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

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Top rated Winchester dog walkers
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“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.”

“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!”

“I can’t 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!”

“Delightful, diligent, and funny. I get really thorough summaries of Snooky’s walks and it gives my anxious brain peace o’ mind. Also, the photos are always of Snooky’s good side!”

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 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
“Deanna does a great job walking our hyper puppies. She works on training them to get them to walk next to her and focus on her rather than the many distractions outside. We continue to book Deanna because she does a wonderful job.”

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!
“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.”

“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.”
“Fantastic walker. Great communication. Walks my 11 week old that just got 2nd set vaccines and still needs third set in 4 weeks. She listened to my instructions to keep pup away from regularly walked areas of my condos. Plays with her. Really great with dogs. I felt safe entrusting the life of my puppy to her. I have her on repeat!”

“First 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.”

About: When I was 12 I started walking dogs and at 16 I started house sitting for very young and very old dogs alike. I grew up in a house with at least 3 dogs at all times. I worked at a humane society then went on to volunteer for many years. I have worked with puppies, old dogs that need extra care, and pups with troubled past that may not be as trusting. I understand your pups are not just animals they are family members. I am here to make sure you and your fur babies are happy and stress-free! A tired dog is a good dog. Walking and playing are perfect ways to tire your pup out, so while you are away I can step in and give your pup the play time s/he needs. Lastly, some dogs need socializing to be able to come out of their shell more, I am an experienced owner of a troubled pup and I can completely handle this situation as well.

About: I provide attentive in-home dog sitting with feeding, fresh water, daily walks, and lots of affection. I follow your dog’s routine closely to keep them comfortable and stress-free. Your dog will enjoy structured walks, playtime, and consistent care based on their usual schedule. I send daily photo updates and make sure they get plenty of exercise, attention, and love. I work part-time, which allows me to be available most afternoons and evenings for dependable dog and cat care, including walks, feeding, and check-ins. I provide personalized care based on each pet’s routine and needs. In a client’s home, I follow their feeding schedule, ensure fresh water is always available, provide walks for dogs, clean litter boxes for cats, and spend quality time playing or giving attention. I keep the home clean and respect all instructions. If caring for pets in my home, I provide a safe, comfortable environment with plenty of supervision, playtime, and a consistent routine. I make sure pets feel relaxed and at home while maintaining their normal habits as closely as possible. I also provide regular updates with photos so owners feel confident and connected while they’re away.

About: Loving, Attentive, and Reliable Pet Care — Tailored to Your Pet’s Needs! Hi! I offer professional, compassionate care for dogs and cats through boarding, walking, and drop-in visits. Whether you have a playful puppy, a senior companion, a pet with special needs, or a high-energy pup that’s hard to tire out — I’m here to provide personalized care in a calm, safe, and loving environment. I've had lots of experience with animals — from volunteering at a shelter for 3 years (working once a week), to having pets of my own since I was 5 years old, both cats and dogs. On top of that, my mother is a veterinarian and has been since I was 7, so I’ve grown up in an environment where caring for animals was second nature. I'm well-versed in animal behavior, handling, and overall care thanks to a lifetime surrounded by animals and professionals. As someone who works from home with a flexible schedule, your pet will never be left alone — they’ll receive constant attention, companionship, and care throughout their stay. I pride myself on being punctual, communicative, and dependable, and I go the extra mile to make sure your pet’s routine is followed closely for an easy and stress-free transition. I send daily photo and video updates so you always know how your pet is doing, and I’m especially sensitive to owners who are very attached to their animals — I’m here to help you feel confident and connected while you're away. Before any booking, I like to learn more about your pet’s specific needs: What is their feeding schedule? How often do they need potty breaks? Do they require daily walks, playtime, or specific care routines? Are there any medical needs, anxiety triggers, or behavior quirks I should know about? My goal is to create a home-away-from-home experience where your dog or cat feels safe, relaxed, and truly cared for. I welcome all types of pets — young, old, shy, energetic, or somewhere in between — and I'm committed to giving each one the love and attention they deserve. Let’s chat about how I can make your pet’s time away from you as smooth and comfortable as possible! Pet care is part of my daily life. I work from home and have a flexible schedule, so I’m with the pets 24/7 — they’re never left alone and always get constant attention, love, and care. Whether it’s daily walks, potty breaks, medication, or just play and snuggles, I easily build their routines into my day. I’ve grown up around animals, volunteered at a shelter for 3 years, and my mom’s a veterinarian — so caring for pets is second nature to me. Making animals feel safe, happy, and at home is what I do every day! In my home, pets are treated like family. I’m with them at all times — they’re never left alone — and they receive constant attention, love, and personalized care. I follow their usual routines closely, including feeding, potty breaks, walks, and any special needs they may have. I keep pet parents updated daily with photos, videos, and messages so they always feel connected. When caring for pets in a client’s home, I do my best to maintain their normal routine and comfort. I’m punctual, respectful of your space, and committed to making sure your pet feels safe and secure in their familiar environment. Whether it's boarding, drop-ins, or walks, I always provide calm, reliable, and attentive care.
Winchester dog parents share their Rover experiences
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.

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 .

How Rover works

1. Search
Read verified reviews and choose a dog walker who’s a great match for you and your dog
2. Meet & Greet
Meet either virtually or in-person with a walker to discuss the level of care needed for your dog
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per walk for dog walking in Winchester is $20
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 dog walker has to cancel, we’ll work with you to find a new walker.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winchester average 3 repeat dog walking clients
Dog Walking FAQs
Frequently asked questions about Rover
Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Winchester on Rover as of Jun 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Jun 2026, there are 2,307 dog walkers in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 86% of Winchester dog walkers respond in under an hour.
Dog walkers in Winchester have an average of 16 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Winchester.
You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:
- Start and stop times
- A map of their walk with total distance
- Pee, poo, food, and water breaks
- Cute photos and a personalized note
There are 2,307 dog walkers in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 93% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.
Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.










