Dog Walking Winchester

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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: Marilyn O.
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Marilyn O.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
52 reviews
17 repeat clients
30 years of experience
Oskaloosa, KS, 66066

About: **About me** I have always wanted to move to the country and care for animals all my life. My husband (Patrick) and I currently have three rescue dogs and 5 outdoor rescue cats. We also have two horses Valentine and Peanut that love to walk the trails with us. My passion is caring for animals and I have had years of experience raising all breeds and types of pets! We live in a small home built on 31 beautiful acres. We have a fully fenced large back yard and several wooded trails, a beautiful pond in the front yard and lots of room to play! Your pets will love coming here and it will truly be like they are on vacation. I have 4 grand pups that come to the farm regularly and they get very excited to visit. **About my home/services** I will provide a loving and fun environment for all pets that come here to stay! They will be safe and will love every minute of their stay! **About my neighborhood** We live on 31 acres with only 1 neighbor close. We have a fully fenced back yard and a pond to fetching toys if your pet loves to swim. We have wooded trails that we often take walks on and we will have lots of exercise or just hanging out in the back yard.

Sitter Profile Image: Terese S.
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Terese S.
from
$25
per walk
10 years of experience
Valley Falls, KS, 66088

About: I’ve worked professionally in animal welfare for two years. I’m a certified pet sitter for both dogs and cats while also being pet first aid and CPR certified as well. I’m also fear free certified. I’ve owned my own dogs and cats for the last 10 years! I currently work part time in animal welfare. I’m able to come to your home Tuesday, Thursday or Friday anytime in the afternoon after 12:30. I can come to your home and walk your dog for fresh air and exercise or I can do a pet visit where I check on your dog/cat! In the comfort of your home I can let a dog out to their yard, feed/water cats or dogs, play time etc

Sitter Profile Image: Jenna C.
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Jenna C.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
21 reviews
5 repeat clients
8 years of experience
Fort Leavenworth, KS, 66027

Jenna was so sweet and caring to my dog Ollie. She saw that he had relentless energy and would walk over the time I paid for.

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Haley V.
Sitter Profile Image: Alyssa M.
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Alyssa M.
Star Sitter
from
$40
per walk
4.9 out of 5 stars
56 reviews
26 repeat clients
15 years of experience
Leavenworth, KS, 66048

It was truly a pleasure to have Alyssa walk our girls on a regular basis. She's responsive, flexible, but above all, reliable. We thank you for being an outstanding Rover!

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Nate S.
Sitter Profile Image: Sarah B.
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Sarah B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
12 reviews
4 repeat clients
10 years of experience
Lawrence, KS, 66044

About: Hi, I’m Sarah! I’m 18 years old and have loved animals for as long as I can remember. I grew up with both dogs and cats and currently have four dogs of my own, so caring for pets has always been a huge part of my life. I currently work at a dog daycare in Lawrence, where I care for dogs of all sizes, breeds, ages, and personalities. My job includes supervising playgroups, feeding, giving medications, monitoring behavior, and making sure every dog is safe and happy. Working with so many different dogs has taught me how important it is to treat every pet as an individual. I’m also very comfortable caring for cats. Whether your cat is outgoing and social or prefers their own space. I recently graduated high school and will be attending JCCC this fall to start my pre veterinary studies. My goal is to become a veterinarian! My boyfriend, Cameron, is 20 years old and helps me with pet sitting. He absolutely loves animals and has a lot of experience with them. He helped train our German Shepherd from the time he was a puppy and did an amazing job with him. He also grew up with several cats, so he’s very comfortable around both dogs and cats. I just like to be upfront that he may accompany me on visits or overnight stays. We’re both huge animal lovers and enjoy spending time with pets! I work Tuesday through Friday from 7:00 AM to 6:00 PM, but I’m available before work, during my breaks, and after work. I also have full availability on weekends and Mondays. Pet care fits naturally into my schedule, and I do my best to be flexible to meet your pet’s needs. When I’m caring for your pet in their own home, my goal is to keep their routine as normal and stress-free as possible. Whether that’s feeding, walks, playtime, medications, or plenty of cuddles, I’ll make sure they get the attention and care they deserve. I know how important it is to trust someone with your pets, and I treat every animal as if they were my own. I’d love the chance to meet you and your pets! Feel free to reach out with any questions or to set up a meet and greet.

Sitter Profile Image: Emma L.
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Emma L.
from
$15
per walk
5.0 out of 5 stars
5 reviews
2 years of experience
Lawrence, KS, 66049

About: I have been working for a dog boarding and daycare facility for about a year and a half now! I have learned lots about dog behavior and how to interact with lots of different personalities- and I am still learning every day! I have experience in administering medications and would love to meet your pup! I currently work full-time caring for pets at a daycare facility, typically working either 6-1 or 1-7 Tuesday through Saturday. Fully available on Sunday and Monday! I have my own pup who is fixed and very friendly! I can bring him along if you want your dog to have any socialization or burn extra energy, but I am also more than happy to focus on your pet!

Sitter Profile Image: Anna B.
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Anna B.
from
$27
per walk
3 years of experience
tonganoxie, KS, 66086

About: I’ve taken care of dogs and cats for a while now! I have had the responsibility to feed, walk, bathe, play, and love for the animals of friends, family, and coaches! Currently for the summer, I only work in the evenings! I will have plenty of time during the day to take care and love on your animals! I have many toys for my cats they keep them stimulated, I also have travel gear to take them in car rides with me! My dogs have a big fenced in backyard, they love going for walks and hikes, and love to play in kiddie pools!

