Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 135 pet parents in Winchester have booked dog walking
Winchester, Find top rated dog walking
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“We’ve hired Kim a few times to feed and walk our dog. She is very reliable and friendly and takes great care of our dog. The Winchester community is lucky to have someone like Kim to look after our pets :)”
“⭐️⭐️⭐️⭐️⭐️ A True Gem – Like Family to Us and Maximus! We feel incredibly lucky to have found Hannah—she’s not just a dog walker, she’s part of our family. Our dog Maximus is truly our baby (especially now that our kids are grown and out of the house), and knowing that Hannah cares for him with the same love and attention we do means the world to us. Hannah has been with us for over three months now, and in that time she’s become someone we fully trust with our most spoiled and beloved family member. She’s reliable, flexible with our crazy schedule, and always greets Maximus with affection and warmth. You can tell she genuinely loves what she does. Maximus absolutely adores her! She goes above and beyond to make sure he feels cared for when we’re not home, which gives us such peace of mind. We treasure Hannah and everything she does for our family. If you’re looking for someone who will love your dog like their own, look no further. She’s truly one of a kind.”
“After 16 years, we finally decided to try a dog walker with our dog. We couldn't have picked a better person to trust her with! After meeting Meghan we felt very confident with her taking care of Lily. We will definitely use her again.”
“Alyssa was very professional and everything went perfectly smooth! She braved the wind and rain and made sure to update us that he went #1 and #2 which is always important for us pet parents to keep track of lol. She made sure she had time to snuggle with him before she left, and filled his water bowl. I could tell Dingo was content when I came home! I will definitely use Alyssa again in the future”
“Sherry took our menagerie of dogs and cats in stride when she arrived and she handled my dog Duncan with ease during the walk. She obviously loves animals and my dog, who is sometimes shy with strangers, immediately liked her and will be happy to see her the next time she comes. I highly recommend her if you need a good caretaker for your pets.”
About: Hello, my name is Sierra! As a dedicated pet owner myself, I understand the deep bond between animals and their families. With over 7 years of experience caring for dogs and cats of all breeds, I've honed my skills in providing compassionate and reliable pet-sitting services. I'm excited to extend my love for animals to your furry friends. I am seeking a rewarding opportunity to utilize my free time. I'm available most days and times and would love to offer my services as a reliable and compassionate pet sitter. Your pet will feel right at home in my caring environment. I offer a safe and fun outdoor space, as well as cozy indoor comforts. I'm flexible and adaptable, ensuring that your pet's needs are always met.
“Lisette is great with my dogs! We have an older dog that she comes and walks and he loves it. We also just got a puppy and she has been coming over in the middle of the day to take him and our older dog on small walks and it’s been great!”
About: I’ve loved animals my whole life, and I’ve had the pleasure of living with, and pet sitting for multiple cats and dogs. I’ve done both kitty and dog meds, so if you have a high maintenance fur child like me, I’ve got you covered!! If you trust me with your fur baby, I promise I will love them as much as I love my own!! I work from home, so I have a lot of flexibility. Mornings are more difficult for me, but I can definitely work with you to find what’s best for the pets! My own pets are high maintenance, so I am definitely able to work with your pets needs. I crate my own dog, and give both my dog and cat meds and supplements. I don’t have any human children so my pets are my children. I will give your pet the love, attention, and care I give my own!!
About: I’ve taken care of dogs and cats of all sorts. I grew up with small, medium, and large dogs as well as indoor and outdoor cats. I’ve also grown up caring for animals from a variety of backgrounds- fosters, rescues, you name it. I genuinely love spending time with animals and since I can’t have one of my own this seems like a great way to connect with pets and offer my services. I’m happy to come meet any animals in advance to make you more comfortable. I currently work remotely 90% of the time so this gives me a lot of flexibility to walk and take care of animals during work day hours if needed. I’m very good with following whatever directions will make you and your pets feel the most comfortable in your homes and out on walks.
About: I have had dogs my whole life and I have had a cat for the last 7 years. I am very good with animals and I love them very much. I have also babysat my own dogs when my parents go away as well as my aunts cats, and my neighbors dogs and cats. Since I've had many animals in my life, I know how to take care of them and I know how to tell what they need. I am in college but have many hours throughout the days that I am available and I am also free most nights (though I would need notice incase I make plans with friends) I am available all day on Mondays, available from 11-2 and after 5:30 on Tuesdays and Thursdays and available all day besides 2-4 on Wednesdays and Fridays. I am also available all day on weekends I would just need to know in advance due to plans. I will offer your pet lots of love and will do whatever is best for your pet! I can easily crate your dog and I love long walks and would be happy to go on one with your pet.
About: My family has had 2 dogs since I was 10 and two cats since I was 14 which I took part in caring for. Four years ago I also got a cat of my own! I have been fortunate enough to also care for pets from different friends and families while they’ve been away! So, I have a lot of experience feeding, playing, cleaning up after and caring for cats and dogs of all different breeds! I am currently in PA school so I have class from 9-5 Monday through Friday but I am free to help before and after school and on the weekends! I am great at following any directions from you to ensure that your pet is safe with me! You let me know what standards and precautions you follow and prefer and I will always abide by them!
About: I’m new to the area and looking to help out with the furry friends in my neighborhood! I’ve grown up around dogs and cats since I was young, and love getting to spend time with them, whether it be taking them on walks/runs, playing with them, or just giving them lots of love and attention. I am reliable, with my own transportation and a flexible schedule! I am a new graduate student at Shenandoah University - as a musician I have a few rehearsals in the afternoons and evenings, but my schedule is pretty open otherwise and I’ll have plenty of time to stop by/stay over and keep your pets company! I am a rule follower! I will follow your guidelines to a T, and make sure your pet is cared for exactly as you wish. I know that pets are our whole world, and leaving them with a stranger can be nerve wracking - I am reliable and responsible, and you can easily trust me to take care of your loved ones!
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 am a husky lover and owner who has spent most of my life taking care of dogs! I am 30 years old and have grown up taking care of beagles as well as pet sitting for family members and neighbors. Now, I currently have two huskies, ages 3 and 1. I enjoy long walks with my pups and lots of play time! On the weekends, I enjoy taking my dogs on long hikes, taking them to the dog park for some play time and even runs on the beach. My huskies are friendly with dogs their size and love making new friends. They also have spent time around cats and although they avoid playing, they do love other furry friends. My energetic attitude and love for animals makes me the best match for the job.
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!
The median cost per walk for dog walking in Winchester is $20
Dog parents share their Rover experiences - Winchester
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.
Meet local walkers who will treat your dogs like family
1. Search
Browse profiles of walkers near you who offer dog walking
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 walking - Winchester
Select a filter and find qualifying sitters offering dog walking.Sitters in Winchester average 3 repeat dog walking clients
FAQs for Dog Walking - Winchester
Frequently asked questions about Rover
The average cost for Dog Walking in Winchester on Rover is $21.4 per walk (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Walking 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 Walking. For more information on service fees, click here .
As of September 2026, there are 824 sitters on Rover offering Dog Walking across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.
Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Winchester. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winchester.
Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.
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.
Every walker 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 .
Yes, you can find walkers who have experience with handling special pet needs in Winchester. On Rover:
- 93% of walkers can help with special care needs
- 100% 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.
A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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 walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers 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.
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 walker.
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