Dog Walking Winchester

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

End
Search

Over 65
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.

1 / 1
Sitter Profile Image: Tanika L.
Verified Enhanced Background Check
Tanika L.
from
$18
per walk
5.0 out of 5 stars
16 reviews
4 repeat clients
12 years of experience
Richmond, KY, 40475

Tanika is the best! She was able to take care of my little fur baby LAST MINUTE and did SUCH a great job!! I have a regular Rover or I'd be asking for her services every day!

Profile image
Dave W.
Sitter Profile Image: Kayla C.
Verified Enhanced Background Check
Kayla C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
161 reviews
66 repeat clients
5 years of experience
Lexington, KY, 40509

Kayla was great! I’ve tried rover before and my dog doesn’t do good with separation anxiety at other peoples houses. So when I went in my last trip I had Kayla come walk her three times a day as well as feed and water her. My pup did great no accidents and was happy to be in her home. Will def be going this route for vacations in the future

Profile image
Mckenzie B.
Sitter Profile Image: Isabella L.
Verified Enhanced Background Check
Isabella L.
from
$50
per walk
5.0 out of 5 stars
18 reviews
7 repeat clients
5 years of experience
Winchester, KY, 40391

Isabella was great. Our dog was happy to see her and she treated our dog like her own. I highly recommend Isabella!

Profile image
Rodney R.
Sitter Profile Image: Maria L.
Verified Background Check
Maria L.
from
$35
per walk
4.6 out of 5 stars
7 reviews
7 repeat clients
15 years of experience
Winchester, KY, 40391

We are so blessed to have found Maria to walk our dog, Aria. She's been walking Aria 3-4 times a week for a year now, and she loves Aria like she's her own. I could not speak more highly of her. We love, Maria!

Profile image
Ashley S.
Sitter Profile Image: Debra R.
Verified Enhanced Background Check
Debra R.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
15 reviews
3 repeat clients
40 years of experience
WINCHESTER, KY, 40391

About: I have experience with dogs and cats. My pets are treated like family. I am a retired nurse and I will do my very best to treat your pet and home with the utmost care. I am retired from nursing but I’m looking for something to keep busy and to help others. I’m available 95% of the time. I am reliable and can be trusted to take care of your fur baby. I will follow your instructions exactly to care for your beloved pet in your home. I will treat your pet and home with respect and care.

Sitter Profile Image: Laura S.
Verified Background Check
Laura S.
from
$25
per walk
5.0 out of 5 stars
14 reviews
6 repeat clients
10 years of experience
Winchester, KY, 40391

About: I have always been passionate about helping and caring for people and animals. I have care experience with many breeds and types of animals, including dogs, cats, birds, rodents, reptiles, and horses. I adore dogs especially — their friendliness, loyalty, and energetic demeanor is contagious, and I love them so much for it! My dream is to rescue animals and help to find their forever homes. I will love and care for your pet(s) like my own. As for more about me, I am originally from Kentucky, and I studied music, specifically opera, all throughout college. I am a singer, actress, model, chef-in-the-making, fitness guru, social media influencer, artist, writer, and much more. I enjoy meeting new people and animals, and my greatest goal in life is to help as many others, human and animal, as I possibly can! I am able to check in as early at 9am, and as late as 9pm. I often have my children with me, and they either wait in the car or join us for walks in their stroller. I like to gather as much information from you as possible so that I can recreate your pet’s daily routine while you’re away! I enjoy giving animals the best, most comfortable and familiar experience as possible.

Sitter Profile Image: Ebony H.
Verified Background Check
Ebony H.
from
$20
per walk
5.0 out of 5 stars
45 reviews
3 repeat clients
25 years of experience
Winchester, KY, 40391

