Dog Walking Winchester

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Over 21
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.

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Sitter Profile Image: Emily P.
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Emily P.
from
$15
per walk
5.0 out of 5 stars
• 7 reviews
2 repeat clients
15 years of experience
Ballwin, MO, 63021

About: I’m an experienced dog owner with years of hands-on care for dogs of different breeds, sizes, energy levels, and personalities. I currently care for a cat (My sweet Sassy) and multiple dogs, including German Shepherds, Belgian Malinois and my small breed Corgi Beagle mix Luke-y so I’m very comfortable with large, active, and high-energy breeds. I’m experienced with structured walks, exercise, feeding routines, basic commands, medication schedules, and giving each dog individualized attention. I understand that every pet has their own personality and routine, and I will treat your babies with the same patience, attentiveness, and love that I give my loves. I’m currently in the military but love nothing more than hanging out with my babies - and more babies we meet the greater! :) My babies are such a huge part of my everyday routine, so adding another pup to the mix comes pretty naturally to me. We’re big on walks, outside time, playing fetch and tug and just hanging out on the couch. I’m used to planning my day around my cat and dogs and making sure each gets the attention and exercise they need. I have multiple dogs of my own, so I know every dog is different and has their own personality and needs. I’m very comfortable with XL / big dogs and high-energy breeds, but I’m also big on keeping everyone safe and structured. I’ll follow whatever routine you have for your pup and treat them like I would want someone to treat mine.

Sitter Profile Image: Laura D.
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Laura D.
from
$15
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
25 years of experience
Ballwin, MO, 63011

About: Hi! I’m a local mom, animal lover, and lifelong dog enthusiast! 🐾❤️ Our family sadly lost our sweet dog this summer, and while our hearts aren’t quite ready to welcome a new puppy of our own, we have so much love left to give! I would absolutely love the opportunity to care for yours! I’m offering dog walking, pet sitting, and check-in services for busy families, working professionals, or anyone who needs an extra helping hand with their furry family members. Whether your pup needs a neighborhood walk, a potty break, some playtime, or a loving place to stay while you’re away, I’d love to help! I know firsthand that pets are family, and I promise to treat yours with the same love, attention, and care that I would my own. I can’t wait to meet your four-legged family members! 🐶💕 I have a very flexible schedule for the most part. I am a real estate agent and a mom to twin boys who are in school full time. I can easily pop over to your home or have your dog to our house as well. My yard is almost completely fenced in except for our driveway. I’m happy to take your dog on walks as well. I am happy to let your dog run free inside at our home or crate. Whatever makes you feel comfortable.

Sitter Profile Image: Jennifer B.
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Jennifer B.
from
$20
per walk
5.0 out of 5 stars
• 3 reviews
2 repeat clients
20 years of experience
Chesterfield, MO, 63017

“Jennifer was awesome! Reliable, friendly, and very caring for our Riley. We would recommend her highly!”

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Lenny S.
Sitter Profile Image: Amy H.
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Amy H.
from
$18
per walk
5.0 out of 5 stars
• 2 reviews
10 years of experience
Central West End, Ballwin, MO, 63011

About: I’ve had cats my whole life and love everything about them! I’ve cared for kittens, adults, seniors, and multiple pet households. I have experience with post-op care, cat introductions, and indoor/outdoor cats. I also have experience taking care of young and senior dogs, including administering medication and interacting with cats. Housesitting - I can’t be there 24 hours a day because I have my own pets, but we can discuss how much I need to be away. I work full time from home, mostly available evenings and weekends, daytime if my schedule allows. I’m a night owl so late night visits are okay! I go at your pet’s pace and provide a safe, loving environment so they gain my trust. I go by their usual routine/ habits as not disrupt their routine.

Sitter Profile Image: Brody Z.
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Brody Z.
from
$16
per walk
5.0 out of 5 stars
• 7 reviews
3 repeat clients
12 years of experience
Ballwin, MO, 63021

“Replies promptly, sends photo, converse as well, and as a genuine love for dogs!”

