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

Over 247 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.
“Melissa was such a lifesaver! She helped us super last minute when a previous sitter fell through right before we left for a family reunion, and we couldn’t be more grateful she was there! Super flexible and communicative, Melissa took lots of adorable pictures and left detailed updates of each visit. And she was super sweet with our fur babies and loved on them so much! 100/10, will absolutely recommend and hire for her again! Thank you so so much Melissa!”

About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)
About: What sets me apart from other sitters is my lifelong experience with animals, having grown up with dogs and cats in the country. I provide compassionate care for senior pets. My joyful, hardworking, and caring nature for animals ensures each pet receives the personalized attention and love they deserve. I am a flexible and reliable pet sitter available anytime with advance notice. Ready to provide loving, attentive care for your pets whenever you need! I provide attentive care in my clients' homes. For outdoor time, I use a leash to ensure safety and proper exercise. Your pets will receive personalized attention, love, and regular activity.
About: What sets me apart is the level of attention, patience, and genuine care I give every dog like they’re my own. I understand that every pup has different needs, personalities, and routines, and I take the time to make them feel safe, comfortable, and loved while you’re away. Because I’m home often, I’m able to keep dogs on their normal routines as much as possible, whether that means regular feeding times, medication schedules, exercise, or simply providing a calm and comfortable environment. I enjoy having animals around and make sure they get lots of interaction, affection, and personalized care while their owners are away. When caring for pets in a client’s home, I focus on keeping their routine as normal and stress-free as possible. I follow all care instructions closely, including feeding schedules, walks, medications if needed, playtime, and any specific routines your pet is used to.

“I wanted Day to spend some time with my dogs prior to an extended dog sit. My GSD likes to jump on people who enter the house and gets very excited. Day took charge and let Mira know to get off and waited for her to calm down before proceeding. Both dogs have specific needs ranging from sensitive stomach issues to elderly care issues. Day got to spend time with the dogs while I left them alone to get acquainted. The visit went well. Dogs were snuggled up on the couch with Day upon my return.”

About: NOW OFFERING SERVICES IN CHARLES TOWN, WV AND LEESBURG, VA (and the areas inbetween!) Why trust this stranger? - Degree in animal behavior - Licensed Veterinary Technician (got insulin or methimazole? No problem!) - Experience with high drive breeds and willingness to run them - I love large animals, exotics, cats, dogs, you name it! - Worked full time while in college doing doggie daycare, dog grooming, dog training and pet sitting - Love pictures of your pets while you're away? I love sending them to you to give you peace of mind! I'll treat your fur babies just like my own. - More than willing to work with any and all of your pet's needs - I have a full belief that a tired dog is a good dog! You can expect lots of exercise catered to your dogs' favorite activities, be it biking, swimming, long walks, running or playdates with my own very dog - friendly and energetic terrier! **I REQUIRE A MEET AND GREET PRIOR TO ANY PET CARE- this is for both my safety and that of your pets!!** With my current set work schedule I have reliable availability to care for your fur babies while you are away! I work 4 set days, so there’s little question to when I’ll be able to stop by. The great thing about the services I offer, is that I do my best to adhere to their already set schedule making your time away from them as stress free as it can possibly be.
About: I have had dogs all my life and have always had the responsibilities to look after them. I have been around bigger dogs as well as smaller dogs and very familiar with senior care. I work full time but with a flexible schedule and a husband who works odd hours so I can be very flexible with times and dates! I am willing to travel within reasonable distance to look after your animals with reasonable notice. I do understand last minute things can happen as well.
About: I love animals Have always had an animal in my life. Not sure if I would function without one. Looking forward to caring for other animals. I currently have open availability. Not currently working outside of my home. Looking forward to helping others with their pets and making them feel comfortable being away from them Prefer to care for pets in your home. I have 2 dogs and the are pretty much just used to each other. Need to know what your dogs temperament is likes and dislikes
About: Ever since I can remember, I have grown up with a pet in the house. I have great experience with pets such as: Dog walking, Caretaking, Bathing and loving animals! I have participated in many dog training sessions which has given me experience with potty training puppy’s, proper dog walking and owner caretaking tips. As of right now I am a bunny mom and have learned so much about smaller animals as well (did you know you can come litter train bunnies? Being around pets is a big joy in my life. I love knowing a furry friend needs and almost as much as we need them! Given this, I am a motivated, reliable and trustworthy person especially when it comes to animals. Thank you!

About: Hello! My name is Kaylee, I am 23 years old and my biggest personality trait is my love for animals. If you were to ask someone who knows me, they may say “that girl with the zoo? I currently have 5 pets, who I consider my children, and that is the least amount of animals I have ever owned at once. (Only due to apartment living.) Caring for animals is my comfort and passion, it truly brings me joy. I have never lived a day without pets- and I don’t want to, so, I focused my career around them. However, I’m still in search of more! I am currently a manager at a dog boarding facility part time, and I love my job, but I would love to find more local work. At my facility, I am currently managing multiple groups of up to 20 free ranged dogs at a time. I have worked with nearly every dog breed out there, and I have loved them all. I have experience in handling many medical conditions in dogs, such as anxiety, allergies, seizures, joint issues, diabetes, asthma, and many more. I also have experience in administering a multitude of medications, including inhalers and insulin. I am currently working part time, and my work days are typically the same each week. I am unavailable on my work days during hours 4 AM- 3 PM, but I would love to work with you any other time! The approach I take to care for a pet depends on the pets temperament and needs. As I have probably met over 2,000 dogs at this point- I understand that each dog is different. Some may want constant affection, and I’m more than happy to give that! However, I know that some pets appreciate their space, or need to be taken slowly with.
“This was the second time I’ve had Katie check on my three cats while I was away and just like last time, she was absolutely amazing! She even threw a birthday party for my two girls, who share a birthday on July 4th. I am so beyond grateful to have found a pet sitter that has such a genuine heart for animals and gives the absolute best care. I will absolutely be booking Katie every single time I need someone to check on my babies! You can trust that she will give your pet(s) the best care and love while you are away. Thank you again, Katie! My cats will certainly be happy to see you again (especially Meejum lol)”