About: Families book with me for loving, family-style care, frequent photo updates (if desired), and the peace of mind that comes from working with a sitter trusted by repeat clients since 2021. 🐶 I simply love dogs. They are truly my passion. 🐾 Caring for them isn’t just something I do, it’s something that fills my heart. 💚 I have a special love and deep experience with breeds such as English Bulldogs, French Bulldogs, Lhasa Apsos, Shih Tzus, Shorkies, Greyhounds, Cavalier King Charles Spaniels, and Bernedoodles, but I genuinely enjoy caring for all breeds and personalities. Every pup deserves to feel safe, adored, and understood. Dogs have been a part of my life for as long as I can remember. While I can’t be a full-time fur mama to them all, dog sitting allows me to pour love into as many pups as possible and I wouldn’t trade that for anything. It has been such a blessing to learn and care for new breeds through my bookings. Each dog I welcome into my home deepens my knowledge, strengthens my skills, and grows my love for dogs even more. What truly sets me apart is the family experience I provide. When your dog stays with me, they aren’t just “watched”—they become part of our home. While your family is away, your fur baby enjoys a warm, loving, family-style environment filled with cuddles, attention, and genuine connection. I happily send plenty of photo updates (if desired) so you can relax knowing your pup is safe, happy, and well-loved. My family loves dogs too, and on occasion, trusted family members may stop by simply to meet my furry clients and share a few extra cuddles (not to assist with care), but purely because they enjoy loving on dogs. 🐶 Some of my favorite repeat clients even get to travel with me, including family visits and store outings (photos available!). Your dog gets real-life experiences, companionship, and enrichment—not just a place to stay. Over the years, I have lovingly been a full-time fur mom to up to three dogs at the same time, gaining daily, hands-on experience managing multiple dogs under one roof. Currently, my home includes Khaleesi, my sweet English Bulldog girl. I also carry deep love for my Lhasa Apso, who crossed the rainbow bridge in August 2023 🌈. My Shorkie was lovingly rehomed with an older family member to provide emotional support, and while she no longer lives in my home, she remains part of my extended family story. I’m also what I proudly call a “Mid-Woof” 🐶—I have independently and successfully delivered 4 litters of puppies in my home and have personally whelped, nursed, and raised two litters until 4–8 weeks of age before helping them find their forever homes. I understand canine behavior, comfort, and care on a deeper level than most. I will love on your fur baby as if they were my own. Bulldogs, in particular, require a special level of patience, knowledge, and care and if you’re a bulldog parent, I’m absolutely your girl. (Bulldog hugs are always welcome 😉) I’m proud to share that I have 10+ repeat clients, including several families who have trusted me with their fur babies consistently since 2021—relationships built on love, reliability, and peace of mind. I look forward to being your dog’s Bonus Mom while you’re away. Let’s get your pup booked, loved, and spoiled! 🐾💕 I work in an office Monday–Friday but return home on lunch breaks for potty breaks and check-ins. After working from home for seven years, I’ve adjusted my availability while remaining intentional and reliable. I’m a mom to young children under 10 who are gentle, respectful, and great with dogs 🥰. I’m available for daytime drop-in visits, and on weekends (when in town) I’m fully available for dog sitting in your home, my home, or for additional check-ins. I have plenty of grassy space where I live in a dog friendly neighborhood. I also have a fur baby to keep your dogs company if needed for service in my home. I have a dog area set up in my home. We also travel to dog parks when weather permits, if your dog needs activities, we will go on walks and even to our favorite dog park!

Sitter Profile Image: Maggie M.
Verified Enhanced Background Check
Maggie M.
from
$15
per walk
4 years of experience
Lexington, KY, 40509

About: I am a Licensed Veterinary Technician, worked with small animals and now do mostly large animals. I have grown up with dogs my entire life. I love your pets and would love to help !! I currently work for Lexington Equine Medical and it is becoming our off season, so I am starting to free up in the afternoons! I can come whenever I am off and communicate that with you and do whatever is needed for you and your pet ! I’ve grown up with dogs my entire life , and that really persuaded me to be the Licensed Vet tech I am today. I love being around animals and I care deeply for them no matter to what extent ! I also can’t have a dog where i am living now so kind of get the best of both worlds getting to bond with your pet :)

Sitter Profile Image: Sara P.
Verified Enhanced Background Check
Sara P.
from
$20
per walk
5.0 out of 5 stars
4 reviews
4 years of experience
Lexington, KY, 40516

About: Growing up, I took the most responsibility for caring for our family German Shepherd. Her name was Daisy and I was responsible for teaching her how to sit and stay, we went on daily walks when the weather was nice and even though she was considered a family pet she was mine. I do not have training skills past basic household tricks but I have plenty of love to give. I don’t have much of a set routine at work. I am technically full-time, but my schedule varies drastically from week to week. This is why I have my booking two weeks in advance so I can plan accordingly. Other than my job, I am a homebody. I do love being outside and going for walks/hikes when the weather is nicer. I’m very courteous and if you leave specific instructions for your home, I will follow them to a T. As for my own home, I have two cats that have free range over every room. I have no plants at all (let alone anything that would be dangerous for animals), a water fountain that’s plugged up for continuous running water, and three litter boxes throughout the home. I am more equipped for cats when it comes to toys, scratching post/cat trees and treats.