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Michelle K.
Sitter Profile Image: Callie L.
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Callie L.
from
$25
per walk
5.0 out of 5 stars
• 106 reviews
32 repeat clients
10 years of experience
Chesterfield, MO, 63017

“Our first experience with Rover was pretty rough so it has been several years since I’ve used it…but our sitter graduated and is heading out of state for college so I started looking for another sitter. Callie has done a great job, and has been punctual, thorough, and most importantly she is really good to our fur babies. I’ll gladly become a repeat client, thanks very much for taking exceptional care of our doggies, Callie.”

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Darrell And Katie C.
Sitter Profile Image: Christine H.
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Christine H.
from
$15
per walk
5.0 out of 5 stars
• 9 reviews
1 repeat client
18 years of experience
Apt 5, MO, 63122

About: I have been taking care of dogs my whole life. My sweet Charlie passed in 2024 and to fill the void, I am now taking care of other people's pets. I am able to administer meds or whatever is needed. I work from home, so I am very flexible in my schedule. I can go to your house for boarding, or your pets can stay here. I love having toys around for the pups to play with. Very pet friendly environment. I do not have any other pets in my home. I only have one booking at a time. I want to make sure to give your fur babies all the love they deserve. Its only me at my home. My son is in college.

Sitter Profile Image: Shalini B.
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Shalini B.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
10 years of experience
Manchester, MO, 63088

“Shalini did a great job with walking our dog while I was out of town! Appreciated her communication and how thoroughly she prepared to ensure both she and our dog would be comfortable.”

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Alice L.
Sitter Profile Image: Liana V.
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Liana V.
from
$25
per walk
5.0 out of 5 stars
• 35 reviews
6 repeat clients
14 years of experience
Ellisville, MO, 63021

About: I have experience pet sitting, I’ve worked at multiple clinics, volunteered at shelters, etc. I have experience with large, small, and exotic animals. Thank you!! I am currently working part time so I have plenty of time to play with your furry friends! My schedule is regular but flexible. I have time everyday to take care of your family’s needs!! I have learned a lot in the field and in my classes about Veterinary medicine and I have always strived to pay attention to details and give my very best to each client and their loved one(s).

Sitter Profile Image: Shannon R.
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Shannon R.
from
$15
per walk
5.0 out of 5 stars
• 3 reviews
20 years of experience
Ballwin, MO, 63021

About: I have two dogs in my own and have taken care of numerous different breeds in my neighborhood, along with family and friends. I enjoy taking walks and enjoy spending time with all types of dogs I am currently unemployed for the past 20 years I’ve been raising my kids. Looking for a job! I have a very flexible schedule. I love spending my time with dogs. Make sure they are happy and loved. Feed and make sure they get enough food, water and affection. Most of all exercise love and safety

Sitter Profile Image: Perri E.
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Perri E.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 95 reviews
27 repeat clients
10 years of experience
Ballwin, MO, 63021

About: I'm a caring person who will pay attention to your pet's needs and spend time with them. I had a dog for 6 years before she passed away. She was a German Shepard chow who loved going on walks in the park. I love being outdoors, whether for business or personal health, Disney, and cooking. I follow instructions to a T and will protect your pet at all costs! When house sitting, I always treat the house better than I would treat my home. I clean up after myself, and will provide my own food as I care for your home and pet. I am willing to stay at your house 24/7, while you're away, if you desire it. You will not be disappointed with me as your sitter! My schedule is rather open and quite flexible. I can provide care to cover all your needs; be it a short walk or days to weeks for your vacation! I double-check all doors in my client's homes throughout my stay. I've had no pet break-outs or escapes yet and I will keep it that way. I make sure to keep all human foods out of reach to pets and clean up all my trash. No one is eating trash on my watch

Sitter Profile Image: Elizabeth H.
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Elizabeth H.
from
$16
per walk
4.9 out of 5 stars
• 59 reviews
15 repeat clients
30 years of experience
Ballwin, MO, 63011

“Elizabeth is wonderful! She really helped me out with a quick work trip and my fur babies are always so happy when I get home. I will certainly be rebooking for my next trip!”

