Dog Boarding Winchester

“Anytime I asked about my girl I got an update and pictures sent! She loved her stay! Madison did awesome with her and we will be booking again!”

Kristen C.

“Ana was wonderful! Very loving and caring. My furbaby became very attached to her husband as well. She also liked playing with Mia, Ana’s fur baby, which was awesome. She is usually indifferent to other animals. I would highly, highly recommend Ana. It was such a comfort knowing Ruby was being loved while we were away ❤️”

Alana V.

“Our pup appeared to be very content under Kirsten’s care where she had a 24 hour stay. Kirsten was a great communicator and provided pictures and texts that aided in easing the worry of leaving our sweet girl with a total stranger! Thanks for everything.”

Susan E.

“Dana was super communicative and a wonderful host! I never felt like I was missing out on Poppy’s day with her, and despite Poppy’s young age, she handled her very well. I would definitely recommend her!”

Emerson H.

About: About Me Animals have always been a huge part of my life, and caring for them isn’t just something I enjoy—it’s something I do professionally. I own a pet-sitting business serving Central Kentucky. I have extensive hands-on experience caring for dogs, cats, and horses of different ages, sizes, personalities, and needs. I’m comfortable with multi-pet households, senior pets, animals with special routines, and pets who need a little extra patience to become comfortable with someone new. I’m also a lifelong animal owner myself, so I understand how important it is to find someone you genuinely trust with your pets. I pay attention to the little things—changes in appetite, behavior, bathroom habits, mobility, or anything else that seems unusual—and I believe in keeping owners updated so they can relax while they’re away. What You Can Expect I’m comfortable following detailed feeding and care instructions, maintaining your pet’s normal routine, walking dogs, cleaning litter boxes, providing playtime and companionship, and giving each pet the individual attention they need. I especially enjoy working with animals who may be shy, particular, anxious, or simply need time to decide that a new person is trustworthy. I don’t expect every pet to immediately love me—I’m happy to earn their trust at their pace. Safety & Communication Your pet’s safety comes first. I follow owner instructions carefully, keep a close eye on the animals in my care, and communicate promptly if I notice anything concerning. You’ll also receive updates so you know how your pets are doing while you’re away. I know how difficult it can be to leave your pets in someone else’s hands. My goal is for you to come home to happy animals who have been well cared for and whose normal routine has been disrupted as little as possible. Whether you have one spoiled house cat, an energetic dog, a senior who likes to take things slowly, or a whole household of four-legged family members, I’d be happy to care for them. Although I work as a substitute teacher, there are many days I am home part or all of the day. While I have a generic routine, I like to know the pets usual routine so I can cater to that as much as is possible. I have a small fenced yard, but most importantly, my apartment is set up with pet safety in mind. I have gates and latches to prevent accidental runners, my cat has her own space to keep away from other animals, I have the space and ability to separate dogs if needed. Ultimately I treat them like my own. They are welcome in my bed, have free run of the common areas, have lots of toys... I am always up for snuggles and fun!

“Sable had an amazing time at Cheyenne's, surrounded by her incredible family and their wonderful dogs! She absolutely loved every moment of it!”

Louis D.

“Second time having Booker and Milo stay with Kelsey and we couldn’t have asked for better care for our boys. She always sends updates and lets us know how they are doing. 10/10”

Tyler S.

“Our pup seemed to really enjoy her time with Leilani and her pups. For my part, I was grateful for consistent communication, last-minute availability, and flexibility.”

Alana G.

“We will definitely being using Kimberly’s services in the future. She was great! We are so thankful for the daily updates and the peace of mind knowing that she was in such good hands while we were away. Thank you so much for taking care of our little ball of energy.”

Heather C.

About: Kayla: "I grew up with numerous horses, dogs and cats. I've worked at couple pet boarding hotels and the Lexington Humane Society, so I can make sure all of your pet's complex needs are met. I'm not a certified trainer, but I have a lot of experience training horses and dogs (you'd be surprised how much they have in common). More recently, I have been training our Aussie Bandit, which has been a challenging yet rewarding adventure. I believe strongly in positive reinforcement and have read numerous training/pet psychology books to be the best dog mom I can be." Brandon: "My family grew up with a Shiz-Tzu/Maltese mix. I have pet sit numerous of my friend's pet throughout college. Shortly after college, I rescued a dog (unknown pit mix), whom was my companion until Kayla and I met then he became our companion. We would go on walks, roller-blades, runs, and travel the country. If a dog could go on the adventure, he came along. His life was full of love, given and received, and we're ready to open our home to share that love with your dog." Together, we've been dog parents for 10+ years. Brandon works from home and is nearly always available. Pets are allowed on furniture, though not our bed. Snuggles are mandatory. Enrichment is available however your dog prefer: walks, runs, ball in the yard, socialization at the park, mental stimulation treat toys, you name it. Brandon works from home and can let dogs out as frequently as needed during the day. When we're both off work, we tend to do enriching activities with our dog. On weekends, we tend to stay close to home, or take our dog on enriching activities (farmers market, park play, walk) and are happy to bring your dog along if it makes sense to. We have a small fenced in yard, good for bathroom breaks and small play. No children in this house, and we keep the space generally clear for dogs to be able to run/move around. The couch is a fan-favorite for snugglers. We're nice and close to Masterson Station dog park, if your dog needs more space and/or likes to be social.

