House Sitting Sassafras

“Absolutely loved Ciara and so did my babies. I highly recommend her as she is attentive and loving. She gave great updates and really made sure my kids were as comfortable as they could be.”

Samantha M.

“Rebecca did an excellent job staying at our home with Pippin! She was really prepared with questions to help the weekend good smoothly and to understand his needs. She was very responsive to messages and sent detailed updates and pics. Our pup had a great time!”

Leah O.

“Courtney was an amazing help with sitting Maxwell today. She was punctual, early in fact ;), followed all requests and most of all, made sure Maxwell was in good company. Communication was great and I felt confident that my little man would be in great care with her! We will be looking to have Courtney back in the future for sure. Thanks!”

Ryan G.

“This was my first time using a dog sitter and Robyn went above and beyond. Incredibly attentive and provided frequent updates. My dogs absolutely loved her. Can’t recommend her enough!”

ani p.

“Lydia was great! She sent pictures of our dog / updates and took great care of him. Highly recommend her!”

Sierra H.

“Nina was awesome, she was always on time when we met up, took care of Roo and the house the same way i would. House was just the way we left it. Roo definitely made a new best friend and we found out house sitter for the future, she sent us pics and updates on how things were going and she even sent pictures of the snakes. Lol. Couldn't go wrong booking with Nina if you need a house sitter, will definitely be using her in the future.”

David C.

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.

“Reid is definitely a wonderful doggie sitter! He sends pictures and updates regularly and our little lady, who doesn't trust most people, actually sat and watched a movie with him! So, he is A OK in our book!”

Shauna L.

“Busara was a delight! She gave a lot of feedback on her time with Jasper. Jasper seemed to enjoy having her here. I’d definitely ask her to come another time!”

Lois D.

“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.

“I was going to be away on a 15 day vacation in Europe and concerned I wouldn’t be able to find a someone I could trust to care for my two young cats for such a long time. Any and all worries melted away when I met Jen! She is very personable, very reliable and caring. Jen sent me daily updates on my kitties interactions with her and lots of photos . I highly recommend her to care for your pet. I will definitely continue with Jen for taking care of my fur babies 😊”

Barbara M.

About: I’ve fostered shelter dogs and taken care of small puppies from a young age. As a healthcare worker, I’m cpr certified, caring, compassionate and attentive. Book me for your furry friend! I work full time as a phlebotomist and have ample time on the weekends to dedicate to your pet. I will ensure they have a fun time on their walk. Growing up, I walked my family dog and ensured that he got his meals and walks. It gives me so much joy to meet clients’ dogs and take care of them as if they were my own.

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.

“Taylor is a huge help and Maxwell loves spending time with her! She is attentive and makes sure Maxwell is entertained and has someone to snuggle with during the day. 10/10 for sure!”

Ryan G.

About: With over six and a half years of hands-on pet care, I bring a rare blend of experience, attentiveness, and heart. I’ve worked with dogs of all sizes, temperaments, and ages—from energetic puppies learning the ropes to senior pets needing gentle, attentive care. What truly sets me apart is my ability to read and respond to animals’ unique personalities. I create a calm, consistent environment where pets feel safe, loved, and understood. Whether it’s administering medication, offering leash training for puppies, or providing low-stress companionship for older pets, I bring patience and skill to every interaction. I also have experience caring for a diverse range of animals beyond just dogs and cats. From chickens and birds to hamsters and other small pets, I understand that every species has its own rhythm, needs, and comfort cues. I’m confident and compassionate with unique, exotic, or less-common animals, always prioritizing their safety, emotional well-being, and daily routines. Pet care is a built-in part of my weekly life. I’m highly flexible and genuinely enjoy working around each pet’s needs and schedule. Whether it’s early mornings, midday visits, evenings, or even late nights, I’m available and committed to making your pet’s care seamless and stress-free. I’m also happy to accommodate weekend bookings and unique timing requests whenever possible—just let me know what works best for you and your pet, and I’ll do my best to make it happen. Reliability, consistency, and clear communication are at the heart of everything I do. In clients’ homes, I prioritize maintaining their pet’s normal routine and environment. I follow all instructions closely—feeding schedules, walking routes, medication routines, and preferred playtime activities—so your pet experiences as little disruption as possible. I also make sure the space stays tidy and respected while I’m there. If I’m hosting pets in my home, I provide a calm, safe, and welcoming space. I separate animals as needed, keep food and water fresh and clean, and ensure they have access to cozy rest areas and supervised play. I never leave pets unattended, and I’m mindful of their comfort, especially in a new setting. In both cases, I focus on creating a low-stress, high-trust atmosphere, and I keep pet parents updated with messages, photos, and honest communication throughout the stay.

“Terry was absolutely Amazing!! She took great care of our 2 fur babies, sending photos and videos daily to update us on how they were doing while we were away. I was very anxious to leave our 2 cats with someone new, as our previous pet/house sitter is no longer in the business and we had not used someone new in many years, I have put off traveling due to this, much to my husband's dismay. I can say I was so relieved while away to see how great Terry was with our pets. I also think when we got home our house was cleaner than when we left! Terry did a fabulous job, she went above and beyond and now I'm ready to travel more feeling comfortable that we have found our new pet caretaker! I cannot recommend her enough!!”

Judy M.

About: What sets me apart is my commitment to providing safe, reliable, and compassionate care for every pet. I understand that every dog has a unique personality, routine, and needs, so I take the time to get to know them and make sure they feel comfortable and cared for while you’re away. I have experience caring for dogs of different ages and temperaments, including energetic puppies who need patience, consistency, and positive reinforcement, as well as senior dogs who require a gentler approach, slower walks, medication reminders, and extra attention to their comfort. I also prioritize clear communication by sending regular updates, photos, and messages so you always know how your pet is doing. Whether your dog loves long walks, playtime, or simply relaxing with company, I’ll make sure they receive plenty of attention, affection, and care. My goal is to treat every pet as if they were my own, giving you peace of mind while you’re away. I am in school night time and am available during the day. I am free all day Saturday and Sunday's. I can come whenever you need me to. When caring for pets, I always follow the routine they’re most comfortable with. In a client’s home, I make sure pets are fed on schedule, have fresh water at all times, get plenty of exercise, bathroom breaks, playtime, and lots of affection. I also keep their living area clean, administer medications if needed and instructed, and make sure they feel safe and relaxed while their family is away. I respect my clients’ homes by keeping everything tidy, locking doors, and following any special instructions.

About: I have always had pets. As a toddler my dog and I would explore the woods together. I have had pet birds, fish, hamsters, turtles, spiders, frogs, lizards, rabbits, horses, turkeys, chickens, cats and dogs. I also have experience caring for cows and sheep. I started doing pet care professionally as a teen. I eventually started training dogs as well. I did that until I moved for college. Now, I started providing those services in my home. Having dogs stay with me gives me the opportunity to provide 24/7 care and training. I trained my last dog to be a hearing dog. She always alerted me to the door and phone, so I incorporated those natural likes and abilities into her training. I'm currently preparing my new dog for search and recue training based upon his love of playing hide and seek. All dogs have their own natural abilities and like different things. I have used clicker training in the past. I usually use reward based training. I occasionally seperate dogs, so they might not play together unless they are from the same household. I have rooms set up as individual dog suites. I have lots of cozy blankets and toys for dogs to feel comfortable. Dogs will still roam and play throughout the house. Dogs will get lots of individual attention. Dogs usually make friends and enjoy playing together. There are lots of toys beds and blankets for them to get cozy and have fun. I have a large unfenced yard (will be fully fenced in October. Currently only one side is fenced.) that backs to woods with a creek and a park. Dogs will be leashed outside. I can take more than one dog and for extended stays. Dogs should bring their own food and potty training pads if they use them. I send lots of pictures of your dogs during their stay. I can send videos and have done live chat videos, so you can see and talk to your dog. Dogs will be taken outside regularly. Dogs will go outside in all weather at least 2 times during the day. Dogs also will have ample play time indoors with running, chasing, fetching or jumping. Dogs can play ball or nap. I take dogs running at the park. Each dog will be cared for according to his personality. Dogs get alot of individual attention. I make sure dogs are comfortable throughout the day and i play with them and incorporate them into my day as much as possible. My 2.5 year old son and husband also play with the dogs. They help train, feed and care for dogs too. They also run with dogs and take them to the park or dog park. Dogs may go to the store with us or on errands or on an outing. Dogs may sleep in our bed with us. Dogs may join in for Disney songs and dancing. Dogs may make new friends and bond. I only care for a few dogs at any given time. I can care for dogs weekly and monthly. I can cater to dogs special or individual needs. Drop off pick up is between 6am to 7am or 7pm to 8pm weekdays and anytime weekends. More About Me: I started pet care professionally more than 20 years ago, when i was studying nursing. I was in college and nursing school full time, working at a healthcare facility full time, doing home care and pet care. I received both of my undergraduate degrees in legal studies. I started 2 master's degree programs one in law and one in business. I plan to continue doctorate studies in psychology. My main interest is behavior. My other interests are sociology and anthropology. I also write. I love dog care. It's fun! Even when the work is hard, it's rewarding. I'm glad i decided to focus on dog care again. My days are much better with dogs in my life. More About My Family: My son has benefited from having dogs in his life and it has afforded him an early opportunity to begin working with animals. My son is an animal lover. He especially loves dogs. He's a good trainer and pet care provider. He has a deep concern for dog's feelings and goes out of his way to see them happy. He likes taking care of animals, especially dogs. He's interested in going to school, so he can learn more about taking care of animals. My husband loves dogs. He grew up with dogs and cared for additional dogs. He has a relaxed natural approach and does not use training as much as treats play and petting.

About: When I was around 8 I started volunteering at a barn simply because I loved to be around animals. I was constantly walking my neighbors dogs and my own. I now work at a boarding facility where I take care of dogs and cats. I love it and enjoy nothing more than making sure your pets are happy and cared for when you are not able to be there all the time. My friends and neighbors often ask me to watch their pets when they are away. My family currently has 3 rescue dogs, a cat and 3 horses. I look forward to the opportunity of caring for your fur babies!! I am going into my freshman year of community college and love the opportunity to be able to do something that I love in my free time I currently have 3 dogs that get along really well with each other and other dogs. I pay very close attention to how dogs act around each other and their environment to ensure they are safe.

About: From caring for 10 senior dogs at a rescue, to bathing dogs that got sprayed by skunks, to training and taking dogs on their own outings to parks and nature hikes, you name it I’ve done it! Even flying with dogs! ✈️ I have experience with all breeds, ages, and like to keep pet parents informed with notes & pics. Growing up in farm country taught me to love and care for all animals, but dogs and cats are by far my favorite. I also have experience in administering medications to our furry friends. I left my career of being a nanny in CA to move to the east coast to marry my husband. That was 2019, and I’ve been boarding/caring for animals since then. I’m currently a stay-at-home wifey so the dogs get 100 percent of my attention when they are with us. We live in a 3 story townhouse with a small unfenced yard in front of our home, to a large grassy area on the side of our home, to a giant green grass patch directly behind us just out our back door. The neighborhood is VERY dog-friendly with lots of sidewalks and comes complete with a dog park in walking distance. Our home is dog-friendly meaning dogs are allowed on all furniture and we even have doggie steps for little pooches to get up on our bed if they wish. We also have a 2mile + walking path near us. So we have plenty of activity options. We even have Pluto cartoons for your pet to watch! Pets get 100 percent of my attention when they stay with us. Their comfort and safety is my priority as I do pet care full-time. Our home has no place that’s off limits to your pets. If they want to snuggle on our bed or relax on our couch or even be in our guest room - they are more than welcome wherever they are most comfortable. We even have a massive bean bag most animals love thinking it’s a giant dog bed 😂.