Dog Sitting Winchester
Book a Winchester dog sitter to watch your dog in your sitter’s home or yours.

Over 290 pet parents in Winchester have booked dog sitting
Winchester, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Angelina was fantastic! She took great care of my kitty while I was away and sent regular, detailed updates and pictures. Definitely provided a lot of peace of mind knowing my cat was in good hands.”


About: I work full time at Shenandoah University and am joining Rover to formalize my side hustle, which Ive largely managed through word of mouth thus far. I’ve lived with dogs for about 25 of my 30 years of life - mostly hounds (most recently 2 bassets). And I’ve watched dogs of all sizes, the smallest being a chihuahua mix and the largest a Great Dane. Over the last 5 years or so, I’ve dog sat for friends, family, and connections in the Winchester area. All animals are different and I respect you, their owner, to tell me what’s best for your furry friend. I also will be transparent and over communicate with you so we both can be confident your animals have everything they need. I’m comfortable dispensing medication - including to the really picky ones (I can take a pill/pill pocket and sculpt it pretty much exactly the same shape and size as any mainstream kibble brand). I have experience with puppies and with our senior citizens, who both just need a little extra care and attention. I feel comfortable listening to animals and getting to know their personalities, which are all so different yet equally endearing. If they are trying to say something, though, I feel pretty confident I will notice it - especially after we’ve spent a few hours together. And, if they’re trying to say something and I don’t understand? I’ll reach out just to make sure. I just really, really love animals. I most often watch dogs but have also cared for cats, lizards, bunnies, chickens, and horses (although horses were largely just feeding and brushing/attention). I also have a rescue cat of my own, Luna, who has made me certain I’m equally a dog person AND a cat person. I work 9-5 M-F, and occasionally am tied up on weekends with happenings on campus. I can take an hour lunch (and flex a bit beyond if necessary) to visit the animals for attention and potty breaks. I am single, sober, and genuinely grateful for the work and the company. Animals have so much love to give, and i try to reciprocate that love indiscriminately. Thanks for your consideration and please let me know if I can answer any questions, hop on a zoom call, or speak to any specific needs you find important. No request is too small and I’m grateful for any and all details I can use to keep your animals feeling secure, loved, and cared for in your absence. I work full time at Shenandoah University as an Administrative Assistant in the Office of Global Engagement. My role is in-person on the main campus in Winchester. My routine hours are 9-5 with an hour lunch around 12 or 1. But, there’s a lot of flexibility, especially over the summer when the students are back home. My team is small and I am able to shift my hours when I communicate with them in advance (I.e. I’ll take 2 hours midday but clock in at 8, etc). Outside of work, my schedule largely centers around community and service work. I’m really involved with the recovery community and attend several meetings and events a week, although I can be flexible there too. Most days I’m up no later than 7 am and asleep by 11. But all these things can flex, depending on your and your pets needs. I live alone with a stray-turned-adopted cat named Luna. My place has a small fenced area in the back, enough room for a pup to potty but not much more. But I’m also about a half a mile from Jim Barnett Park and I love their walking trails and their dog park. I’d prefer to house sit at your house, but I’m open to certain scenarios if I can ensure your animal is comfortable in my space. Let’s talk about the details!
About: I have had dogs all my life, and other small animals. I currently have a Treeing Walker Coonhound and 2 cats. I've worked at a cat boarding facility and have pet sat many times over the years, and am confident I can provide skilled and loving care to your pets.

