Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 133 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.
“Crystal has been wonderful! She came over to meet my dogs before the first walk. The dogs love her and I have a peace of mind that my pups are taken care of during my long days at work!”
“Jamie was absolutely wonderful with our sweet Bruno! She was reliable, communicative, and kept us updated throughout our trip with lots of pictures and messages, which gave us so much peace of mind. Most importantly, Bruno adored her, and it was clear she genuinely cared for him and took great care of him while we were away. We really appreciated her kindness, attention, and consistency. We would not hesitate to book with Jamie again and highly recommend her to anyone looking for a trustworthy and caring pet sitter. 🐾💕”
“Sierra is very knowledgeable and friendly, and our pups absolutely love her. Communication is wonderful, and she gives the best updates that help provide peace of mind.”
“I am really happy to have found Elena to take care of my dog while I traveled. She is a great communicator, shows up as scheduled, was very flexible and easy to work with, and all of my pets were very comfortable around her. I was so happy to have peace of mind while away and will definitely use Elena again in the future. Thanks Elena!”
“Awesome walker, great communication, kept me updated on the pups and got some pics along the way. Super nice about the whole thing and was great about meeting the pups on her own since I was already at work. 10/10 recommend.”
About: I’ve worked with dogs since I was 13. Weather it’s been working with new puppies or elderly pets I’ve seen it. Doing day to day walking and pet sitting. I take care of the pets so they can stay on a schedule. I’m currently a student at UNLV, but my schedule allows for plenty of time to be around, walk, and play with your pets through the day. I care for pets in their own home by following the same routine as the owner. Feeding on schedule, refreshing water, handling walks, and bathroom breaks. Keeping their environment clean and safe with plenty of attention.
“Zuko loved his walks with Maliki! This was the perfect match and Maliki was very calm with our big boy (German shepherd/husky), flexible with our schedule and always professional. We felt extremely comfortable having Maliki work and walk Zuko. We would love to work with him again either for walks or more doggie training; would highly recommend Maliki.”
About: When I was 12 I started walking dogs and at 16 I started house sitting for very young and very old dogs alike. I grew up in a house with at least 3 dogs at all times. I worked at a humane society then went on to volunteer for many years. I have worked with puppies, old dogs that need extra care, and pups with troubled past that may not be as trusting. I understand your pups are not just animals they are family members. I am here to make sure you and your fur babies are happy and stress-free! A tired dog is a good dog. Walking and playing are perfect ways to tire your pup out, so while you are away I can step in and give your pup the play time s/he needs. Lastly, some dogs need socializing to be able to come out of their shell more, I am an experienced owner of a troubled pup and I can completely handle this situation as well.
About: I grew up in a small town in Poland, we always had a house full of pets that everyone cares about. Currently back home we have 4 dogs, that I really miss. With my husband we currently don't want to commit to having a pet ourselves because we plan to travel but we really miss being surrounded by pets, we would gladly share our love to animals. I work from home so I have full availability, my hours are flexible so I can fully focus on pets needs while caregiving. Both weekends and weekdays At my place we have lots of space and safe, fenced huge backyard. While sitting at clients home, I can adjust to any space and take care of the pet and the space.
About: I was raised in Southern California, but more specifically Temecula. My grandma lived in San Diego area. Whenever she visited us or we visited her we always took her dogs out for walks twice a day. This love for taking dogs for walks carried through when our family owned a ratterrier mix with my family for about 13 years. I continued to walk dogs when I attended college in Mid Costal Maine. I helped walk dogs for the locals whenever I was not attending classes. I have always been an active lady. I played soccer for most of my life: elementary to college. I understand the commitment to keeping a schedule and detail to perform the activity to the desired outcome. I'm currently unemployed right now. I came back to Nevada to help with some family stuff. But spending time outdoors and letting your dog outside to stretch their legs let us enjoy the healing ability of walking away our troubles. I have become accustomed to the Southern Nevada heat for an hour or longer walks each day. I have the endurance if your pet needs to be taken at a certain time and distance.
About: Hello! I have two cats who are my best friends but I love all animals. I've taken care of small and large dogs and indoor and outdoor cats (even a cat who likes to go on walks with the dog!) and cats and dogs who take medications or have special needs. I am currently working part-time in the afternoons Monday-Thursday so that leaves the mornings, evenings, as well as Friday-Sunday open for me to spend time with your pets according to their needs and your innstructions! I will treat your home and pets with respect and care for them as if they were my own. I'll also send you pictures are updates while you are away so that you can have some reassurance that your beloved animals are safe and content.
About: I’ve cared for pets through Rover in the past during my undergrad years and continued to pet sit occasionally while living on the East Coast. Spending time with animals has always been something I truly enjoy, and I’ve missed having pets around. Now that I’m back home with family and working from home full-time, I have the flexibility and availability to provide attentive, loving care. I recently decided to rejoin Rover because I genuinely miss caring for pets and want to offer pet parents peace of mind knowing their fur babies are with someone calm, caring, and reliable while they’re away. Pet care fits really naturally into my daily routine since I work from home. I’m able to plan my day around walks, feedings, playtime, and check-ins, rather than squeezing them in before or after work. Being home most of the day allows me to give pets consistent attention, follow their routines closely, and respond to their needs as they come up. I enjoy building care into my day and making sure pets feels comfortable, safe, and cared for while their parents are away. When caring for pets in their home by sticking closely to their routine and making sure they feel safe, comfortable, and cared for. I follow and respect all care instructions provided and any household guidelines. I do my best to make sure pets get enough attention while also respecting their space and personality. I also prioritize keeping the home clean and secure during visits. I’m happy to provide regular updates and photos so pet parents feel confident and at ease while they’re away.
