Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 7 pet parents in Winchester have booked dog walking
Winchester, Find top rated dog walking
Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“I have used Cyrissa over 15 times and she has done a fabulous with my Luna. She responds quickly to my requests and is very communicative She gets Luna out for a good walk every time she comes- they go about a mile which I truly appreciate. I’m not paying her to take her out to just let her lay on the grass for the majority of the time (I’ve had other people do that). I want Luna to get out and exercise and Cyrissa does just that. I 100% trust her in my home and with my dog. I’m lucky to have found her.”
About: Of all animals I have the most experience with dogs. I love dogs all shapes and sizes We've always had a dog at home and I have lots of experience, caring for playing with and walking dogs, including bath time. I'm a recent graduate of heritage high school. I took agriculture at school and worked with the animals on our school farm I'm looking to do rover as often as possible. I don't have any other obligations at this time. So I can dedicate myself to your pets. I am very careful about fences and doors. I'm mindful of owner instructions regarding where their pets can be. And where they are not allowed. I am mindful of them while they are eaten. And while they are playing, to make sure that they remain safe. I checked the pavement before I take a dog out on walks to make sure it's not too hot and always make sure to wash their bowls so that I can help prevent bacteria
“Charles once on time , caring and considerate while my dog. This is the first time I used the walking service via Rover and my experience with was outstanding. I will be contacting him for future walks when needed.”
“Doobie had another great walk with Lamar. She is always sooo happy to see him, tail wags & butt wiggles. I can always count on Lamar to take good car of Doobie and her special needs!!!”
About: Hi! I have been caring for pets for over 20 years. Currently, I have a 2 year old 60-lb Boxer dog and I also had 3 Shih Tzus for 16 years so I am used to large and small dogs, energetic pups and senior dogs. I’ve taken classes with trainers that trained with Cesar Milan focused on dog psychology and calm confidence. I can care for senior dogs and administer eye/ear drops, medication, and gentle handling. I can also care for playful or large dogs and help get their energy out. I am available for short or long walks, short or long overnight stays, house sitting, companionship (and cuddles!), bathing, and drop ins. I have a flexible schedule and reliable transportation. I’m available for requests to care for your pets and am excited to meet your fur babies! I am very aware of my surroundings and doors/gates to ensure dogs to not escape or run off. I am diligent in making sure they don’t have something in their mouths that they shouldn’t. I have a high energy 2 year old boxer that I have crate trained and am used to taking all necessary precautions to make sure pets are safe and secure.
“Very kind and sweet. I appreciated the time given to get to know the pups during the meet & greet…as well as the feedback after their first walk. Would absolutely book again!”
“We cannot say enough good about Dawn! So communicative, so accommodating, and so awesome with our two doggos! 100% will be reaching out again next time we need a walker or sitter, and will be recommending her to any friends/family who need care for their pups! Thank you, Dawn!”
“Highly recommend! Took care of our 3 dogs while we were away and very tentative to instructions. Communicated perfectly if we needed adjustments and our dogs were so excited to walk with her when she arrived at our house. Will definitely use her again in the future! Thank you Keiona!”
About: Hello 👋🏻 My name is Kaylee and I’ve been a professional pet sitter for about 5 years now. Over the course of those 5 years I’ve cared for all of the following animals: dogs, cats, birds, fish, snakes, turtles, lizards, hamsters, rabbits and horses. I’m in college getting an animal science degree and I’ve worked with a wide age range of animals. From puppies all the way to senior dogs and kittens all the way to elderly cats. *please know that while my listed prices are accurate additional surcharges may apply. (All prices will be disclosed before booking) I have a lot of availability for pet care in my schedule, I do have college classes I must attend and the occasional appointment with these being non-negotiable blocks of time I must leave the clients home to attend (which will be discussed ahead of time). However aside from that I have a plethora of time available to dedicate solely to your pet(s). *jobs that are “constant care” and/or have strict rules regarding how long the pet(s) can be left alone WILL incur a surge charge. I haven’t had a pet escape or get lost on my watch yet, and I don’t plan to start now. My childhood dog escaped once as kid, and even thought he was quickly found, it made me realize the horror of potentially losing a pet. As a result, I take pet safety very seriously. I will not walk a dog without a leash. I always double and triple check that doors are closed/locked (when appropriate).
About: What sets me apart is the trust I've built with my clients. Many are repeat clients who feel comfortable leaving their pets in my care, even for vacations lasting over a month long. I'm reliable, highly responsive, and believe communication is key. I'll keep you updated with photos and messages while following your pet's routine to help them feel safe, comfortable, and loved. From tiny cats to large dogs, I treat every animal as if they were my own and every home with the utmost respect, so you can enjoy your time away with complete peace of mind. I have a flexible schedule, which allows me to provide pets with plenty of attention, exercise, and companionship throughout the day rather than just quick check-ins. Whether it's walks, playtime, feeding, or simply keeping them company, I enjoy making sure each pet feels comfortable and cared for. As a pet owner myself, I understand the importance of consistency and sticking to your pet's normal routine. I always strive to make them feel safe, happy, and loved while you're away. I believe pets are happiest when they can stick to their normal routine. During overnight stays, I provide full care including feeding, fresh water, walks, potty breaks, playtime, cuddles, and any medications or special instructions if needed.
About: • sellf insured • most of my pictures are of animals I have babysat & taken care of - I’ve grown up with animals, I always wanted to be a veterinarian, but I work rescue, I love all pets and whenever I see one I always wanna say hi and pet or give them a treat ( if allowed) I carry milk bones in my car for the homeless dogs around, I couldn’t imagine my life without animals, Ive taken care of dogs, from helping rescuing and taking care of others and my own, I’ve walked dogs from really big to small, I love animals and have always loved taking care of them, your pet will get the total care with positive reinforcement, some breeds I’ve watched over; cane corso, goldendoodle, chihuahua, Pomeranians, Great Dane, Aussie,German shepherd,& more! I will love and care for each needs of the animal as if they were mine I am currently waiting to get disability so I have a completely open schedule and I’d love to fill it with things to do and I love animals. I have 3 small dogs myself, 3 Pomeranians, 1 named ghost, Gracie & princess, I have recommendations from many people who I’ve taken care of their animals, I know how to crate train, distribute medicine, make food if needed, I also have rescued over ten animals that were dumped and made sure all those babies went to safe homes.
About: I have experience with all shapes, sizes and temperaments of animals. I currently own two large dogs. I have experience walking reactive dogs and fearful dogs. I have also cared for elderly pets and trained quite a few puppies! Knowing how particular I am with my own pets, I take your care instructions extremely seriously and will ensure you pet has nothing but the best while you are away. I work from home and am my own boss so my time is very flexible to give your pet all that they need! I can do check-ins or walks all times of the day. I am happy to follow your lead on whatever you like your dog to do every day! Backyard playing or walks around the neighborhood. Whatever your dog likes best, I can do!
About: I treat every dog like they’re my own. I’m patient, calm, and tuned in to each pet’s unique personality and needs. I have experience with both puppies and senior dogs, so whether it’s helping with basic training, keeping up with high energy pups, or providing gentle care and routine support for older dogs, I’m confident and comfortable doing it all. I pay close attention to behavior, body language, and comfort levels to make sure every dog feels safe and understood. I’m reliable, communicative, and I always go the extra mile to make sure pets stay happy, healthy, and stress-free while you’re away. Pet care fits easily into my daily routine. I currently work a part-time job, which gives me plenty of flexibility and time to give your pets the love, attention, and consistency they need. I plan my schedule around feeding, walks, playtime, and check-ins, so each pet gets dedicated care throughout the day. Whether it’s daily visits or longer stays, I make sure your pets feel safe, comfortable, and loved with a steady, reliable routine. When I’m caring for pets in a client’s home, I focus on keeping their routine as familiar and stress-free as possible. I follow your instructions closely, feeding schedules, potty breaks, walks, meds, crate time, and any house rules your pet already knows. I give plenty of attention, playtime, and check-ins so your pet feels safe and comfortable in their own space. At my own home, I have four friendly dogs, so visiting pets are welcomed into a social, loving environment. I make sure everyone gets along safely, and I supervise all interactions to keep things calm and positive. Your pet will get lots of companionship, enrichment, and affection while they’re here. No matter the location, I keep water bowls full, maintain a clean space, and send regular updates and photos so you always know how your pet is doing.
“My dogs have greatly improved in their stamina, and calmed their energy level! Erica has been a great help with my high energy dogs while I manage my older dog that just can't quite keep up. Super helpful!”
About: My sister and I had pets since I was a child. Frogs, fish, turtles, dogs/puppies, bunnies, and a parrot. I would say I am well rounded in pet care. I am able to board small dogs, I also can watch your furbaby in home if you like. If you need someone to drop in and take care of your pet while out I am also willing to do that. I know how to administer oral medications if that is of need. I currently only have two rabbits and a fish tank so your pet wouldnt interfere with any of mine. I board only one pet at a time so that I can give full attention to that furbaby. Making your pet comfortable and happy is what I strive for when you see your furbaby again. I am currently working from home so I have more than enough time to take care of your animal. I will be available to feed , and do any extra activities they your animal may need. I have a fenced in yard, and can crate if needed. Please bring your own crate I do not have extras at my home yet.
The median cost per walk for dog walking in Winchester is $25
Dog parents share their Rover experiences - Winchester
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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
- 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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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
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2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
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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 $23.31 per walk (as of August 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 August 2026, there are 3,483 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:
- 90% of walkers can help with special care needs
- 96% 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.
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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