Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

Over 110 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.
âHannah 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.â

About: Cleaning, feeding, and petting, are my specialities when it comes to dogs. I haven't really trained dogs, besides the basics, but I love spending time with them. I'm currently unemployed (looking for a source of steady income), so I'm available to watch your furry members of the family any time starting in December. Most anything that you need for your pet, I can do. I love learning what my clients expect from me and will do the best of my ability.
âDelightful, diligent, and funny. I get really thorough summaries of Snookyâs walks and it gives my anxious brain peace oâ mind. Also, the photos are always of Snookyâs good side!â

âJorie 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!â

âZuko 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.â


About: Im open to all dogs all sizes and willing to do what it takes for your pet to be safe and comfortable! I grew up around dogs and have one of my own. Ive been dogsitting for a couple years and know what it takes to make a pup feel safe and secure. I love taking cute pictures and videos, I always make sure to update regularly. I can care for puppies to seinors! I am currently on summer break from college and ready and available to be a full care taker. I am available all days of the week! I have a big fenced in backyard with a doggy door for full time access. I have a 6 year old super friendly fulled trained labradoodle to keep your pup company. At your house I am very respectful of the space im in and can follow instructions very clearly, safety is my first priority. I will always send updates and photos frequently. I am very good at adapting to situations when needed and thinking on my feet.
âHilda 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!â


âNatalie was amazing with Odin I really needed someone who can handle his energy and keep him separated from other dogs she was very kind and overall did the best she could to accommodate me and my dogs needs I will definitely be using her again! Thank you again!â

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.

About: Iâve grown up around dogs my entire life and have over 12 years of experience caring for them. I understand that every dog has their own personality, routine, and needs, and I always make sure they feel safe, comfortable, and loved while in my care. I enjoy giving dogs plenty of attention, playtime, walks, and affection, and Iâll treat your dog like theyâre part of my own family. Im currently in nursing school and also work, so my schedule can vary from week to week. My calendar may sometimes look more limited than my actual availability, and I can often be flexible depending on the day and your pets needs! Please feel free to message me even if a date appears unavailable- I'm always happy to see if we can work something out. I only accept bookings I can fully commit to so your pup gets the time, attention and care they deserve! I always make each dogâs safety and comfort my top priority. I follow the ownerâs instructions closely, including feeding schedules, walks, medications, and routines. I make sure pets receive plenty of attention and supervision, and Iâm happy to provide regular updates and photos so you can feel comfortable while your pup is in my care.
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 arenât 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 â Our Official Boarding Hostess đś After I retired in June 2023, I began boarding and walking dogs through Rover and Wag. What I didnât 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 birthdayâthe very morning I was out walking a dog named Cuda. Since then, Ethel has become the heart of my home-based boarding setup. Sheâs the official hostess, a natural leader during playtime, and the quiet enforcer of naptime. Boarding runs smoother with her hereâless 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 ownerâs 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!
âShe did great with my newly rescued dog that hasn't been trained yet! He's SO BIG! Yet she managed to walk him and help Tucker him out!! Thank you!!â

âI canât recommend Jamie enough! She was incredibly reliable and was willing to step in last minute to walk Chewy when I had to leave for a trip. Chewy absolutely adores her. He waits by the door for her knock and gets so excited every time she comes by. It gave me so much peace of mind knowing he was in such good hands. She was truly the best dog walker we could ask for!â

âAwesome 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.â
âSierra 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.â

âFirst time using rover and Mariana is a blessing. She is amazing, attentive, communicates about the doggos and is punctual. Honestly she's made this experience smooth. I was so nervous but she's eased my mind. I highly recommend her.â

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. Iâm self employed, running a nonprofit that serves veterans and first responders. We advocate and bring awareness to suicide prevention and mental health initiatives. Since Iâm self employed, and given the nature of the daily operations pertaining to my job, I have flexibility. Our âdog proofâ 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.
âElena is very responsive and professional. She communicated with us regularly during her visits with Fergie, checking in before leaving for our house and before leaving our house, and sent pictures during her walks. Fergie responded well to Elena, and seemed to like her a lot. We highly recommend Elena!!!â
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! đđž

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 appâlots 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. đžđ

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 couldnât have asked for a better dog walker. She is incredibly trustworthy, kind, and genuinely attentive to Killerâs 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. Sheâs always helpful, thoughtful, and communicative, which gives me complete peace of mind knowing heâs in such good hands. Iâm 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 teamâhere to help if you ever need someone to talk to.

Why Choose Rover?
Cashless payments
Book and pay through Roverâs secured platformâno cash or checks required.
Reservation protection
It doesnât happen often, but if your sitter has to cancel, weâll work with you to find a new sitter.
World-class support
Weâre 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 September 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 September 2026, there are 2,366 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 dogâs 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 dogâs walk begins.
The Rover Guarantee is Roverâs 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 Justiceâs 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
- 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.