Sitter Profile Image: Casey C.
Verified Enhanced Background Check
Casey C.
from
$13
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
4 years of experience
Paris, KY, 40361

About: Hi, My name is Casey and I would love to be able to take care of your animals. I love all kinds of animals! I can provide any of the services listed. I am not new to taking care of animals and I have house sit for people before. I work full-time on this app. If you have any questions please feel free to message me! I have two cats and two dogs at home so I spend plenty of time with all of them by playing with them, feeding them, showing them new activities, and spoiling them! We have a fenced in back yard. I always listen to instruction's so anything your pet needs I will be happy to help with! Always looking forward to meeting new animals!

Sitter Profile Image: Alysha K.
Verified Enhanced Background Check
Alysha K.
from
$15
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
12 years of experience
Lexington, KY, 40509

About: I am pretty flexible around my work schedule with caring for dogs, I can find a way to make sure your dogs are a top priority in my daily schedule. Since my work schedule does range, I will keep my availability updated. I have always taken care of my own dogs and other people’s almost my whole life since I was a preteen. I absolutely adore getting to know other dogs and giving/receiving love from them. I’ve been training with dogs since I was 11 years old in basic manners, tricks, and agility, so I am experienced in training puppies and younger dogs. I am always up for learning more about other dogs and their personalities as well. They are such intriguing and beautiful animals. I make sure to walk dogs before and after work. Dog park a few times a week. (If that’s in their routine) And lots of cuddle time! Brushing and brushing teeth are weekly tasks normally. I ask for the pets’ normal routine. This way, it is less stressful on them that their routine doesn’t change as much with their person/people gone.

Sitter Profile Image: Chelsea C.
Verified Enhanced Background Check
Chelsea C.
from
$13
per walk
6 years of experience
Winchester, KY, 40391

About: I am attentive, dependable, and experienced in providing compassionate care while closely monitoring health and behavior. I have cared for dogs and cats of various ages, sizes, and temperaments, including energetic puppies, senior pets, and those requiring medication. I understand that every pet has unique needs, and I strive to keep their routine consistent, reduce stress, and provide plenty of attention, exercise, and affection while you're away. My goal is for both you and your pet to feel comfortable, confident, and cared for throughout the entire experience. Pet care fits well into my weekly routine, allowing me to provide dependable care, walks, drop-in visits, and quality time with your pets. I maintain a flexible schedule and prioritize clear communication, including updates and photos so you can feel connected to your pet while you're away. I am committed to being punctual, reliable, and ensuring your pet receives the attention and care they deserve. Your pet's safety and well-being are my top priorities. I follow all care instructions carefully, including feeding schedules, medication administration, exercise needs, and household routines. During visits, I ensure pets have a safe environment, fresh water, and plenty of attention. I treat every client's home with respect and maintain a clean, secure space while caring for their pets. I provide regular updates and photos so you can have peace of mind knowing your pet is safe, happy, and receiving attentive care.

Sitter Profile Image: Danielle J.
Verified Background Check
Danielle J.
from
$30
per walk
5 years of experience
Winchester, KY, 40391

About: Overs and make sure it gets the proper exercise. the last 5 years I have taken care of dogs of all shapes and sizes. I have lots of energy which is perfect for keeping up with a dog. I would give your dog the best care and my full attention. I would take your dog for plenty of walks and make sure it gets the proper exercise. I will also make sure you come home to a clean house.

Sitter Profile Image: Sonya B.
Verified Background Check
Sonya B.
from
$35
per walk
4.7 out of 5 stars
31 reviews
5 repeat clients
15 years of experience
Winchester, KY, 40391

My dog was tired out when I got home after a long day.

Profile image
Kim M.
Sitter Profile Image: Pam D.
Verified Enhanced Background Check
Pam D.
from
$25
per walk
1 repeat client
10 years of experience
Winchester, KY, 40391

About: I have been dogsitting for over 5 years. The clients I have worked for I have done overnight stays, dog walks, and day sitting for up to 8-10 hours. I do have one dog I sit for that doesn’t do walks so I adjust to what the clients needs. On overnight stays, I do clean up and bring in mail/ newspaper if the clients ask. I am a big animal lover so your dog/ cat will get lots of love. I do have a clients that likes to receive pictures during my stay. The dog will get plenty of exercise and playtime. Also I am flexible and very reliable. I can provide references of my regulars if needed and their type of dog. I enjoy providing lots of fun and love. I am flexible and reliable. I am able to meet to whatever the client might need. I am available whatever day and time. I do my best to meet the needs of the client. I haven’t cared for other animals in my home besides my own. When I go to someone’s residence, I follow what the owner normally does. I am usually left instructions to follow.

