members. I hope you entrust me with your furry loved ones. I am currently an active college student, but I have somewhat situated myself with a work-life balance. I am available and flexible for weekdays and weekends! I currently have a kitten almost a year old. Having him has taught me patience, and having complete responsibility. Milo is my profile picture! I feel as though I am completely up to any challenge, I hope I can help with your furry loved ones!

About: I have lots of compassion when it comes to animals, and I have years of experience working for cat/dog rescues as well as pet transports, I currently have a four day weekend at my current job and have way too much free time! I also have no problem with early mornings or late nights! I have two small dogs that I take for a couple walks a day, and I Help prepare their food which is home made and all natural. I also have a cat with urinary tract issues so I’m used to keeping their litter boxes spotless.

About: ✨ Schedule & Availability I currently maintain a full-time position but please do not hesitate to reach out and we can talk about options to accommodate your pets needs. ‼️Currently can only guarantee afternoon services on Monday and Tuesday. ✅House sitting includes Morning and Evening services with overnight care. ✨My Experience I have experience caring for both dogs and cats with a wide range of personalities, energy levels, and care needs. In addition to caring for my own pets over the years, I have multiple years of providing care to clients, and volunteered with animal rescue and shelter organizations. I currently work full-time, but I still maintain availability outside of my work schedule for pet care, drop-ins, walks, feedings, and quality time with your pets. I’m reliable with routines and make sure pets receive the attention, consistency, and care they need while their owners are away. I understand how important trust is when someone is caring for your pets and entering your home. I treat every animal with patience, respect, and attention to their individual comfort level and routine. I’m experienced with shy pets, senior animals, anxious pets, and pets that may need a calmer approach or extra time to adjust. I always prioritize safety, clean environments, secure doors/leashes, and careful attention to instructions so owners can feel confident their pets are being cared for like family.

“Krose had a great day with Chelsea! Chelsea arrived early with a goodie bag with treats and a toy. We appreciated the photos throughout the day. We were happy to see he was relaxed when we arrived home. We would definitely use Chelsea again!”

Jeanne S.

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.

“This was the first time Lydia watched my 3 pups. She is very nice and I felt comfortable at the meet and greet. I knew she would take great care of them. She gave updates and assured me they were fine. My female dog was struggling when I first left , Lydia gave her extra love. Now that I am home, I think my Bailey is missing Lydia. I will definitely reach out to her in the future.”

Lisa H.

“I was only away for the better part of two days and one night but really appreciated that Chris texted updates and sent lots of pictures letting me know my sweeties were safe and happy. She even washed the sheets and remade her bed before she left!”

Carol S.

About: Hello furry parents! My name is Lily and I’m excited to support you and your family. I have worked with all dog breeds and all ages through fostering. I am currently in my training certification program to provide proper education to you and your puppers. I am an online student looking to spend my free time with amazing pets. My top priority is to give all animals time and love. Whether it’s giving a long walk, using my dog park at my complex or administering medication, I’m your girl! When I would care for your pets, it’s all about the greeting. I would love to make sure your pets are as comfortable with you as for me! If you’d love me to help them learn tricks, feel free to request!

About: I am here to take of your dog and to provide them the love they long when it’s vacation time for owners (or anytime you need to yourself). Provide exercise for dogs (usually in half-hour or one-hour increments). Pick up and dispose of dog droppings during walks. Check dogs' food and water supply to make sure basic needs are met after walks. I am very patient and show a lot of compassion towards dog. I just want them to feel at home away from home! I am also a very active person, so your dog will be able to have all of their fun they usually have or more when they are with me! I hope to walk your dog soon! Prices are non negotiable I am working from home currently. This will allow me to give your first baby all of the attention they desire. Please ask me any questions on any accommodations that we may be able to work out. I don’t have any pets of my own so if your fur baby isn’t fond of other pets they can feel secure being over my home. My I am close with my neighbors who do have friendly pets as well, so if your pet loves company, they can be easily accommodated. We also have a dog park walking distance from the complex

About: I love dogs and I love spending time with them and playing with them! I love to snuggle or lay close with them and make sure they are comfortable at all times. I love playing with them and wearing them out so they sleep good at night! I love walking them and seeing how excited they get when someone comes to see them! I have dog sat many of dogs from very small to very big and I don't have a type, I love all sizes, shapes, and more! I have had a dog my whole life and I can't ever get enough of them. I have been told that I am good at dog sitting and their pets are always great when they return!