About: I’ve taken care of my own dog, Ky, since she was 11 weeks old. I’ve dog and house sat for numerous friends, either dogs ranging from small chihuahua mixes to large pit bull mixes. I work remotely so I am always on with my dog. We go out every couple hours on long walks, adjusting for the heat of course. Since my schedule is so flexible, I can give any dog the attention it needs. I am completely equipped to walk your dog, take them to the park or care for them in your home. I follow the parental schedule and feedings and am a frequent communicator.
About: Hi there! I’m an experienced and loving pet caregiver who offers all-in-one care for both dogs and cats including sitting, walks, and check-ins. Whether your pet needs daily exercise, overnight snuggles, or just a quick visit for food and playtime, I make sure they’re safe, happy, and cared for as if they were my own. I know every pet has their own personality and routine, so I take the time to get to know what makes yours feel most comfortable. From high-energy pups who love long walks to cats who just want a calm companion, I tailor my care to meet their needs. You can count on me to be reliable, attentive, and to give plenty of love, belly rubs, and treats (with your permission, of course 🐾 I have plenty of time to book for all services except boarding. Please message me or send me a request. Open availability until end of summer. When I’m caring for pets in your home, I always provide a safe, clean, and loving environment. I follow your pet’s routine closely, give them plenty of attention, and make sure they feel comfortable and cared for. You can trust that your furry friend will be safe, happy, and well-loved in my care.
About: I love love love animals and pets of all shapes and sizes. Ever since I was born, I have had one kind of pet or another, so I have lots of experience caring for them and loving them. I believe pets are family and they deserve to be treated as such. I am reliable and have experience with human society volunteer work and have 2 dogs and 2 cats of my own! I look forward to working with you and your pet (: I currently just relocated from SD for job growth and opportunity. My company is extremely flexible, and I am able to make my own schedule, so I can always make time To care for your pet! I can easily follow any directions asked of me to make sure your pet keeps their routine and stays safe while you're away. I will respect you, your pet and all your things.
About: I recently lost my dog after 17 amazing years. I’m not ready for one of my own yet but I hope I can give your dog the best time of their life. Right now for summer I’m available full time, all days of the week. I’m available to do boarding, drop-ins, and daycare. I am flexible to all options. I have a dog to keep yours company. My condo has a grass area and I will gladly take your dog across the street to Charlie Fries park to play.
The median cost per walk for dog walking in Winchester is $20
Dog parents share their Rover experiences - Winchester
Lilli was incredibly caring and patient with my dog. She took the time to learn about him and made sure he was well cared for throughout his stay. She communicated with me regularly and even sent me the cutest pictures of my baby! I could tell he was happy and comfortable with her. I would definitely recommend Lilli and would happily have her care for him again! 💕🐾
I feel very lucky to have found Hannah. She was amazing with my dog and I genuinely looked forward to reading her updates every day. She did such a great job using the app—lots of photos, tracking their walks, meals, poops and pees, and writing detailed updates about their time together. It gave me so much peace of mind knowing my pup was in such good hands. I would happily book with Hannah again.
Jamie was absolutely wonderful with our sweet Bruno! She was reliable, communicative, and kept us updated throughout our trip with lots of pictures and messages, which gave us so much peace of mind. Most importantly, Bruno adored her, and it was clear she genuinely cared for him and took great care of him while we were away. We really appreciated her kindness, attention, and consistency. We would not hesitate to book with Jamie again and highly recommend her to anyone looking for a trustworthy and caring pet sitter. 🐾💕
Zuko loved his walks with Maliki! This was the perfect match and Maliki was very calm with our big boy (German shepherd/husky), flexible with our schedule and always professional. We felt extremely comfortable having Maliki work and walk Zuko. We would love to work with him again either for walks or more doggie training; would highly recommend Maliki.
I couldn’t have asked for a better dog walker. She is incredibly trustworthy, kind, and genuinely attentive to Killer’s needs. From day one, it was clear how much she truly cares not just about doing the job, but about building trust and comfort with him. Killer absolutely adores her, and seeing how excited he gets says everything. She’s always helpful, thoughtful, and communicative, which gives me complete peace of mind knowing he’s in such good hands. I’m beyond grateful to have found someone who treats him like her own. So happy I found her and I continue to use her weekly .
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 walking
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 of Dog Walking in Winchester is $17 per walk as of November 2026. Most bookings cost between $13 and $27 per walk. On Rover, walkers 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 2,376 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 Winchester. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.
The route map lets you review where your dog was walked in Winchester after the booking. It is not live GPS tracking.
Have specific details you would like included? Message your dog walker in the app before the 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:
- 90% of walkers can help with special care needs
- 92% 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 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 walker 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 walker 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 walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
walkers 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 walker.
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