Pet Sitting in Winchester

“Debbie was absolutely lovely. She took great care of my pups while we were out of town. I couldn’t have asked for anyone better! We video called ahead of time to go over the routine and she checked in with me while she was checking in on the pups. Have us absolute peace of mind! 10/10”

Matthew B.

“Dina is wonderful! The pups absolutely loved her and it was so nice to know that they were being checked on while we were gone for the day. I also got some really cute photos! I highly recommend Dina!”

Kelly S.

“We are so grateful for Chelsea! She has been medicating our cat while we are out of town and has done an amazing job. Our cat is a little salty and can be difficult and she has been wonderful with him!”

Lauren L.

“We cannot recommend Laura enough! She took such wonderful care of our cat, Phineas, while we were away. Laura is incredibly kind, caring, and trustworthy, and it was obvious from the start that she truly loves the animals she cares for. She kept us updated with pictures and messages throughout our trip, which gave us so much peace of mind. We came home to a happy, relaxed, well-loved cat, and that means everything to us. We will absolutely be booking with her again!”

Kara K.

“Maria did an excellent job with two very hard headed dogs! We appreciated her very much!”

Raeandrea M.

About: We work from home full-time, which means your pup will get lots of supervision, attention, companionship, and cuddles throughout the day instead of being left alone for long periods. Dogs staying with us typically get up to two walks a day, usually 1–2.5 mile walks at nearby trails. If your pup enjoys walks and adventures, they’re welcome to join! We also make sure dogs have plenty of supervised playtime, enrichment, rest, and individualized attention depending on their personality and energy level. We genuinely love pets and try to make them feel like part of the family while they’re here. Whether your dog is playful, cuddly, shy, energetic, or prefers a calmer environment, we do our best to adapt to their needs and routine. We're also happy to provide regular updates, photos, and videos so you can feel comfortable while you’re away. We know how important it is to trust the person caring for your pet, and we aim to create a safe, loving environment where both you and your pup feel comfortable. I have a flexible schedule to give your pets the love and attention they deserve! I take my dog on walks twice a day for 1-2.5 miles in the park and typically spend the rest of the day at home, treating your babies like my own. I have a fenced yard and live walking distance from a park with wooded trails. I have a friendly pup in my home who loves having friends to play with. I will care for your pets like my own!

“Joseph does a fantastic job with our pups when we are away. The are happy and relaxed when we get home, and communication is great . Thanks Joseph !”

Diane G.

“Naomi was perfect! Very open communication and cared for my pups like they were her own! 10/10”

Matthew B.

About: Hi! I’m a reliable and responsive pet lover offering drop-in visits and dog walks tailored to your pet’s routine and personality. I am a current dog owner myself and will take care of your pet like my own. My schedule is very flexible. I prefer to work between 8 and 5 to fit into my family life flow but I am always open to discussion if that doesn't work for your pup. Whether your dog needs exercise, companionship, feeding or potty breaks or just a little attention while you're away, I'll make sure they are well cared for and happy in the comfort of their own home.

“I could tell how much Isabella loves animals and was completely confident that she would take the very best care of my baby girl. Willow was in good hands and I will definitely book Isabella again.”

Patti W.

“Kristen did a great job for us. We contacted her at the last moment, she came to our house without a pre-booking visit, and our dog adjusted very quickly to her without ever meeting her. Kristen was punctual and followed our instructions. Overall, a great experience with Kristen.”

William C.

“Casey was great watching my two cats while I was gone for over a week! Very easy communication and she sent me so many photos which was great for my peace of mind. My cats warmed up to her so quickly and the photos she was sending me cuddling with the boys made me know my cats were well taken care of while I was away. I’d recommend Casey to anyone looking for someone to watch their pet while they are away, thanks Casey!”

Margot D.