“Alexia was the best! Very professional and caring. She watched our (anxious) hound when we were on vacation in Harper’s Ferry. We are from another state, didn’t know the area and didn’t have definite plans until we arrived. Alexia was flexible and understanding. She responded to text quickly and followed all directions. Most importantly our dog loved her! She is a gem. Highly recommend!!”

About: I have been a dog walker for 6 plus years and have my own 4 year old bully mix! I regularly care for another dog as well! I give love as if they are my own and spoil them rotten! I give medications, care for wounds, post surgery care and have done chemo treatment trips and after care! I currently have part time hours at work. I am available mornings, evenings and weekends! I have plenty of extra time and love for all your pets! A nice home with a good sized fenced in yard for lots of play time and sunbathing! I have a very playful and loving pup myself who loves everyone and everything! During the work week our pup is only alone about 4 hrs a day and we do have a camera so we can check in on her. When there is another pup in our home we do keep them separate while no one is home for safety and comfort for all. When home they can all run and play as much as they want! Lots of toys and outdoor time! Supervised meal times as well!

About: If you want your dog to get the best of care with lots of TLC and fun then let me take your dog out while you work or on vacation! Doggie Daycare will provide the highest standard of dog walking and pet vacation services in your home or mine! I will personalize my service to meet your pets needs- days, nights, weekends and holidays! I have been lavishing and loving dogs and cats for over 25 years from Minnesota to Boston to West Virginia! When you can’t be home or need a place for your dogs to stay-give me a call. Daily dog walking-choose between a 20 min. relief walk outdoors or a 1 hour romp! Includes feeding and water check. Your dog deserves this! I am home most days and have a very flexible schedule, allowing me to provide plenty of attention and care to your pets. I’m available for drop-in visits and pet sitting throughout the week and on weekends. Because I spend a lot of time at home, I can accommodate your pet’s routine and make sure they feel comfortable, safe, and loved while you’re away. I treat every pet as if they were my own. I provide a calm, loving, and safe environment and pay close attention to each pet’s individual needs and routines. I have over 25 years of experience caring for cats and kittens and understand the importance of patience, cleanliness, and keeping pets comfortable and stress-free. I’m happy to follow any special instructions, including medications, feeding schedules, and extra cuddle time.
About: I am a dependable and compassionate pet caregiver with hands-on experience caring for dogs and other household pets. I understand that every animal has its own personality and needs, so I take the time to build trust while providing attentive, personalized care. My experience includes feeding, walking, administering medications when needed, cleaning up after pets, providing companionship, and maintaining consistent routines to help them feel comfortable and secure. I am proud of my commitment to treating every pet like family. I pay close attention to behavior, energy levels, and overall well-being so I can quickly notice any changes that may need attention. I communicate regularly with pet owners, provide updates and photos, and always strive to give them peace of mind while they’re away. I am patient, reliable, and genuinely enjoy spending time with animals. Whether caring for energetic puppies, senior pets, or shy animals that need extra patience, I provide loving, responsible care that keeps pets happy, healthy, and safe. I work from home with generous breaks. While my schedule is 9-5, I wake early to go on walks in my neighborhood, and my work day includes 1.5 hours of breaks. After work is much like “before work”. A pet would work perfectly in this schedule I have a 3 story townhome and garage! I recently installed a fence! I will keep the pet entertained with fetch, and other stimulating games and puzzles

“Anum quickly became loved by our 4 dogs and 2 cats. She easily remembered all the details of their feeding and schedule. She fed the entire crew and kept them all happy during a long Easter Weekend. Our emotionally needy GSP and barky Aussie became good friends with Anum. Even our very shy dog came out of her shell !”

“Natalie is fantastic! Very communicative and I could tell from the questions she asked that she was going to provide great care to my cats on her drop-in visit. Everything went smoothly and I will definitely rebook!”

About: Hi! I’ve had a dog since I was a toddler and I’ve always been fascinated by dogs/pets, and caring for them. I love spending time with them, playing, walking and having fun! I’ve always considered them an extended part of my family, which makes me understand how importante they are in our lives and that they have needs just like everyone does! Part of those needs are caring, helping them keep themselves active, proper feeding and to stay healthy, no matter their age, breed or condition. Time apart from them can be tough, but by showing love and care, I help them to relax, have a good time, and to wait for you to be back with them! 🤗 I currently work part time, which gives me a lot of flexibility, and time to spend with my furry friends 🐶 I also have a car, that lets me move quicker and helps me attend my pet-guests 🥰 I have a large fence backyard and a sweet brown lab named Cocoa, who’s always happy to receive guests! In case our furry friend is not interested in having company, she likes giving them space. There’s plenty of room to keep them separate 🧘🏽
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?
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 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.
How to book dog sitting

1. Search
Browse profiles of sitters near you who offer dog sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
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 of Dog Sitting in Winchester is $22 per visit as of November 2026. Most bookings cost between $12 and $27 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 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.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
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:
- 91% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 98% 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 contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.