About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.

About: With years of hands-on experience caring for dogs, cats, and everything in between, I treat every pet like family. Whether it’s a high-energy pup who needs long walks or a shy senior cat who just wants a cozy lap, I tailor my care to each animal’s unique personality and needs. I’ve worked with pets of all ages, sizes, and temperaments—including those with special medical or behavioral needs. From daily walks and playtime to overnight stays and medication administration, I provide dependable, compassionate care that gives pet parents peace of mind. Your pet’s safety, comfort, and happiness are always my top priorities. I’m here to make tails wag and whiskers twitch—while keeping you updated with plenty of photos and messages along the way! I'm currently working part time so I have plenty of time to play with you pet. I am available after 2pm throughout the week and my weekends are open. My space is designed with your pet’s comfort and safety in mind. With space to roam, nap, and play, your furry friend will feel right at home from the moment they arrive. I offer a clean, secure, and peaceful environment—free from hazards and full of love. Whether it’s a quiet corner for a cat to curl up or a fenced yard for dogs to stretch their legs, I’ve created a space that caters to all personalities and energy levels. Pets enjoy supervised playtime, cozy sleeping areas, and a calm atmosphere that helps ease separation anxiety. I maintain a consistent routine, provide fresh water and clean bedding daily, and ensure every guest receives personalized attention. Plus, I’m always happy to send photo updates so you can see just how relaxed and happy your pet is during their stay.

About: Hello! My name is Teresa! I work full-time on the weekdays but I have weekends free for dog sitting. I have been a dog sitter for a few of my neighbors in the past for fun. Your dog(s) will have a nice house to run around in, we'll take long walks around the neighborhood, going to the Bowers beach, playing in the sand. Since its only me in the house, they will have my undivided attention and love. In the summer, they will be cool, and in the winter, they will be warm by the fireplace. I truly enjoy the company of pets and I look forward to providing you peace of mind and the utmost in care for you and your four legged family members!

About: I am a mature and reliable pet sitter with a preference for cats but will also be happy to provide care for small dogs or other animals. I operate with a genuine love for all all animals and have a history of community service and donations to animal shelters and causes. I have been a cat owner for over 12 years and currently have one senior cat. When it comes to cat care, my extensive experience and commitment to feline companionship shine through. I specialize in socializing skittish cats, exercising larger cats, and soothing senior cats. I am detail-oriented, ensuring that your pets get the care and attention they are accustomed to, including medication management, grooming, and in-home care. I am proactive in communication and am also highly responsive, giving pet-owners piece of mind. But that's not all – my versatility extends to caring for dogs as well. I bring the same level of dedication and expertise to canine companions, ensuring they receive the love and attention they deserve. Whether it's daily walks, playtime, or adherence to dietary requirements, I'm well-equipped to provide comprehensive care for dogs of smaller sizes. With me as your trusted pet sitter, you can confidently leave both your cats and dogs in capable hands. Your pets' happiness, safety, and well-being are my top priorities, and I take pride in delivering exceptional care tailored to their individual needs, whether they're four-legged felines or canine companions. My schedule is flexible and can accommodate most requests with enough notice. While I can provide care for your pet in your own home, I am also available to host your pet in my home. I have a one-level home with hard wood floors (for easy cleanup) and pet-proof furniture. I do not let animals outside unattended so if you have a cat that likes to wander outside, I will not be comfortable allowing that

“She was great and my dogs loved her!”

Cathleen T.

About: I grew up with rabbits and various small pets. My first dog, Toto, was trained by me in elementary and middle school. Now, I spend my evenings caring for others animals whenever possible! I work 7:30 am to 3 pm as a teacher! My day does allow for a mid day visit, distance depending! Free every evening for walks and lots of attention! Experienced with crate trained dogs and more free range styles. Love building trust with animals and keeping their days typical and calm while their owners are away!