Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 70 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 are so blessed to have found Maria to walk our dog, Aria. She's been walking Aria 3-4 times a week for a year now, and she loves Aria like she's her own. I could not speak more highly of her. We love, Maria!”
About: I have 3 dogs of my own and have cared for many! For long periods or short periods, I know how hard it is to trust someone to watch your pups. My house is completely dog proof at this point. They will definitely be in good hands! I started rover because as a pet parent, the thought of finding someone to trust with my dog makes me so nervous. I really want to ease others minds and know their dog is in the hands of someone who LOVES to do this. I really enjoy making these dogs happy and taken care of. I truly treat them like my own, which is like my children! This is now my full time job so I will be home fully with your pet unless I have other drop-in visits to complete. My dogs are very friendly and like playing with others. Each of my dogs are AKC certified CGC (canine good citizens). My yard is fenced in and completely secure. My house is doggy proof, no one is eating anything they shouldn’t on my watch! Everything that a dog could get into is put up. I have a pool opened in the summer with stairs that the dogs can go into, also separately fenced for the pups that can’t swim. Keeping a clean and sanitized house is important to me for my dogs and your dogs health. My couch covers are washed weekly and my floors and my dog’s crates are cleaned with kennel sol which kills most dog related illnesses. My dogs are vaccinated. You are more than welcome inside my house to see the set up!
About: I am a certified professional dog trainer and was a veterinary assistant for over 8 years. I have over a decade of experience caring for animals large and small. I have ample experience caring for pets with mobility issues, incontinence, kidney disease, diabetes, anxiety, or other illnesses. I can provide gold standard care regardless of your pet's needs- including oral, topical, or injectable medications, subcutaneous fluid therapy, or just being a patient and calm friend to a fearful friend. I love and care for dogs and cats equally! I currently work a full-time 9-to-5 but have a somewhat flexible schedule within those hours. Early mornings, lunch breaks, evenings, nighttime checks, and weekends are all available options. If taking your pet out of the house, I like to have a fit check of your leash/harness or collar setup first. If your pet is known to be a "houdini" who can escape their gear, I may recommend alternatives and can help you with fitting your pet appropriately and/or bring a second form of containment with me (such as a slip leash used at vet offices) to ensure your pet's safety.
About: Ive taken care of dogs and cats all my life I personally have 2 dogs and one cat. Ive lived around animals my whole life and love them all dearly. I am currently a college student and I am in a musical theatre production but I will have plenty of time for your pets in between classes and before and after rehearsals! I will give your pets all the attention I do not offer services in my home because my cat is very jumpy but I will gladly come over and keep your baby company, walk them and feed them.
About: I have been around pets my whole life, but dogs are my favorite! I love them all, from puppies to the senior friends. I regularly care for my family dogs and I have experience caring for friends dogs and I have several regular clients. I have experience with puppy care and training, bathing, feeding, and administering medication. I also have experience with senior dog care nearing the end of life and all others in between. I have no trouble creating the special bond needed with most dog personalities. Dogs are truly our best friends! I play and exercise my own dogs daily. I understand the importance of keeping dogs engaged, healthy, and active. I do have a part-time job, but schedules are flexible given enough notice. I am so excited to care for your pup! I like to make sure the doggie is a happy, tired doggie when I do have to leave them. They love me and know fun is in store when I’m around. I play fetch and frisbee in the backyard and go on long walks around the neighborhood. If we can’t be outside I’ll play games with them indoors to challenge their minds and keep them occupied. Then of course there’s snuggle time together until they’re ready to nap or go to sleep in their crates or bed.
“Sloane is an absolute gem. She is conscientious, dedicated, and thorough. She takes care of our basket-case of a rescue dog several times per week and has been our savior from the ridiculousness of his unending energy and anxiety while we’re away. Her report cards are filled with humor and have us laughing out loud every time. Cannot recommend her enough!”
About: Greetings, valued customers, my name is Jordan. I appreciate you viewing my profile to get to know me a little better. I kindly ask that you read my profile in ENTIRETY so you have a better understanding to determine if we are a great fit and for detailed scheduling information down below. I look forward to hearing from you and I'm delighted to be here for all your animal care needs. I have cared for fish, dogs, cats, parrots and other birds, bearded dragons, snakes, chickens, goats, bunnies, doves, mini horses, pigs, other farm animals, and other reptiles, amphibians and exotic animals. I have been offering animal care services for eight years, and I completely love and enjoy doing it. The love that animals have for humans is an incredible thing to experience. Caring for animals makes my life so much more meaningful, and I love doing it for people who need my services. Also, knowing that people need my animal care services, fulfills my passion for helping others in life. I love and enjoy being of service to others, and it makes me so happy to be able to do so. I'm currently working as an RBT (Registered Behavioral Technician) (I work with people with autism and help them better adapt to everyday life), and I work with Rover as a petsitter as well. If you contact me for a lenghty petsit, I am able to ask off work with no complications (with more than a 2 week notice), however if you are in need of a speedy petsit, I can work with your schedule (but I may have to work a few hours during the day on week days, with no complications). My Rover calender will reflect my availability will continually be updated. Please check the calender before reaching out. Thank you for your understanding. I prefer going to a client's house to take care of their animals in a familiar environment, along with a detailed list of instructions of do's and dont's for their pet. Instructions on animal care are to ensure the animal's safety when they are with me, without me needing to unnecessarily contact and bother the owner while they are away. Also, a general list of outdoor activities I can do with the pet is welcome. For example, if I can take the pet hiking, to the park, for walks, etc. Also, does your pet get along with other animals, children, or people well, and does your pet get car sick? These variables are essential information for me to know to ensure the best care while you are away. My passion is pets, and I want to ensure your pets are comfortable and safe with me, so I highly encourage more than enough information on caring for your babies. Please note if your location is 40 miles, plus, in distance from my Rover given location, I charge for milage, for the traveling/distance in the initial reservation contact message for meet and greets. I will send you a new quote to your initial request for these changes in price due to milage charges. Thank you for understanding this policy.
About: I have been training dogs since I was 12 and sitting for 6 years now. I find the most joy in being with animals of all kinds. My experience doesn’t stop at dogs. I have cared for cats, horses, chickens, ducks, bunnies, fish, and so many more. I just moved to the area and I am trying to build up my clientele again. My schedule is pretty wide open right now as I wait for my next training in May 2027. My home is not conducive to boarding other peoples animals but I will happily care for them in the comfort of their own home where they are comfortable and have everything they need, while I pour my time and energy into them!
About: I had cat and dogs my whole life and owners pets mean the word to them care and gentleness mean the word to them I love pets I am available every day if you need your pets taking care of at anytime of the day you can get hold of me and I make sure I am there If you have any requests for your lovable pets let me know I will do my very best to make them comfortable as possible at all times
The median cost per walk for dog walking in Winchester is $18
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- 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
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It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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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 $20 per walk as of November 2026. Most bookings cost between $13 and $28 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 730 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:
- 91% of walkers can help with special care needs
- 95% 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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