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.

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Sitter Profile Image: Debra R.
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Debra R.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 9 reviews
2 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: Maria L.
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Maria L.
from
$25
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!”

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Ashley S.
Sitter Profile Image: Ebony H.
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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: Dakota B.
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Dakota B.
from
$20
per walk
8 years of experience
Winchester, KY, 40391

About: I’ve have taken care of pets since I was 8, helped them when they were pregnant and giving birth and made sure they were healthy I’m currently not working, I will have plenty of time to take care of these cute animals and take them on great walks and play dates I have two friendly dogs that love playing with other dogs I have crates if they are needed and a backyard for them to play.

Sitter Profile Image: Chelsea D.
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Chelsea D.
from
$15
per walk
5.0 out of 5 stars
• 32 reviews
8 repeat clients
15 years of experience
Winchester, KY, 40391

“Chelsea was great. She greeted our pup with enthusiasm and took the time to let her sniff which to a Beagle is everything.”

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Jennifer R.
Sitter Profile Image: Rubes A.
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Rubes A.
from
$17
per walk
5.0 out of 5 stars
• 109 reviews
39 repeat clients
10 years of experience
Lexington, KY, 40509

“Rubes was great at communicating and sending updates on our high energy GSP. We found her to be very flexible and reliable.”

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Courtney L.
Sitter Profile Image: Michele R.
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Michele R.
from
$15
per walk
54 years of experience
Lexington, KY, 40509

About: I have taken care of both dogs and cats since I was 10. Nieghbors, families and friends have always relied on my support. I am able to feed, walk and bathe as necessary your pet(s). I am familiar with working with pets with diabetes and thyroid conditions. I am retired and available most days mornings and night during the week and weekends, providing 4-6hr breaks, so there is minimal daily. I would be able to walk pets also on an as need basis as well! I believe a pet is most comfortable in their own home environment, especially if older. I am willing to travel twice per day and stay overnight if easier to care every 4-6 hrs.

Sitter Profile Image: SaĂ­ra O.
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SaĂ­ra O.
from
$20
per walk
4.7 out of 5 stars
• 19 reviews
6 repeat clients
15 years of experience
Eastland Park-Dixie Plantation, LEXINGTON, KY, 40505

“Saíra is fantastic! She always goes above and beyond when taking care of my boys. I highly recommend for all your pet sitting needs.”

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Tyler T.
Sitter Profile Image: Tanika L.
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Tanika L.
from
$18
per walk
5.0 out of 5 stars
• 11 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!”

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Dave W.
Sitter Profile Image: Sara P.
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Sara P.
from
$20
per walk
5.0 out of 5 stars
• 3 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: 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: 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.”

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Kim M.
Sitter Profile Image: Laura S.
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Laura S.
from
$25
per walk
5.0 out of 5 stars
• 12 reviews
5 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: 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!

Sitter Profile Image: Kayla C.
Verified Enhanced Background Check
Kayla C.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
• 149 reviews
65 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”

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Mckenzie B.
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: 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: 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: Finnley R.
Verified Background Check
Finnley R.
from
$15
per walk
5.0 out of 5 stars
• 120 reviews
19 repeat clients
7 years of experience
Richmond, KY, 40475

“Thanks again!!”

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Chris M.
Sitter Profile Image: Eslam S.
Verified Enhanced Background Check
Eslam S.
from
$30
per walk
5.0 out of 5 stars
• 2 reviews
1 repeat client
10 years of experience
Lexington, KY, 40509

About: Since I was a child, I've been surrounded by pets. I grew up with two dogs and two cats, so I'm used to being around animals. I've worked with a variety of dogs, and my friends and family trust me to look after their pets! I have a fairly flexible schedule because I have some free time throughout the day. As a result, I can provide services early, midday, and late. I understand that some plans must be made at the last minute, so I am willing to accept last-minute bookings. Just let me know, and I'll do my best to work with you! I currently do not have any pets, so when I need to house sit your pet, they will be safe because they are the only pets there

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Over 34
pet parents in Winchester have booked dog walking

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The median cost per walk for dog walking in Winchester is $17

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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 Feb 2026 was about $17 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.

If you’re searching for a Winchester dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Feb 2026, there are 655 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, 82% of Winchester dog walkers respond in under an hour.

Dog walkers in Winchester have an average of 14 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 655 dog walkers in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 96% 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.