Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 112 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.
“Hannah gets a ten out of five paw review from Betsy and I. Hannah was absolutely wonderful! She took amazing care of Betsy, was prompt at communicating and just an overall wonderful person. I was super nervous hiring help that I didn't previously know but I'm glad we took a chance. We will definitely use Hannah again whenever we visit LV again.”
“Hilda spent the Christmas-New Years week with our pups and they loved her! Daily walks and occasional feedings. Hilda was exceptional - professional, kind, and thoughtful throughout. HIGHLY recommended for all of your Rover needs!”
About: I have taken care of dogs for at least five years. I have had dogs of my own pretty much since the day I was born! With that, means I’ve taken care of dogs from puppies, to old folks! I work part time, I’m off every day at 12 and free after that! For over night care they would only be alone for about 4/5 hours while at work! My front yard is partially fenced with a dog restraint so they can still venture in the grass, my back yard is fully walled in! And if your dogs love water we have a pool!
About: I grew up on a farm surrounded by all kinds of animals, so caring for pets has always felt natural to me. From a young age, I learned how to read different personalities, respect boundaries, and make animals feel safe and comfortable. That experience still guides how I care for pets today. I currently share my home with two dogs. One senior at 12, a kind and spunky Shepherd mix named Ozzy. A younger at 8, a gentle and playful Golden Retriever named Clint. I also have two rabbits named Sam and Frodo ( who Basically rule the house). So I’m familiar with different ages, energy levels, and routines. I understand how important it is to notice the small things. Keeping a calm environment, following feeding schedules, and making sure each pet gets the kind of attention that suits them best. Whether I’m walking a dog, checking in on a bunny, or helping a nervous pet settle in, I bring patience, warmth, and steady care. My goal is always to make your pet feel secure and genuinely looked after while you’re away. *BOARDING I do accept multiple dogs at a time! I ensure that all dogs I take in are friendly with other animals. If I feel a dog will not feel safe with my current pets I will inform the owner of this concern. It’s always maximum fun when boarding multiple dogs 😊
About: I have had dogs & cats my whole life! I can't imagine not taking care of a dog or cat! I'll never let any harm come to your pets! When your pets aren’t playing in my backyard, swimming in my pool, or doing their business they will have one of the guest rooms in my house to chill. Meet Ethel – Our Official Boarding Hostess 🐶 After I retired in June 2023, I began boarding and walking dogs through Rover and Wag. What I didn’t expect was to end up with a 50/50 business partner. Ethel joined my life officially on January 2, 2025, after boarding with me several times throughout 2024. She quickly proved herself to be calm, confident, and remarkably good at managing group dynamics. A few days after she moved in, I discovered something extraordinary: Ethel was born on my 58th birthday—the very morning I was out walking a dog named Cuda. Since then, Ethel has become the heart of my home-based boarding setup. She’s the official hostess, a natural leader during playtime, and the quiet enforcer of naptime. Boarding runs smoother with her here—less chaos, better routines, and happier dogs all around. Think of her as the technical advisor for playtime logistics… and my most valuable coworker. I will follow their owner’s exact specifications. As long as it is safe and healthy for the dog or cat, I'll follow the owner's directions verbatim! I have always fed my dogs and cats Science Diet pet food!
“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.”
“Shawn has been such a joy watching our dog! He’s definitely put our nerves to rest while away on vacation and seeing the videos of our dog being taken care of. Would definitely be using his services again!”
“Jorie walked our dogs all last week and did a great job! They were excited to see her each day :) We got thorough updates daily. We are already planning to book again. Thank you Jorie!”
“Rachel is a total gem! My dog absolutely adores her — tail wagging the moment she walks up to the door. She’s reliable, upbeat, and treats every walk like an adventure, not just a job. You can tell she genuinely loves what she does and connects with dogs on their level. She’s always on time, pays attention to every little detail, and handles my pup’s quirks with patience and good humor. When Rachel’s in charge, I don’t have to worry — I know my dog’s getting the exercise, care, and attention he needs. It’s such a relief finding someone who’s trustworthy, responsible, and fun all at once. Rachel isn’t just a dog walker — she’s part of the pack now! Highly recommend her to anyone lucky enough to book her.”
“Ashlee is so sweet with my dog Biggie. I know he looks forward to his walks with her. She made a point to meet before his first walk to talk about his likes and dislikes and to make sure he was comfortable around her. I will be using Ashlee for all of Biggie’s walks.”
