House Sitting in Winchester

“Caring, reliable, and all around perfect sitter for our dogs. We couldn’t be more pleased!”

Jessica P.

“Jessica was awesome she made sure to communicate with me and send me updates of my pup through out the week! Will definitely book with her again!”

Hannah S.

“Lindsey was an excellent house/pet sitter. She provided excellent care and communication the entire time. Will definitely recommend her and book her again. 🙂”

Mickie V.

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!

“Dina was great! Very responsive, send pictures, and updates. Never would have know she was at the house, took great care of everything. Dogs loved her and were happy and healthy when we returned. Such a relief to have her so we could take a weekend off. Highly recommend!”

Katherine J.

“Hannah did an outstanding job watching my dogs at my home for a couple nights. Her communication and updates throughout her stay were outstanding. She went up and beyond to make sure the house was in better shape than when it was left. My dog’s really enjoyed her. I would definitely recommend Hannah.”

Scott D.

“Excellent! Terry was very considerate of our home and extremely accommodating with the small details and requests. Communicated regularly with text and photos. Most importantly our kids loved him. If you're looking for a house sitter you need look no further.”

Randall D.

“Amazing!!! We booked last minute and Melissa was so responsive, so attentive and loved on our baby like she was her own! I can not recommend her enough!”

Sheel S.

“Misty was great and Luna was safe and secure, happy and healthy when I arrived home. Finding a dog sitter on Memorial Day seemed like an impossible request so imagine my surprise when she accepted, arrived and did a great job. I highly recommend her!”

Scott Z.

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.

“I cannot say enough positive things about Mary Grace! She house sat/pet sat our cat Luna and was fantastic. She provided great updates and photos and was attentive to all details house/pet related. She left our place cleaner than when she came and was very flexible when we had a slight schedule change. We’ll definitely be using her again!”

Lisa K.

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.

“Sara was excellent and was able to accommodate all of Kylo's needs and provided plenty of updates to give us peace of mind that our dog was in great hands. Sara also went above and beyond in taking care of our home and left it just as is was when we left!”

Isaac P.

“Sloane was so good to our babies while we were out of town. She was respect and communicative! Would use her again in a heartbeat!”

Mollie K.

About: Ready for tail wags and endless fun! Having raised my own pups for over a decade, I’ve experienced it all—from the wild puppy phases to the sweet senior years. I know exactly how to keep animals engaged, safe, and thoroughly entertained. Your dog will get all the playtime, attention, and expert care they deserve! Pet care fits seamlessly into my daily routine because my schedule is highly flexible! Whether I am hanging out with cats or walking dogs, my open availability allows me to easily match your pet's established routine. I can accommodate early morning feedings, mid-day potty breaks, high-energy afternoon play, or late-night cuddles. Because I am so adaptable, I can quickly adjust to whatever timeline your pets need to stay happy, comfortable, and stress-free Whether at my home or yours, I focus on safety and mimicking your pet's normal routine. In your home, I strictly follow your rules, keep litter boxes pristine, walk dogs on their usual routes, and secure your property. In my home, I provide a fully pet-proofed, welcoming environment where cats and dogs get dedicated attention, structured playtime, and their own safe spaces to rest comfortably.

“Brian was great! He communicated well, took great care of both our dog and cat (and the dog involved giving pills regularly!) - it was great to be able to away for a weekend and trust that everything was in good hands at home!”

Beth S.

“Thank you so much for taking such good care of Creed and Celina!!”

Lisa Y.

“Casey was very sweet and polite. She took excellent care of all my boys. She kept in touch and sent pictures. I would definitely hire her again!”

Jennifer C.

About: Hi, I’m Aidan! I’m a Lexington-based dog sitter and walker with hands-on experience caring for large, active dogs, especially Labradors. I currently have two labs of my own and have had dogs my entire life, so I understand the importance of exercise, structure, patience, and affection. I specialize in dog walking, drop-in visits, and house sitting in your pet’s home, which helps dogs stay comfortable in their familiar environment and routine. I’m especially great with: • Large and high-energy breeds • Dogs that need real exercise, not just a quick potty break • Puppies needing routine and consistency • Multi-dog households • Dogs that thrive on play, fetch, and mental stimulation I prioritize communication and always send photo updates so you know your dog is safe, happy, and getting the attention they deserve. My goal is to make your pet feel comfortable and cared for while giving you complete peace of mind. I currently work part time, which gives me a flexible schedule and strong availability for walks, drop-ins, and house sitting throughout the week. I live a highly active lifestyle and regularly take my own dogs on walks and runs, so I’m a great fit for pets that need real exercise, play, and attention. I prioritize keeping pets comfortable and safe in their own home environment by sticking closely to their normal routine, feeding schedule, and exercise needs. During walks and drop-ins, I’m very attentive with leash security, doors, gates, and surroundings to make sure your dog stays safe at all times. I’m experienced with large and high-energy dogs, so I’m confident handling strong pullers, excited dogs, and multi-dog households. I always follow any house rules, crate routines, medication instructions, or specific care requests exactly as provided. I also send regular photo updates so you can feel confident your pet is happy, safe, and well cared for while you’re away.

About: I’ve grown up around pets and have experience caring for both dogs and cats, including feeding, walks, playtime, cleaning up after them, and making sure they feel safe and comfortable. I’m patient, dependable, and genuinely enjoy spending time with animals and learning their personalities. I currently have a very flexible schedule and plenty of availability throughout the week. I’ll also be starting DoorDash soon, which gives me the ability to plan my hours around pet care and stay reliable for bookings. Your pet’s safety and comfort are my top priorities. I’ll always follow care instructions closely, keep pets secure on walks and during visits, provide updates when needed, and make sure they feel calm, cared for, and comfortable in my care.