About: I have a love and understanding for all animals! I have trained my own and have learned so much through them. I have a lot of experience with dogs with behavioral issues. I am a college student with a lot of free time. My evenings are free and I have a lot of gaps during the day! I would love to get out on walks with dogs in my gaps. I have my own dog to keep yours company if that is something you would like. If not, he can stay with his other mama when your pup is over! Dogs will get full exercise and enrichment when staying with me. We will be in a fenced in yard running around and go on serval walks throughout the day.
About: I have been taking care of dogs and cats since high school! I am comfortable and familiar with multiple pets at once and even some more eclectic animals like reptiles (turtles and snakes). I would only be able to come to your house to pet sit or walk, I would not be able to bring pets to my apt. I would only be able to pet sit in your home as I live in an apartment where I am unable to bring animals into my space.
About: Hi my name is Jose Alfredo and I can be very laid back and socially outgoing with a fun and friendly personality! I love being around friendly pets and I was a previous cat owner for 4 years. I also used to share my place with my close friend and his dog of 3 years who I helped care for many times. I have other family members and friends who have pets as well and I have been around them long enough to love and know me. I have spent a lot of time around other people's dogs most of my life and have great experience with both dogs and cats. Being around other people's pets over time has given me the opportunity to know and understand different dog and cat personalities and each ones individually unique needs and traits. Book me and I will walk your dog, feed it, play with it and make sure it has gone to the bathroom. I will tend to your cats' need as well and make sure it's fed, hydrated and help maintain it's litterbox's cleaniliness and given lots of attention! I am also willing to help with small house chores like taking out the trash, bringing the bin to the front, watering your plants or any other simple house duties for no extra charge! At the moment I will go to you to take care of your pet in your home so you don't have to worry about putting your pet in a new environment it's not used to. I will make sure everything in your home is as tidy as before I even arrived. As long as you can provide me with the proper details and instructions about your pets' needs, where things are and how to get in and out of the house, then I promise you everything will be done as requested. As a way of building trust, we will arrange to do a proper meet and greet at your home or a public place like the park. This is so me and your pet can get familiar with each other, earn trust between owner and sitter, and have comfortability and assurance that your pet and home will be in good hands. Thank you for choosing me to care for your pets! I am currently flexible with availability for most days of the week as I do not have any other full time job at the moment. However, I currently am a student studying full-time and sometimes get involved in campus events, extracurriculars, and other student organizations. So Tuesdays and Thursdays I'm typically more busy with classes. But as long as the requested time works around my schedule and classes then we can make it work and I can be available whenever I am not spending time on campus. I do prefer to be notified at least 3 days in advance for requests but I am also willing to take up to same day bookings as long as I am completely free for that day, but it is not guaranteed. But please do try to reach out and book with me in advance at first if possible. I also prefer to schedule a meet and greet prior to accepting booking requests for new first time clients. But I will be more than happy to work with you so I can make a new furry friend if we are a great fit for each other! I used to play with my roommate's dog every day and feed him or take him outside to potty when the roommate was not around or unable to. I play ball with his dog, tug of war and give him belly rubs. His dog is also very attached to me as I am to him. I also was a cat owner for 4 years who I took care of every day from feeding him to ckesning his litterbox and playing with him. I hope to form this same kind of relationship with your pet!
About: I’ve been dog and cat sitting since elementary school, starting with walking my cousins' dogs and caring for them while they were away. I also have extensive experience with feline care, spent hours socializing with friends' cats, and dropped in to feed them when owners were out of town. I work from home and set my own schedule so I’m available for dog walks and cat drop-ins every day of the week from morning through afternoon. When caring for pets I like to follow exact instructions for feeding, potty breaks, and playtime since all pets have their own quirks. I always ensure the home is secure, clean, and locked up before I leave.
About: I will provide the best pet care possible ! Your furry family member will be loved and cared for just as you wish! I grew up with so many pets and now am a proud owner of a pup, names oso, as he’s no longer a puppy he will always be treated like one just as our children even all grown up will be our little girls and boys always so are our furry family memebers ! I’m great at tug o war, playing fetch, or just taking a stroll around the neighborhood! I have a very flexible schedule and a great direction follower ! You just let me know what needs your pets require and they will be completely successfully! Thank you hope to hear from your soon I have a full time job but can come before and after. I provide feeding, fresh water, litter box cleaning, playtime, medication administration (if needed), and plenty of updates with photos so you can have peace of mind while you’re away I take the time to earn their trust and follow their routine.I do have a cat and dog, so my house onboarding is available on weekends only.
“I am so thankful for Sarah! My maltese senior is best described as "high maintenance". I had a long day out of the house and was super worried about him being alone. Sarah came for a visit, gave him his strawberries and Pup Cup, spent some time with him and sent me a photo. <3 When I got home that evening, I found him contently sleeping on his blanket. Exactly as I had hoped!”

“We had a family emergency and had to leave our Dog Piff at home and Shaghayegh was amazing! She really went above and beyond for my family and made sure our dog was taken care off. She let us know before and after she left and always sent pictures everyday! I would 100% use her again!”