About: Caring for animals has been a part of my life since I was 10 years old, it's honestly just who I am! Over the years I've fostered dogs (and proudly failed). Today, my partner and I share our home with 3 cats and 5 adorable Dalmatian-mix dogs. So I'm used to caring for multiple pets and large breeds. I've also cared for medically fragile animals and currently give my own cat daily medication for his asthma, so I am completely comfortable handling pets with special medical needs. I teach at UNLV on Mondays and Wednesdays, but beyond that I work from home running my freelance medical writing business which means I'm around most of the day, most of the week. Your fur babies won't be sitting alone counting the hours, they'll have a present, attentive and loving person right there with them! When caring for pets in your home, I follow every instruction to the letter. Whether it's feeding schedules, medications, exercise routines, or household rules. I am extremely detail-oriented and take my responsibilities seriously. I treat every pet as if they were one of my own beloved animals, ensuring they feel safe, loved, and comfortable in their own environment.
“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. 🐾💕”
“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: Hello, my name is Alexa (some friends also call me by middle name, Cecilia). I have been a dog lover and parent since I was young, and as an adult have gotten the opportunity to care for a variety of breeds and ages. I have experience with small breeds, senior dogs, and puppies/adolescent dogs in my own home as well as when friends and neighbors need some extra help. Medication regimens, playtime, training sessions, and of course some cuddle time are all in my comfort zone. Whatever accommodations you need for your pet, I am happy to provide and send photo/video updates while you're away! I currently have a part-time job in the evenings only a few days a week, and also take classes at UNLV. However, most of my schooling is online and my work schedule is very flexible as well. With that flexibility, I can be available in the Daytime and Evenings. For longer stays, extra notice will help me plan accordingly to accept the opportunity to care for your pets. Whether there's a backyard available or not, I'm happy to take your pet out and about to ensure they stretch their legs and get their sniff on. Depending on your pet's temperament and your comfort level, I can facilitate play dates or keep them company solo. Safety is important to me, and I treat every pet as if they were my own.
About: Lifelong dog & cat lover. After losing my beagle, Anna, after 14 amazing years together, I'd love nothing more than to spend time with your pups and give them all the love, attention, walks, and treats they'd ever want. Experienced with senior dogs, giving medications (pills and shots), and dogs with hearing or vision impairments. Whether you're working long days or vacationing away from home, do it without any extra stress and let me spoil and care for your fur babies. My schedule is open for the needs and care you need for your fur babies. I'm flexible and can work with you on what you need and when you need it. Safety and comfort are my top priorities when caring for pets in my home or yours. I treat every pet like my own and want to take the time to learn their routines, preferences, triggers, and quirks so they feel secure and loved while you're away. I have hands on experience caring for senior dogs, including those that are hearing or vision impaired, mobility differences and medication needs. In your home and with your pet, I respect your routine and instructions to help give your pets consistency to feel safe. You'll receive updates, photos and open communication to know how your fur babies are doing.
“Sierra loves animals as much as I do, is prompt with our walking schedule, and is willing to go the extra mile. I couldn't recommend her enough if you're in need of her services. She's welcome to take care of my Eva for as long as she's willing.”
About: Pet parents and lovers! We use Rover for our pets when needed, so we understand the importance of finding someone who is trustworthy, reliable, and responsible, but also someone who can make your pet feel a little less alone when you are away. Let us be the break your pet needs throughout the day! We do walks, dog parks, stop-in visits, brief home visits, or longer stays (up to two weeks - and at our place only please). We also do baths, play time (obviously!), and errands. We can also follow any training techniques in place. I’m self employed, running a nonprofit that serves veterans and first responders. We advocate and bring awareness to suicide prevention and mental health initiatives. Since I’m self employed, and given the nature of the daily operations pertaining to my job, I have flexibility. Our “dog proof” home comes with a large, fenced in backyard. We have a doggie pool, all basic dog supplies, dog training supplies, all basic cat supplies, leashes, etc. If we are traveling to your home, we suggest that you send us clear, step-by-step instructions and any expectations you may have, and trust that we will exceed your expectations. We genuinely just love animals and want to help out other pet owners while making a little cash.
About: Currently have 4 dogs at home and 5 cats! We own a small terrier all the way up to a German shepherd. Comfortable with any breeds and with cats and can guarantee they’ll be cared for as if they’re my own. I work full time but will be off for the next weeks so I can dedicate more time. Once I go back to work I’ll adjust my schedule accordingly. We let ours dogs run free when we’re home and are kenneled at night or when we’re away. Also have a fenced yard where they can run.
About: I’ve taken care of my dogs of all kinds since I was thirteen years old. My neighbors and family have relied on me to take care of their pets by walking, feeding, and bathing them. I have plenty of schedule open! I always love takes cares with dogs or cats everyday! I can do open morning or evening for you. I always safe dogs or cats in fence all time. I know do put crates all time. I always check on them everyday or anytime.
The median cost per walk for dog walking in Winchester is $20
Dog parents share their Rover experiences - Winchester
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.
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 $16.65 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 2,337 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
- 96% can help with giving oral medications or injections
- 99% 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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