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Christy R.
Sitter Profile Image: Amber M.
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Amber M.
from
$32
per walk
6 years of experience
Ballwin, MO, 63021

About: Ive been an emergency vet tech and helping hand for 6+ years. Ive had animals my entire life & adore them so much I made a living off keeping them safe & healthy. Your loved ones will be loved in my home & heart. I work long hours but that means I have more days off to help you out. 3 days out if the week i have off & can accommodate your oets here in my home or stop by your house for potty breaks/walks. My yard is fenced in, my animals are very friendly, my teenage son loves animals & hopes to follow in mom's footsteps in vet med.

Sitter Profile Image: Perrin W.
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Perrin W.
from
$30
per walk
5.0 out of 5 stars
• 7 reviews
2 repeat clients
40 years of experience
Ballwin, MO, 63021

About: I had pets as child and always have had dogs and cats as an adult, and felt it important for children to be around pets I am retired, arise early and love to be outdoors. I especially like walking, might as well have a dog with me when I walk. I will follow all guidelines given to me by the pet owner, will have contact with the owner before and while caring for their pet/pets.

Sitter Profile Image: Michael & Beth H.
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Michael & Beth H.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
• 271 reviews
64 repeat clients
35 years of experience
SAINT LOUIS, MO, 63122

“Mike was great! Helped me out of a bind at the last minute. He took great care of my dog, and followed my instructions. I totally recommend Mike!”

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Anne H.
Sitter Profile Image: Claire R.
Verified Enhanced Background Check
Claire R.
from
$16
per walk
15 years of experience
Chesterfield, MO, 63017

About: My pet care experience includes tailoring physical activity to a pets age/ability level, recognizing a pets cues on their overall comfort level, and administering various forms of medication. My family would regularly take in senior dogs when I was growing up so I am used to assessing their needs. I am available mornings, evenings and around lunchtime. My work and school schedules allow for flexibility and I am happy to work with you to find times that are best suited for you and your pet. My apartment building unfortunately does not allow any type of animal so I am not able to offer boarding. I would like to apologize for the inconvenience.

Sitter Profile Image: Kate B.
Verified Enhanced Background Check
Kate B.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
• 35 reviews
13 repeat clients
40 years of experience
Fenton, MO, 63026

“Kate did a fabulous job walking/watching Lilly!! She was caring and attentive!!! will be using her again!!!”

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Katie S.
Sitter Profile Image: Joseph K.
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Joseph K.
from
$25
per walk
2 repeat clients
10 years of experience
Ellisville, MO, 63011

About: I grew up with mastiffs, trained dogs as a volunteer at a local shelter, and have loved dogs for as long as I can remember. I’ve been walking dogs and caring for my own for years I’m building my own business, so my schedule is as open as I need it to be. I walk my own dog on a schedule twice a day, but have no other rigid commitments. Safety first. Leashes are always secured and checked before doors are open. If going into a fenced yard, gates are checked and dogs are supervised at all times.

Sitter Profile Image: Madison & Eric T.
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Madison & Eric T.
from
$20
per walk
5.0 out of 5 stars
• 66 reviews
18 repeat clients
8 years of experience
St. Louis mo, MO, 63146

“Madison is super responsive and sends lots of pictures and videos which brightens my day! My puppy is so happy to spend time with her and we will use her frequently going forward.”