About: Hello, pet parents! My name is Jessica, and I bring over 25 years of dedicated experience working with both dogs and cats. As a professional dog groomer for the past 15 years, I have developed a keen eye for pet care and well-being. At home, I share my life with a delightful trio: a standard poodle, a lovable pit bull, and a majestic Maine coon cat. Each of them has taught me unique lessons in care, patience, and the joy of pet companionship. Why choose me? • Decades of Experience: With 25 years of hands-on experience, your pets are in knowledgeable and capable hands. • Groomer’s Expertise: My grooming background ensures your dog not only gets a great walk but also some extra TLC, including coat checks and paw care. • Personalized Care: I understand that every pet is unique. I tailor my services to meet the specific needs and personalities of each furry friend. • Safety First: Your pet’s safety is my top priority. I am trained to handle various breeds and temperaments with care and professionalism. Let me provide your pets with the exercise, attention, and love they deserve. Book a walk today and see the difference an experienced and passionate pet professional can make! I’m a professional dog groomer with a flexible schedule that allows me to provide dog walks and drop-in visits throughout the week. I enjoy using my available time to give pets the exercise, attention, and dependable care they need while their families are away. Your pet’s safety and comfort are my priority. With 25+ years of experience caring for dogs and cats and 15 years as a professional dog groomer, I’m comfortable working with pets of many breeds, sizes, ages, and personalities. During drop-in visits, I can provide potty breaks, feeding, fresh water, playtime, and medications as directed. I also offer dog walks tailored to your pet’s individual needs.
About: We provide a special touch of walks, wags and worry free pet sitting! From zoomies to cuddles we can match your fur babies energy level. Apple Pay,Venmo,Cash or in app payments welcome. We’re a meticulously organized couple which permits us a flexible schedule when caring for our fur babies. We’d love to extend the care to your fur babies as well! We recognize that each pet has their distinct personality and we like to honor that. Pelusa, our oldest cat, despite her age, carries a playful kitten soul so we like to dedicate extra stimulating play for her. Our youngest he likes to exert his energy by bird watching and running and jumping around so we’ve accommodated the house for his races since playing 1 on 1 with him does not captivate his curiosity. Just like that we can confidently say we love learning about our clients and their pets personality so we can make the best transition when caring for them that day and so everyone feels seen and included, even the little ones! We also understand pets can be very oriented to habits so we like to know what habits and/or rules you have for your pets so we can respect and abide to those as well!
About: I’ve been volunteering at my local animal shelter for the past two years, where I’ve had the opportunity to work with dogs and cats of all ages, sizes, and personalities. This experience has taught me how to recognize different temperaments, build trust with shy or anxious animals, and confidently care for energetic pets as well. I genuinely enjoy getting to know each pet’s unique personality and always strive to make them feel safe, comfortable, and loved while they’re in my care. I’m a PA (Physician Assistant) student who absolutely loves animals and enjoys spending my free time caring for pets. My class schedule keeps me busy during the day on weekdays, but I’m available for early morning (before 7am) and evening visits (after 5pm) on weekdays, open on weekends, and many overnight stays. Your pet’s safety, comfort, and routine are my top priorities. I know that every pet is different, so I take the time to learn about their personality, preferences, and any special needs before each booking. I carefully follow all feeding schedules, medication instructions, exercise routines, and house rules to help them feel comfortable and maintain their normal routine.
About: I took care of my neighbors dogs while she was away. I've house sat before and I enjoy long and or short walks with any dog! I'm home from school for the summer so I have plenty of free time to walk and over house sit! I'm free in the mornings and afternoon, 7 days a week. I can walk your dog as far as you would like and will spend as much time with your dog as necessary! I enjoy staying active and don't mind taking your dog for runs as well! For cats I love being with them and keeping them company, while feeding and providing clean up.
About: Hey there my name is Allison and I am a huge animal lover! I will love on your fur babies while you are gone and make sure they have what they need! As someone that has every pet but a dog of her own and has always wanted one, I will completely take advantage of the time I get with yours! I am comfortable with whatever is in need feeding, walks, backyard play, even just hanging out at the house and keeping your animal company! I have experience with a wide range of animals and I will make sure your needs are met! I am so excited and looking forward to meeting you and your sweet fur baby! Whatever animal comes my way I will make sure they are taken care of!