Sitter Profile Image: Miranda K.
Verified Enhanced Background Check
Miranda K.
from
$15
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Winchester, KY, 40391

About: I have had all kinds of pets of my own as well as when I was child. Love them all and very willing to care for you puppies! I am a work from home mom with two dogs of my own. Can come during my lunch breaks and in the evenings after work during the week and the weekends are typically free for me We love on our pets here they sleep in our beds with us. We have 2 pugs and they are the best thing ever! I have a soft spot for dogs particularly.

Sitter Profile Image: Olivia C.
Verified Background Check
Olivia C.
from
$16
per walk
5.0 out of 5 stars
22 reviews
9 repeat clients
15 years of experience
Lexington, KY, 40509

About: Hey there! I am a pet/animal lover and enthusiast. I would have all the animals in the world if I could. I currently have 1 dog, Kash, and 1 cat, Darla Jean. Animals and caring for them are my life! Here’s my why: My grandmother lost her husband at a young age. She never dated again. She took in dogs and taking care of those dogs became her life purpose. Growing up, I would always want to visit my grandmother so that I could stay up all night with her and take care of the dogs. It became our thing. I feel that I am now living out my grandmother’s purpose by fulfilling my own purpose in giving unconditional love and care to any animal that crosses my path, just as she would have done. I love animals, and quite honestly, more than people, haha! I look forward to meeting, loving on, and caring for your fur baby as if they are my own. ❤️🐾 I am a special education teacher full time, but my toddler and myself love to show unconditional love to animals by taking care of them like they are our own. I get to do what I love as a part time “side hustle” plus also show my little boy of my own how to treat and care for animals plus teaching some responsibility! I’m available evenings, most weekends, and most holidays/ school breaks. It says on my profile “no children in the home,” but since I started Rover, I have had a baby and there is a 2 year old in the home. I tried to edit that info but literally cannot find it anywhere. Just wanted to make sure that was said though. Anyway, I’ll care for your pet as if they were my own child. I like to meet with my clients face to face first so that I can get to know not only their fur baby, but their expectations in caring for their pet. I’m a great listener and follower of directions, so if you tell me exactly what you need, I will do my very best to make that happen.

Sitter Profile Image: Joseph M.
Verified Background Check
Joseph M.
from
$20
per walk
4.9 out of 5 stars
116 reviews
48 repeat clients
7 years of experience
Lexington, KY, 40509

Joseph is the most conscientious and dedicated dog caregiver. Knowing he is walking, watching and playing with my animal makes me worry less about being away.

Profile image
Lynn S.
Sitter Profile Image: Courtney S.
Verified Background Check
Courtney S.
from
$20
per walk
10 years of experience
Lexington, KY, 40515

About: I am a certified professional dog trainer and was a veterinary assistant for over 8 years. I have over a decade of experience caring for animals large and small. I have ample experience caring for pets with mobility issues, incontinence, kidney disease, diabetes, anxiety, or other illnesses. I can provide gold standard care regardless of your pet's needs- including oral, topical, or injectable medications, subcutaneous fluid therapy, or just being a patient and calm friend to a fearful friend. I love and care for dogs and cats equally! I currently work a full-time 9-to-5 but have a somewhat flexible schedule within those hours. Early mornings, lunch breaks, evenings, nighttime checks, and weekends are all available options. If taking your pet out of the house, I like to have a fit check of your leash/harness or collar setup first. If your pet is known to be a "houdini" who can escape their gear, I may recommend alternatives and can help you with fitting your pet appropriately and/or bring a second form of containment with me (such as a slip leash used at vet offices) to ensure your pet's safety.

Sitter Profile Image: Shelby V.
Verified Background Check
Shelby V.
from
$20
per walk
1 repeat client
16 years of experience
Winchester, KY, 40391

About: I’ve been around animals all my life and I’m always the friend who gets asked to watch the dogs while the owners are out of town. I’m also a college student who moved away from my dogs so it’d be nice to see some furry friends still! I might even teach them a new trick or two! I am currently unemployed so Rover is a great option for me right now while I’m figuring out what I want to do in the future. Therefore I’m available 24/7 and would love to help take care of your animals! I’ll do whatever it takes to make sure your pet(s) still have a fun time while their human is away! I’ll treat them as if they were my own!

1 / 1
View more

The median cost per walk for dog walking in Winchester is $18

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. 1. Search

    Browse profiles of walkers near you who offer dog walking
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 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 4
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 $18.87 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 705 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:

  • 100% of walkers can help with special care needs
  • 98% 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge