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.
“Ashlee is just amazing!!! From taking the time to meet up and get to know the dogs. To how professional she was in asking questions about the care of our babies, as well as our home. She has a lovely disposition, she is so kind and gentle with our babies. She made the experience seamless. We are extremely lucky to have found someone so dedicated and caring. We will always think of actually when we need help again. We highly appreciate her and recommend her services.”
“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.”
“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!”
“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!”
“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!”
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.
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
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!
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: 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 have previously worked as a dog bather and kennel attendant. I’ve grown up with dogs and am currently helping care for my family’s elderly dog. I have my own cat and snake! I love all animals so much! I have worked with old dogs, puppies, dog aggressive dogs, high energy dogs, blind dogs, dogs that require medicine administrated to them, and scared and shy dogs. I know I can ensure your pet will be comfortable and safe! Im open to any availability! My schedule is flexible and im willing to make things work. I make jewelry, so i like to fit pet care within my schedule! I will be sure to have an understanding for each pet individually as just like humans they are all unique in their own way. I will provide open communication with pet parents and care for them as if they were one of mine!
“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!”
“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: 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: Hi! I’m Jennifer I am a gentle, calm, nurturing sitter who specializes in senior and small dogs. I understand that older pups need patience, softness, slow pacing, and lots of love. I have a naturally peaceful energy, and I’m very tuned-in to dogs who need extra comfort, routine, meds, or mobility care. I offer in-home visits, walks, and overnight house-sitting so your dog can stay in their cozy, familiar environment. Your home and your pet will be treated with care, respect, and attention. I’m a mom and a naturally gentle caregiver, so I always keep safety, stability, and routine first. I love snuggly dogs, mellow seniors, sweet small dogs, and pups who just need companionship and reassurance while their humans are away. Senior dog care (slow walks, mobility support, bedding changes, gentle routines) Small dog care (snuggles, supervised time, potty breaks, consistent comfort) Drop-in visits (feeding, meds, potty breaks, companionship) Dog walking Overnight house-sitting (your dog sleeps peacefully at home) Light home tasks: mail, plants, tidying pet areas Regular updates, photos, and communication Pet care fits naturally into my daily rhythm because I already keep a calm, structured home. I’m a very routine-oriented person. Mornings and evenings are dedicated to care, feeding, and gentle companionship. I build my schedule around being present, checking in often, and moving at each dog’s pace. Since I’m home often for school and taking care of my family, I have plenty of time for drop-ins, walks, and extended visits. Caring for animals feels like an easy, natural part of my day, something that brings peace, not stress. Also, my son loves animals just as much as I do and is school age, so while he is learning at school, I am caring for your fur babies. I care for pets in my clients’ homes by keeping everything calm, gentle, and consistent with the routine they already know. Senior dogs and small dogs especially need a steady, loving presence. So I move slowly, speak softly, and offer lots of reassurance and companionship. I follow your instructions closely, including: feeding times and amounts walk schedules medication routines mobility support (slow walks, gentle lifting if needed) bedtime rituals and comfort preferences My goal is for your dog to feel safe, understood, and relaxed the entire time you’re away. While staying in your home, I also: keep everything clean and tidy respect your space and privacy water plants, bring in mail, and maintain the space Give frequent photo updates Whether it’s drop-in visits or overnight stays, your dog will have a warm, patient caretaker, and your home will be trusted and protected.
The median cost per walk for dog walking in Winchester is $20
Dog parents share their Rover experiences - Winchester
I feel very lucky to have found Hannah. She was amazing with my dog and I genuinely looked forward to reading her updates every day. She did such a great job using the app—lots of photos, tracking their walks, meals, poops and pees, and writing detailed updates about their time together. It gave me so much peace of mind knowing my pup was in such good hands. I would happily book with Hannah again.
Brianna was great! She was on time for the walk, she also helped me get my rover profile set up and even though I only needed the one walk. She still honored the 20$ dollar coupon and provided the walk for me and she has been the first person willing to do that. I have had seen other rover coupons on social media and because I wasn't requiring anything more then a walk or two the refused to allow the use of the coupon. She took very good care of my dog Candy and followed my instructions thoroughly. She also was very easy to communicate with just be forth coming about you communication expectations. If you are wanting regular updates Brianna will provide them I just gave her my personal number and requested to be updated during pick up and drop off of Candy. Thank you so much Brianna! I will absolutely reach out again when I need another service for candy!
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog walking
2. Meet & Greet
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 near you
Select a filter and find qualifying Winchester sitters!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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