About: (Formerly Kamp Kelley) I have been fostering small dogs for a rescue group in No. VA. for the last 9 years (my aching back doesn’t allow me to work with dogs larger than 20 lbs)--prior to that I fostered cats and kittens. I has experience with many types of small dogs—especially Shih Tzu’s and Llasa Apso’s, but also Yorkshire Terriers, Basset Hounds, Pom's, Toy Poodles, etc. My expertise is in rescuing and caring for senior and special need dogs. Since I have a dog-friendly house and a large-fenced yard (1/4 acre) for them to run and play in, I decided to become a dog-sitter 5 years ago. I believe in loving and treating your fur-baby like my own! We keep her home and yard dog proof so your little angel will be in a safe, relaxed, dog-friendly, and loving environment! Because I am retired, my schedule is very flexible. I'm retired and except for occasional trips to the store, bi-weekly Bridge games. monthly book group and a occasional meeting, I'm home ALL THE TIME. At this point, I am accepting only ONE dog at a time EXCEPT if there are 2 dogs from the same household. Same for cats. I have a large, fenced yard that can be separated off. I have lots of dog equipment. For example large crates if your dog is used to being crated, bowls, beds and cushions, a big bed for them to share with me, jackets, leashes, kongs and lots of love and affection. Same for cats--EXCEPT, I let them out only on the back deck (enclosed).
About: I’ve been lucky to spend the past 7 years caring for both dogs 🐶 and cats 🐱 of all ages. I’ve looked after pets at every stage of life — from 2-week-old kittens needing bottle-feeding to senior dogs and cats who required medication and gentle support. I do my best to understand each pet’s unique personality and needs, and I care for them with patience, kindness, and genuine love ❤️ I’m available for daily care from 6am to 6pm, and I also offer overnight or weekly boarding depending on your needs. If you have a special schedule in mind, feel free to reach out. I’ll do my best to make it work for you and your pet. I live in a quiet and spacious home with my husband and four sweet pets. We have three gentle cats 🐱 and one senior dog 🐶 who has been part of our family for over a decade. Pets who stay with us can move freely around the main floor and relax in a cozy upstairs room made just for them. There are soft beds, toys, and even a little cat wall they can climb and explore. Our neighborhood is peaceful and safe, with two small parks nearby where we can enjoy slow, sniff-filled walks or just spend time in the fresh air together 🐾 Whether your pet is outgoing or shy, full of energy or in their golden years, I always do my best to help them feel safe, comfortable, and truly cared for, just like home.
About: I have eight years of experience caring for cats. I absolutely adore cats, and having had a cat of my own for almost 10 years now, I know how beloved and valued they are by the families I help. Throughout my years of cat sitting, I have cared for cats of all ages, administered medications, cleaned multiple litter boxes, and, of course, entertained with cat toys! Your need for pet care is never a burden. I take true joy in having the opportunity to meet and care for new furry friends! I currently work as a fitness specialist and personal trainer in medical fitness, so I have full availability on the weekends and my schedule with training clients largely allows me to check-in on pets throughout the day. I am unable to keep cats in my home; however, I am happy to travel to clients' homes and stay overnight to provide care. In my previous experiences cat sitting, I often check-in multiple times daily throughout my work day and stay in the home each night. I provide drop-in or house-sitting services.

“Erin was super helpful looking after my cat Mittens. I had a seamless experience introducing her to Mittens and had confidence that her drop in would go off without a hitch. She was very responsive, friendly, and a pleasure to work with. I look forward to having her as my go to sitter in the future!”
The median cost per visit for dog sitting in Winchester is $20
Dog parents share their Rover experiences - Winchester
From our very first meeting, I could tell Alex was completely comfortable with our big, overly excited boy. Franky loves his walks and having someone to spend time with, and I really feel like Alex is going to be a wonderful friend and walking buddy for him. 🐾❤️

I am very happy with Christa! She did an amazing job with my pups. Bo and Sheena are very happy too. This was my first time using this service and I’m so happy that I found Christa. It’s not easy for me to leave my pups with anyone. Thank you Christa for being so kind and friendly to my pups. I will definitely be using these services again and request for Christa.

Karen was great! We had a trip planned and Whiskey had been sick since November. Thought he would get better but still had a lingeri g cough. We had another sitter lined up who had their own dog and we didn't want that dog to get sick too. I found Karen last minute to come to our home and take care of Whiskey with dropins. She did such a great job and kept us informed on his coughing. Thank you so much!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your 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.
Meet local sitters who will treat your dogs like family

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Popular requests for dog sitting - Winchester
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winchester average 6 repeat dog sitting clients
FAQs for Dog Sitting - Winchester
Frequently asked questions about Rover
The average cost for Dog Sitting in Winchester on Rover is $22.2 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .
As of September 2026, there are 844 sitters on Rover offering Dog Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winchester stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winchester choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Winchester with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Winchester. On Rover:
- 93% of sitters can help with special care needs
- 99% can help with giving oral medications or injections
- 96% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.







