House Sitting in Winchester
Find a loving dog sitter to watch your dog overnight in your home.

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winchester house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Katherine did a great job with our 2 rambunctious dogs! She was very communicative during her stay which made us feel very comfortable. I would definitely have Katherine stay with our dogs again”


About: I have 4 dogs of my own and have pet sit once when I was 13. I love dogs and would love to care for you furry friend. I can travel far but wouldn't like to drive more than 45 mins. I currently do not have a job so I have plenty of time and availability to take care of your furry friends,I am mostly interested in dogs because I'm am allergic to cats. I make sure they have fresh water each day,if its hot out twice a day,I have a dog named Ellie which I could bring if you didn't care or if you wanted your pup to have a friend to play with as I clean and make sure everything is perfect.
“April is truly a dog whisperer! She watched my two Yorkies at my home, and I couldn't be more impressed. One of my dogs, Dawson, has severe separation anxiety and usually takes a long time to trust strangers. To my total shock, it was love at first sight for him—he didn't even care when I left! April took wonderful care of my fur babies and even went above and beyond by leaving my house spotless. Finding someone Dawson trusts is rare, and I’ll definitely be booking April again.”

About: Reliable dog care from a boarding kennel worker with hands-on experience in daily care, routines, and behavior. Beginning AKC training soon. With some veterinary experience as well. I have a flexible schedule as a full-time student, so I can stop by before or after classes for walks, feeding, medications, bathroom breaks, and other care needs. I’m happy to help with weekend visits and can do overnight stays when possible. I’m comfortable traveling up to about 25 miles for pet care. I treat every pet like part of my family, giving plenty of attention, love, and consistency. Inside my home, I maintain a clean, safe, and comfortable environment, following each pet’s routine for meals, bathroom breaks, play, and rest. I’m attentive to behavior, health, and individual needs, and I make sure pets feel secure, happy, and cared for while their owners are away. My reliability, patience, and flexibility help me provide personalized care that puts both pets and owners at ease.
About: Hello, my name is Jordan. I am a pet sitter based in Mount Orab, Ohio! I have 4 cats and a little Chiweenie Puggle with my boyfriend. I often take care of strays around the neighborhood and have even taken in a few. I work to advocate for those who don't have a voice. I enjoy walking in the outdoors! Perfect for your little pup full of energy. I have always had a passion for animals since I was little, accumulating a lot of pet care experience under my belt with smaller animals over the course of a decade. I always treat every furbaby as if they are my own. I cannot wait to meet yours, they will have my full heart and attention! Always up to answer those questions and concerns, you can rely on me to be there for you and your dog. I tend to specialize in small dogs and other small animals. I have a fairly flexible schedule due to working for myself currently, making plenty of time for your pet throughout the week Monday through Sunday as well as most holidays! I care for the pets in and around my home by feeding with set schedules, cleaning up any messes created, scooping litterboxes everyday, cleaning food bowls, walking my dog multiple times throughout the day, crating my dog at night, as well as keeping them enriched and entertained!
About: I have been around animals my whole life. I currently have 2 dogs and 3 cats but have also had reptiles as well. Animals are something I throughly enjoy being around and caring for. You can be assured that your animals will recieve the care and affection they need and deserve if you decide to book me for your pet sitting needs! I work full time 3rd shift so am available mostly during the day. Most weeks I work 4 days Monday through Thursday. With enough notice I can be available anytime. I provide a fun and safe environment for all of the animals I care for. I’m not in this app to just come to your house and provide basic needs (unless of course that’s all they need) . You can insure that your animals will get lots of affection and care. This app is a hobby for me and I do it because I love animals and enjoy helping others.
About: I intern at an animal sanctuary where I provide full animal care to cats, dogs, foxes, birds, wolves, horses, a beaver, a bear, an elk, and much more. I have been there for over a year as well as taken care of many other animals for families over night and daily check ins. I am studying environmental science where I hope to work with animals so I have been gaining a lot of experience and knowledge with all kinds. I work another job currently as well as school so my check ins would be early morning and nights. My schedule varies from day to day so I’m willing to work it out as needed. I am available for over nights almost every night. I have watched animals with and without fences. I have gained a lot of experience in how to keep both me and the animals safe from my internship knowledge.
About: I am a animal lover of all sorts, I have two healthy dogs that make my days better. I have cared for dogs for 7+ years. I always watch my family members pups when they have to go out of town. I someday would like to be a vet I will be going to school to pursue that. I take very well care of my pets and I hope you consider me to take care do your furry four legged best friends/fur babies. I will do my best to love and care for them like they are my own. I have cared for senior dogs 12+ I have cared for hyper dogs, mellow dogs, special needs dogs. Dogs of every shape and size make me happy. I have a pretty open schedule open to different availability. Currently work night shift but will work varying shifts with different levels of time and days. But will always find a way 🙂 I love my pets and don’t restrict them that much, love to take them on walks and play with them we love cuddling on the couch. I would take care of any and everybody’s pet like my own.
“This is our second stay with Allie and we always love having her! We had a long trip out of state this time and it was nice to be able to leave our pups and home to someone we can trust. She’s a great communicator, polite, considerate, and great with our dogs. We’ll keep having her back as long as she’ll have us!”

