Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 111 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 is amazing and I’m so grateful for her help in walking and checking in with my dog. She’s kind and communicative and sent lots of pictures which I appreciated. She was helping me with my dog but even made sure to spend some time with my cat when she stopped by! I’m looking forward to having her care for my pets again in the future.”
“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 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!
“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!”
“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!”
“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.”
“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. 🐾💕”
“Ashlee has been so kind and helpful to me and my pet babies! She drops in to check on my dog while I’m at work and I can’t thank her enough! She’s also been keeping an eye out for my cats when she drops in, just to make sure my dog Emma doesn’t get into anything. Ashlee has been such a blessing, whenever I have a concern with them getting into something, she always reassures me or communicates what’s happening. Also; she left some dog bags for me when I ran out, what a sweetheart! ☺️💖”
“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.”
“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: 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.
“Went above and beyond being available on a same day request 🙏 thank you for being patient and so caring to our pups! We appreciate you for feeding them and making sure their bowl was full with water! Looks like you all had a great time at the dog park as well 😁 thanks again!”
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: 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.
About: I work part-time in the food and beverage industry and have taken pride in taking care of my customers for 28 years. I love my job and enjoy making my customers happy! I can think quickly when emergencies or issues arise and will I will take great care in the treatment of your furry family member. I currently have 3 dogs of my own: 2 terriers and a Labradoodle. I've had dogs my entire life. They were my responsibility from feeding them to cleaning up after them to giving them baths and walking them everyday. This developed my love of dogs that would last my entire life. I can't think of a time in my life I didn't have at least one dog. I've also fostered 13 dogs at different times. I currently work part time and fill the rest of my days with caring for your fur pals. They will only be left alone when I am running short errands! I have a fully fenced in yard with a locked gate. I also have a large dog door if your dog likes that they can use it 24/7!
About: Hello my name is Nataly I’m a certified K9 Handler. I work full time with my own K9 her name is Eleanor. I have Knowledge in K9 care and CPR. I’m very passionate at what I do my job isn’t a clock in job in fact it isn’t a job at all it’s my passion, it’s a life style. I love working with dogs and all animals. My field provides me with the most updated knowledge in the K9 industry so that I can provide the best care possible for your dog. My most recent certification has been in K9 behavior. I’ve trained my own K9 and I am able to help with any training needed at an extra cost. Know if your dog stays with me I will provide the best care possible an for will be in the best hands.
About: Early mornings or evenings, I can take care of your furry family member anytime. I am a dog and cat sitter who has 5 years of experience taking care of animals and can house and plant sit occasionally. I am available to take care of your furry friend at any time of day. I enjoy and am skilled in walking, feeding and playing. I create a safe and welcoming environment in the home when introducing myself to your furry friend. I take great care and am patient with them.
About: I do not have kids so dogs are a great substitute for the everyday necessities I will need when raising my own children (except for playing fetch,..haha)...I also live with roommates that love to play & host pets that are visiting. So any visiting pet is always being attended to by caring people. I have a large home with a large backyard for free roaming. My dog Koda is very friendly to visiting dogs, he allows them to use his bed if they so choose. He is not bothered if they eat his food, he is just very happy when he has company & does not cause problems. We will take care of your family member to the day of pickup...Hope to see ya soon
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 July 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 July 2026, there are 2,347 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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