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

Over 121 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.

“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!”

“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! ☺️💖”

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.
“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: Experienced in providing loving, reliable pet care with a strong focus on safety, comfort, and individualized attention, ensuring every pet feels secure, happy, and well cared for. I prioritize plenty of playtime, gentle affection, and engaging interaction tailored to each pet’s personality and needs, so they feel right at home while you’re away. I have a flexible routine that allows me to give pets plenty of attention, walks, playtime, and care throughout the day. I’m reliable with schedules and make sure every pet feels safe, happy, and loved I care for pets in my home and/or my client’s home by following their normal routine as closely as possible, including feeding schedules, walks, playtime, and any special instructions. I make sure they get plenty of attention, comfort, and supervision so they feel safe, relaxed, and well cared for while their owner is away.
About: I have hands-on experience caring for dogs through friends and family, including overnight stays, feeding, walks, playtime, potty breaks, and keeping them company. I’m comfortable following each pet’s routine and paying attention to their individual needs. I’m patient, responsible, and attentive, and I treat every pet with the same care and attention I would want for my own. I especially enjoy getting to know each pet’s personality and making sure they feel comfortable and loved while their owner is away. I’m currently available for pet care with a flexible schedule. I’ll be starting nursing hospital rotations in October, which will be 12-hour rotations once or twice a week. I’ll keep my availability updated around my school schedule and am happy to work with you to find a schedule that fits your pet’s routine. 🐾 Your pet’s safety, comfort, and happiness are my top priorities. I carefully follow each owner’s instructions and make sure pets have a clean, comfortable, and safe environment. I’ll keep their normal routine as consistent as possible, including meals, walks, medications, potty breaks, and other care they need. I also pay close attention to their behavior and energy level so I can make sure they’re comfortable throughout their stay.I want you to feel confident knowing your pet is in caring and responsible hands. 🐾💕
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 grew up with animals from dogs to guinea pigs. I have experience with owning and caring for a pet. I have the space and recourses to board or pet sit. I would love to care for your fur baby. I am free during day all week. I have an open schedule Saturday, Sunday and Monday. I have time to care for pets whether it is giving scheduled medications or just to be walked and played with. My backyard is completely closed with concrete wall. I do allow pets in my house. The pet will have easy access in and out of the house.

About: I’ve always had dogs growing up and was the primary caretaker. I’ve pet sat for many many families as well. I primarily take care of dogs and cats, but I do know how to care for hamsters, rats, and bunnies :) I work part time as a server, so i’m able to have flexibility to have mostly any schedule you'll need. Animals have always been centered in my life! I like to keep your pet entertained and stimulated as much as I can, especially if it’s just a drop in. I will make sure they don’t get into stuff they shouldn’t since i’ll be supervising them all day.
About: I have been pet sitting since I was 13 years old. Sometimes doing it on my own for neighbors and sometimes helping my grandma who has done it full time for ten years. I am a part time student at CSN but I am available seven days a week for house sitting, walks and drop in visits. . I will walk your dogs regularly and make sure your pets are fed and given plenty of attention so they are happy and you don’t have to worry about them while you’re away.

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: 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.
“I appreciate Anna's care and attention to Cooper. She went above and beyond in spending time with him and providing the needed care. Will deficit request her for future needs.”

“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: I have been around animals all my life since childhood and up to my adult years . I have taken care of dogs, cats , hamster, rabbits and guinea pigs. I’m currently working part time and have open availability during the week and on weekends. I would love the opportunity to take care of pets since I love animals. I have a fenced yard and plenty of space inside. My cats stay inside and have plenty of room to roam around. My home is safe and quiet. My small dog is walked daily in my small community.
About: I love dogs/animals. Have grown up on a farm and working with all kinds of animals including cats, reptiles, fish, horses, cows etc. My extended family in Australia are vets and work at a zoo so very experienced and exposed to all different scenarios. I am studying to be a doctor and work part time at night so am flexible for pet sitting requirements. I live by the strip and happy to travel to check on your fur babies with constant communication. I own a pet friendly condo set up for those overnight stays, crates, bowls, toys and love on hand. I work at night part time and studying to become a doctor online so am very flexible on care requirements for you and your fur babies. I can do pop in visits and will communicate often. I am also open to odd hour visits such as early hours of the morning or late night as being a shift worker i understand some dogs schedules are adjusted to owners in the industry just like me. i understand our pets are fur babies and safety and trust is vital. I understand when in unfamiliar environments it is sometimes difficult for our fur family to navigate and pride myself in making it as comfortable as possible for them.
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! 💕🐾

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.
How to book dog walking

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 of Dog Walking in Winchester is $17 per walk as of October 2026. Most bookings cost between $13 and $22 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 2,387 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 bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include , the total walk time and distance, and any pee or poop breaks recorded by the walker.
The route map lets you review where your dog was walked in Winchester after the booking. It is not live GPS tracking.
Have specific details you would like included? Message your dog walker in the app before the 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 , 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 .
Yes, you can find walkers who have experience with handling special pet needs in Winchester. On Rover:
- 91% of walkers can help with special care needs
- 93% can help with giving oral medications or injections
- 97% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first .
walkers on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.