“Julie was so helpful to us! She took care of our elderly dog and skittish kitty with as much love as we would have. She provided regular updates and photos and even did light housekeeping for us-that we didn’t expect at all!! I highly recommend Julie for your pets and home.”

About: Woof! Im a responsible and trustworthy military veteran with a true passion for dogs.I have ample experience, having helped run a nonprofit dog rescue for many years. I’m kind, gentle, patient, and extremely comfortable around canines. Being an active and energetic kind of gal, your babies will have a blast during their time with me! Their paws will be in good hands. P.S ( I’ll treat your dog as if they were my own). I work from home, (free lance writing) and have plenty of time to host your dog. Being a homebody, I only step out for a few hours, for kickboxing and weight training. I have an extremely large yard with lots of room for: exercise, playtime, and exploring. And I’m well equipped with several doggy condos (crates and cages).
About: As your pet's second best friend, I offer tailored care, genuine love, and a paw-sitively unforgettable experience! I am well educated in dog training, ensuring they’re mentally and physically stimulated, to overall pet health. I take care of my dog to the fullest extent, your dog will be treated all the same as a new member of the pack! To ensure safety and health, we don’t play right after eating to avoid bloat, I am very conscious of heat on their paws when walking on different surfaces, I avoid rawhide treats and go with homemade or very natural treats instead, and those are just scratching the surface of do’s and don’ts! I keep a structured but flexible routine, which allows me to give your dog plenty of attention, exercise, and consistency. I prioritize walks, potty breaks throughout the day, and lots of playtime and enrichment. I’m home often and very intentional about making pets feel safe, comfortable, and cared for. Whether your dog needs structure, cuddles, or high energy engagement, I adapt to their personality and routine to make their stay feel as close to home as possible! Your dog’s safety and comfort are my top priorities. I have a well-socialized dog, Dilo, who has a background in working in high stress environments to not be reactive. Nonetheless, I always do slow introductions to ensure everyone feels safe and comfortable. If needed, I can crate or provide separate spaces for rest and decompression. Inside my home, I maintain a clean, structured environment with plenty of space for play and relaxation. I closely monitor interactions, follow feeding instructions carefully, and stick to your dog’s routine as closely as possible so they maintain some sense of routine while being away from home.
“Katie is an incredible petsitter!!! She managed taking care of my 3 pets, including one who goes to daycare 3 times a week. My husband and I went on a week-long vacation and I didn’t have to worry about our pets or home a single time. Katie sent me daily updates, which was awesome, and took the time to meet with us beforehand. Seriously can’t recommend her enough!”