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Amber T.
Sitter Profile Image: Nora T.
Verified Enhanced Background Check
Nora T.
from
$20
per walk
5.0 out of 5 stars
• 9 reviews
3 repeat clients
10 years of experience
Kirkwood, MO, 63122

About: I have taken care of all kinds of animals since I was 14; Dogs, cats, horses, you name it! In recent years, I have pet sat (Dogs, cats, fish, guinea pigs, and even a bearded dragon!) for 5 different families with regularity, relying on me to walk, feed, and bathe their pets. I took some time off to focus on my full-time job but now I am back to take care of your fur babies! I have experience with breeds of all shapes and sizes, and love to learn about each pets needs, quirks, and their favorite spot to be pet! I work as an RN full time 12 hour shifts, typically overnights! If you need a quick walk or drop in visit in the early mornings, mid day, and early evening, I'm your gal! If you need a quick drop in while you are at work or running errands, I'm your gal as well! I do not mind late night drop ins or walks as well, I am pretty flexible for walks and drop ins throughout the day if I’m not working at the hospital or studying at school. I love to walk parks and hike through trails, and your dog can come along for the ride anytime!! I am always very respectful of boundaries and client's homes. I will care for your pets just as you would, providing them with as much attention and love they desire! I am always respectful of your pets boundaries as well, and will never put them in a stressful situation. I currently live in an apartment that only allows cats, and I have one kitty cat named Booker. I am a nursing student and I study quite a bit. If your pet needs a person who can chill and keep them company, I can 100% provide that! If your pet needs someone to play and run around with, I can 100% provide that as well! If your pet has medical administration needs, I have experience with this as well. One family that I pet sat regularly for had a kitty who needed insulin via injection two times a day, another had a pupper that needed two pills at morning and evening feedings. I am always punctual with medicine times and I follow instructions very closely.

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The median cost per walk for dog walking in Winchester is $20

Dog parents share their Rover experiences - Winchester

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5.0 out of 5 stars

Jennifer was awesome! Reliable, friendly, and very caring for our Riley. We would recommend her highly!

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Lenny S.
Dog Walking
5.0 out of 5 stars

Cynthia is amazing. Our dogs loved her. She stayed in contact and sent pics after every walk. I had nothing to worry about and will definitely hire again.

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Krista T.
Dog Walking
5.0 out of 5 stars

Lacy and Piper are always so excited to see Greg and Jane for walks. They are always on time and walk the dogs on the route I requested and give them lots of pets. I will definitely request Greg and Jane when I need dog sitting or the dogs walked.

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Mary Ann L.
Dog Walking
5.0 out of 5 stars

Jennifer was able to help me out on a last minute request to walk my dogs as I had to leave town. She walked both my dogs on a short notice and was great with them. Will book again!

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Nick D.
Dog Walking
5.0 out of 5 stars

Great skill in handling a large strong dog. Best thing is my dog looks forward to his walk with Sam.

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Jackie V.
Dog Walking
5.0 out of 5 stars

Very capable and very sweet. Riley loved her. We will definitely be booking with Lindsay many times. Rover has a winner with Lindsay.

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F. K.
Dog Walking
5.0 out of 5 stars

Lawton was awesome, I’m so impressed with how she cared for my pup on short notice! Will definitely be booking her again!

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Sarah S.
Dog Walking
5.0 out of 5 stars

Thomas is very responsive, thorough and provides feedback about whatever he is doing for Owen each visit. I appreciate all of his help while I am away. Thank you Thomas!

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Jane S.
Dog Walking
5.0 out of 5 stars

Charles was AWESOME! I’ll recommend him everytime.. booked walking for my dog and it was my first time ever hiring a dog walker or using Rovr. I love the updates and communication and photos of my pet. I felt at ease and comfortable. I knew my dog was in good hands. Great service!

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Mrs Nichole P.
Dog Walking
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How to book dog walking

  1. 1. Search

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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 $19 per walk as of November 2026. Most bookings cost between $13 and $28 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 November 2026, there are 2,468 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 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 a map of the walking route, 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 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:

  • 89% of walkers can help with special care needs
  • 94% 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 Meet & Greet.

walkers on Rover set their own cancellation policy, 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.

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