About: I’ve taken care of dogs my entire life, from owning miniature schnauzer’s and golden retrievers to even raising my own litter of 11 golden doodle puppies. I know how to give dogs the special and individual attention they need as well as making them feel loved. I’m currently a full time student, but I have a lot of gaps in my schedule to fill. I’m available almost anytime during the week, except for Thursday right now. I live in a condo by myself and have a lot of free time so I can make sure every pet feels comfortable and cared for in their environment. I appreciate any specific instructions from their owners to make sure they stick to their routines.

“Maggie is sweet! Our dog seemed to have a great time with her, her dog, and cats. Her dog took a bit of time to warm up to our dog, but it seemed they became good friends shortly thereafter.”

Leslie P.

“Haley made me feel so safe leaving my dog with a stranger. I was updated with pictures and activity through the day and it made it so relieving.”

Bailey V.

“She was great! Kathryn was incredibly friendly and sent lots of pictures and updates about our dog while she was staying with her. I also very much appreciated that we set up an initial meeting with myself, my dog and Kathryn to make sure it was a good fit for everyone. We will definitely being using her services again! ?”

DeAnna S.

“Justin was great! Sent updates and was flexible with pick up and drop- off times, which I really appreciate. Would definitely recommend”

Karah M.

About: I have always had a huge love for dogs and have years of hands-on experience caring for dogs of all ages, sizes, and personalities! I volunteer as a trainer with 4 Paws for Ability, where I have fostered, trained, and served as the primary handler for three dogs. Through this experience, I gained valuable skills in obedience training, puppy development, understanding dog behavior, and providing consistent, loving care. Outside of 4 Paws for Ability, I've also been a regular pet sitter for multiple families, caring for their dogs and building trusting relationships with both the pets and their owners. Both through 4 Paws and individually I've cared for dogs of all ages, including puppies as young as 8 weeks old, as well as dogs with special needs and conditions such as hip and elbow dysplasia and dogs in heat. These experiences have taught me how important it is to understand each dog's individual needs and adjust my care accordingly. One thing I especially enjoy is helping dogs maintain and build upon their existing training! I'm happy to reinforce commands, routines, and positive reinforcement techniques that families are already working on. I understand how important consistency is, especially for puppies and dogs actively learning new skills. Whether your dog is full of puppy energy, needs a little extra attention, or simply enjoys a relaxed routine, my goal is to make them feel safe, comfortable, and loved. I know how much trust goes into leaving your dog with someone else, and I'll always treat yours with the same love, patience, and attention I would give my own! I'm currently a college student with a very flexible schedule! My classes are solely in the mornings and last no more than 2.5 hours (even when back-to-back), leaving me with plenty of time throughout the day to dedicate to pet care. I have lots of availability for walks, playtime, potty breaks, and giving your pup the love and attention they deserve! My weekends are also very flexible, allowing me to spend even more quality time with your pup and accommodate longer stays. I'm always happy to work with your dog's usual routine to make sure they feel comfortable and cared for while you're away! Your dog's safety, comfort, and happiness are always my top priorities! I live in an apartment complex with a large, fully fenced-in dog park, providing plenty of space for exercise, playtime, and fresh air. Depending on your dog's personality and preferences, they can enjoy socializing with other dogs or have their own time to run around and play without other dogs present. I always prioritize safe interactions and will never force your pup into an environment they're uncomfortable with. I also have plenty of dog toys to keep your pup entertained, whether they love playing fetch, chewing on toys, or just having something fun to play with! I have a crate available if your dog is crate-trained or feels more comfortable having their own space. I'm happy to follow your dog's usual routines, including feeding schedules, potty breaks, exercise, and any ongoing training. With my experience handling and training dogs, I understand the importance of consistency, patience, and paying attention to each dog's individual needs. When caring for pets in a client's home, I make sure to respect their space and maintain their dog's familiar routine as closely as possible. I also love keeping owners updated with pictures and messages so they can feel confident that their pup is safe, happy, and receiving plenty of love and attention while they're away!

About: Hi! I'm a 32-year-old lifelong dog lover with years of hands-on experience caring for dogs of all personalities, sizes, and needs. I've had dogs in my life since I was a child, and I've spent years dog sitting for friends and family. I'm also a proud dog mom to my Australian Shepherd, Nimbus, who I've had for five years. Nimbus is a special-needs dog, so I've learned firsthand how important patience, consistency, attention to detail, and understanding each dog's individual needs really are. I take great pride in making sure he's happy, healthy, comfortable, and well cared for. Being a responsible pet owner is something I take seriously. I understand that trusting someone with your pet is a big deal, and I want you to feel just as comfortable leaving your dog with me as you would with a trusted family member. I'm dependable, attentive, and genuinely passionate about animals. I also have my own reliable transportation, making it easy for me to accommodate pet care needs. Whether your dog needs walks, playtime, feeding, companionship, or a little extra patience and attention, I'll treat them with the same love and care I give to my Nimbus. Your pets deserve more than someone just showing up to feed them. They deserve someone who genuinely cares. And that's exactly what I offer! 🐶❤️ I have open availability for sitting, boarding, walking, feeding, playtime or whatever your pet needs! I would love to even take your dogs to the dog park and maybe get a pup cup! I have a large fenced in back yard and I live in a nice and safe neighborhood. I can call, FaceTime & take pictures for you anytime, so you know your dog is happy & safe!

About: Hi! I’m Evelyn, a veterinary technician with 8 years of hands-on experience caring for dogs and cats of all ages, sizes, and personalities. Caring for animals isn’t just my career—it’s something I truly love. Working in veterinary medicine has taught me how to recognize when pets are stressed, uncomfortable, or not feeling their best. Whether your pet needs medication, a fun walk, overnight companionship, or just a little extra patience, I’ll care for them like they’re my own. Every pet has a unique personality and routine, and I enjoy taking the time to get to know what makes them happiest. I’ll keep you updated with regular photos and messages so you can relax knowing your pet is safe, comfortable, and in caring, experienced hands. My schedule works well for pet care because I have a consistent full-time routine and a one-hour lunch break that often allows me to check in on pets or provide midday visits when needed. Outside of work, I love staying active through running and daily walks, so I enjoy keeping dogs happy and engaged while always matching the pace to each pet’s age, energy level, and needs. I’m available for walks, drop-in visits, house sitting, and pet care throughout the week and on weekends. My goal is to provide dependable, compassionate care while keeping your pet’s routine as consistent as possible. Your pet’s safety, comfort, and happiness are my top priorities. As a veterinary technician, I’m trained to recognize signs of stress, illness, anxiety, and changes in behavior, but I also know that the best care often means helping pets feel relaxed, secure, and loved. I live in a pet-friendly apartment with my friendly dog and make sure every pet receives plenty of attention, exercise, potty breaks, and supervision. I’ll follow your pet’s routine closely, whether that includes feeding schedules, medications, or crate training, and I’ll always keep you updated with photos and messages so you know how they’re doing.

“We have used Kristin several times now and she is truly the best. Our most recent trip ended with an emergency and she was so helpful with our pups while I was handling family needs. I never have to worry about my pups when they are there.”

Hannah P.

About: Hi! My name is Ally! I grew up with both cats and dogs, and I have a 3-year-old Australian Shepherd–Border Collie mix of my own who loves animals and playtime. I live by myself in a big apartment, giving me plenty of space to care for pets comfortably and provide them with a safe, welcoming environment. I’m currently a professional soccer player, and my schedule gives me plenty of free time. I’m typically finished with training by noon, leaving the rest of my day open to give your pets the love, attention, and care they deserve. We love long walks, and I’m happy to include plenty of exercise, playtime, or simply companionship in their routine. I’ll make sure they feel happy, comfortable, and well cared for while you’re away. I understand how important it is to trust someone with your pets, and I’ll always treat them like my own! I’m currently a professional soccer player, so I have a pretty flexible daily schedule! I’m typically finished with training by noon, leaving the rest of my afternoons and evenings free. This gives me plenty of time for walks, playtime, potty breaks, and making sure your pets receive lots of love and attention throughout the day. I also have a dog of my own, so caring for animals is already part of my everyday routine! I live alone in a spacious two-bedroom apartment with my friendly 3-year-old Australian Shepherd–Border Collie mix, who loves having other animals around. I’ll do everything I can to make your pet feel comfortable, safe, and right at home. I’m happy to follow their usual routines, feeding schedule, and any special instructions you provide, while giving them plenty of exercise, attention, and affection. I’ll also send regular pictures and updates, so you can feel reassured knowing your pet is happy, well cared for, and in good hands.