About: I have been around animals all my life. I was taught to carefully care and love fur babies at a very young age. My wide variety of pets over the years has led me to obtain vast experience and carefully handle challenging situations. I am currently full time employee. I am available at any time during the weekend but will need a 3 day advanced notice for any care. I had 2 pets inside my childhood home. I used to take them out consistently throughout the day. Additionally I had a Great Dane at my childhood home and she was solely outside. My 2 pets inside were small poodle mixes. They would eat play and sleep inside on my bed. I recently moved from California to South Carolina and I have no pets with me now.
About: i have taken care of some sort of animal since i can remember. My first best friend was Danger, a beautiful Pit Bull i potty and command trained at 5 years old. Since Danger i have raised a variety of dogs (big and small), cats (various breeds), my birds (Vickie and Victoria), one turtle, several fish, etc. My longest lived relative was Chewie (small dog) who recently passed away nearly making it to 20 years old! I am in the process of learning food and natural remedies that can extend the lives of dogs and cats as i truly love animals more than most people. Even having a few terrifying memories with animals, i still hold true to the fact no animal is ever evil or wicked, like some humans. If an animal is mean, it has a reason to be such a way, and all it needs to heal and become clean is a little Jesus love to let the small critter know, “You are appreciated.” This mantra and mindset has taken me very far in life, and enables me to be your Pet’s Next Best Friend! Don’t worry, Dogs are happy! Pets are my passion! i ensure you we provide everything your pet needs under one woof! Who is we? Me myself & i, i like big mutts and i cannot lie, but i love the pitter patter of tiny paws too! i know, i know.. “you had me at woof” but i cannot stress enough how pets are my passion. I am the top dog walker & caretaker, and i assure you we will fetch amazing results! Book with us! I double dog dare you! i currently work at a suit shop (Men’s Wearhouse near the Kenwood Mall) selling suits! I am in a transition period of trying to get my first solo dental practice up and running! Those are the two “jobs” which consume my time, but truly i tell you i consider neither real work as i love both as a passion. When i am not doing either of those things i am typically found deep in the Word of God, with my family, or out and about in nature or at a dog park. I have a very wide schedule as i prioritize every second of each day to maximize my time. You ever meet someone and think, “how do you do all that in a single day? Do you have more than 24hrs to work with?” If you have never met someone like this.. hello! Nice to meet you! I am happy to be the first! 🙃 I have the same approach well similar is a better word. My approach for pets in my home is simple. Treat pets as any other honored or distinguished guest. I keep a variety of snacks and treats at home, such as peanut butter, and a variety of other treats like 360 pet care freeze dried snacks, i have a few toys that seem to be popular among cats and dogs, a case of laser pointers, in case one stops working.. hate to be caught without one when the cats especially are having a good time! I try to stay as prepared as possible for any circumstance that may arise. At my clients home i do the same, and i pack a travel bag similar to the one i bring to the dog park when i frequent there. The prime difference between at home and at a clients home is i practice pet care with added, greater attention to detail. Jesus said love your neighbor as yourself, but i tell you (myself) love your neighbor greater than yourself, better than yourself, and you will do well! So with that in mind i try to always think of ways to do more, do better, and be better whenever someone graciously invites me to their home, and whatever i devise i later apply it to myself, so my overall abilities may rise, then i rinse and repeat!
About: Since about 12 years old my neighborhood friends would hire me to dogs sit while their family went out of town. I’ve always had a huge amount of love for animals so I never had any problem doing so. Fast forward 5 years later my parents began breeding French bulldogs. My siblings and I had a lot of responsibility on our hands are far as feeding them, bathing, keeping them groomed, making sure they’re up to date on shots and etc. I currently work from home so that’s enables me with plenty of free time to walk, play with/take to the park, and feed your lovely animals! In my home my dog is crate trained. I do have a crate for my puppy for if friends come over and are not comfortable with him I can put him away for a few hours. I prefer all animals be crate trained , but only go to the crate if they would like to do so. I do not mind dogs walking around my house. I have a puppy of my own so every morning I get up and take my puppy on a 30 minute walk as well as every evening once I get home from work. I have an animal friendly house so I usually let pups/kittys run around the house as long as they’ve been fed and taken out for a potty break.
“John did a great job taking care of my dogs and cat (and plants) while I was out of town. He sent pictures/videos each day and communicated promptly anytime he had to leave my house. Would definitely book again.”

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
House Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Winchester.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winchester house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.