About: I’m 21 years old and have grown up around animals my entire life. I have hands on experience caring for a wide range of pets, especially dogs of all sizes and breeds. I’ve had dogs my whole life from Chihuahuas and Dachshunds to Pit Bulls and Belgian Shepherds so I’m comfortable with everything from small, high energy pups to large, working breeds. I still care for my childhood Dachshund and currently have a Belgian Shepherd, which has given me strong experience with daily routines, training basics, exercise needs, and attentive care. I treat every pet as if they were my own and focus on keeping them safe, comfortable, and happy while their owners are away. Pet care is my full time job, so it’s fully built into my daily and weekly routine. This allows me to dedicate my time and attention to each pet’s individual needs, whether that’s walks, feedings, playtime, medications, or just extra companionship. Since this is what I do every day, I have a flexible schedule and plenty of availability to provide reliable, consistent care and give your pets the attention they deserve. I prioritize safety, trust, and comfort in both my home and my clients’ homes. I carefully follow all instructions, maintain clean environments, secure doors and gates, and closely monitor pets to ensure they feel safe, relaxed, and well cared for at all times.

“Lindsey was great about communicating, agreed to set up a meet and greet and had good availability for that, and took good care of our kitty while we were gone. She was able to handle giving a pill. Thanks, Lindsey!”

Sarah M.

“I recently moved from NY to KY and was in need of someone to help care for my four dogs. I had spoken to many people and wasn’t comfortable with anyone as I had my prior dog walker in Ny for over 10 years. I found Tanika and she and I hit it off right away: she was super accommodating to my ever changing schedule. I was nervous to have my one rescue dog meet anyone because he could be unpredictable. Tanika came armed with treats and was relaxed and so easy going with all the dogs that he took to her first!!!! Tanika had been above and beyond amazing . She helps with my dogs that have medical issues and she is always there when and if I need her. She takes care of my dogs as if they were her own and I’ve never had to worry about them when I’m away. She is an absolute god send and I highly recommend her!”

Kimberleigh M.

About: With 11+ years in hospitality, I’m all about attentive, reliable care and that extends to dogs. I follow routines, communicate clearly, and make sure every pup feels safe, loved, and understood. Your dog’s comfort is my priority, and you’ll always know how they’re doing while you’re away. My schedule is very flexible, and I’m able to accommodate most requests. I work in hospitality, so I’m used to managing time, staying organized, and being available when people need me. I’m typically free for drop‑ins, walks, and sitting throughout the week, including mornings, afternoons, and evenings. If you need early morning care, late night check‑ins, or a specific routine for your dog, I’m happy to work around that. Just let me know what your pup is used to, and I’ll match their schedule so they stay comfortable and consistent. Your dog’s safety is my top priority. I’m detail oriented, calm under pressure, and I follow instructions exactly as they’re given. I take the time to understand each dog’s routine, comfort level, and any special needs so they always feel secure and supported. I never take risks with pets leashes stay on during walks, doors and gates are double checked, and I keep a close eye on behavior and energy levels. I’m also mindful of your home and privacy, treating your space with the same respect I give to your dog. You can expect clear communication, honest updates, and full transparency. My goal is for you to feel completely confident that your dog is safe, cared for, and in good hands every moment they’re with me.

“Tyler was on time and courteous. Both Boone and Ava loved him and he sent lots of photos and video updates. We would love to have Tyler back in the future!”

Rachael & Jacob C.

“Chay is responsive, responsible and timely. Would recommend her for anyone looking for an attentive sitter. We were especially impressed by the amazing pictures we received of Huck each visit.”

Tyler W.

“Lindsey always sends me the best pictures of my babies which is a really nice touch that i appreciate when I'm gone! I can tell she spends time with them and is thorough in her visits! She is flexible and has been a lifesaver! I know my pets are safe, healthy, and happy with her! I was admitted to the hospital unexpectedly and with very little notice she agreed to get all their needs taken care of while I was away. Thank you!!!”

Caitlin D.

“Very knowledgeable and thorough. My cat was very unimpressed when we got home, simply because she was very relaxed and at peace being taken care of by T.J.”

Michelle G.