Sitter Profile Image: Brianna G.
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Brianna G.
from
$18
per walk
5.0 out of 5 stars
4 reviews
7 years of experience
Tecumseh, KS, 66542

About: Hi! I’m a reliable, experienced pet care provider with a flexible schedule and hands-on experience with dogs of all personalities, including those who are shy or slow to warm up. I’ve worked closely with behavioral specialists, so I’m comfortable reading dog body language, following care instructions, and managing different routines or environments. Whether your pup needs a friendly face for walks, check-ins, or companionship while you’re away, I take pride in providing thoughtful, stress-free care. I’m organized, attentive to details, and always prioritize safety and comfort—wherever your dog is happiest. Remote job, flexible schedule. Monday-Friday only, weekends are generally open outside of planned events and activities. I finish work at 5pm daily, but it's a very adaptable work routine. When it comes to care routines, I'm consistent and structured. I typically do potty breaks at minimum every two hours and provide walks one to two times daily, adjusting the length based on each dog's energy level and preferences. Fresh water and food are always available unless you specify otherwise. I keep my own dog separate from visiting dogs unless they've had time to become familiar with each other, which helps everyone feel more secure.

Sitter Profile Image: Marianna M.
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Marianna M.
from
$15
per walk
4.9 out of 5 stars
17 reviews
7 repeat clients
6 years of experience
Parkville, MO, 64152

About: I have been in the animal field since I was 16, completing a veterinary assistant program during high school. During Covid, I helped my aunt foster 3 rescue beagles as well as caring for her other two dogs. Since then, I have worked at multiple doggy daycare and boarding facilities and have pets of my own! I work 6am to 6pm every Tuesday-Friday so ideally, I’d need flexibility on drop-in visits for those days, but I have open availability on the weekends + Monday I am currently only providing drop-in visits which means your pet/s will stay in the comfort and safety of their own home. I always do meet n greets where the pet will be staying.

Sitter Profile Image: Sean H.
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Sean H.
from
$50
per walk
5.0 out of 5 stars
28 reviews
8 repeat clients
20 years of experience
Lawrence, KS, 66044

About: "If you can look at a dog and not feel vicarious excitement and affection, you must be a cat." ~Terri Guillemets Love dogs (and animals in general, but dogs especially.) I have been around them my whole life and wouldn't want it any other way. I come from a large, mostly rural dwelling family, my grandma had 11 kids 2/3 of which have at least 1 or more dog(s) including my mom. I've always had my own and/or lived with roommates/friends/family, that have/had dog(s) in every house I've lived from day 1 to the present. Although I can't say I've taken care of every breed out there (doubt that many people can) I have definitely seen my fair share of mutts and purebreds alike; from Corgis to Chihuahuas, Danes to Dobermans, Lhasa Apsos to Shar Peis, and even a couple of wolves (3/4 mixes) as well as a few rodents, cats, reptiles, arachnid and birds. Big or small I love "em all, but if you forced me to pick a favorite I'd have to go with the affectionate yet intimidating Perro de Presa Canario. In short, if either by choice or necessity you find yourself in need of a caretaker for your 4-legged (or more) companion(s), know that I would be elated for the opportunity and you can be assured that their health and well-being will invariably be at the forefront of my mind in all that I do while they're in my care. Thank you for taking the time to read this and I look forward to hearing from you soon. "Lots of people talk to animals.... Not very many listen, though.... That's the problem." ~Benjamin Hoff, The Tao of Pooh

Sitter Profile Image: Faye D.
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Faye D.
from
$15
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Parkville, MO, 64152

Faye is the best. We got to leave our 2 dogs for 8 days for a vacation. She sends photos and truly cares for our pooches..

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Jenny L.
Sitter Profile Image: Sydney W.
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Sydney W.
from
$25
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
9 years of experience
Gardner, KS, 66030

About: My family has had dogs, cats and fish my whole life. I often watch them when my parents are out of town and I have dog and cat sat for family & friends for years. I have helped a friends family with their cattle and pigs, but am not as experienced with livestock outside chickens. I’m currently available 7 days/wk I work as a server in my pleasant so whoever I’m staying with ideally should be able to go 6-8hrs between potty breaks! If I have 2 weeks or more advanced notice I can make arrangements to be able to check in more frequently. o o o o o o o o o o I love interacting with the pets and getting to see them get more comfortable with me. I am very comunicative and willing to ask questions.

Sitter Profile Image: Linda G.
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Linda G.
from
$35
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Topeka, KS, 66606

Linda has watched my dog a few times now, and has been very patient with him. He can be a little timid, but has really started to warm up to her!

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Kelby C.
Sitter Profile Image: Brooklyn R.
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Brooklyn R.
from
$25
per walk
5.0 out of 5 stars
3 reviews
4 years of experience
Westwood, KS, 66205

About: I have three dogs, two wonderful twin golden retrievers that are 5 years old. They are my whole world and so are my sister and brother’s dogs/cats! My sister has been doing rover in KC for over 7 years so it’s been a great way to experience rover and the necessities for all kinds of pets. Additionally, I’ve been a volunteer at Unchained Melodies puppy nursery and KC Pet Project for the last few years <3 I’m currently a post-graduate student preparing for medical school here in a year so I have a lot of time for longer term pups. I’m preparing for work part-time as well in the fall but I have a very open and flexible schedule. I have helped dog sit for years now and of course I’ve taken care of my own dogs since they were just babies. Unfortunately, I’m unable, for the most part, to have animals stay at my house however, I’m open if necessary. I walk and feed my own dogs daily and they take a lot of space so I want them to feel comfortable in their own environment.

Sitter Profile Image: Danyelle S.
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Danyelle S.
from
$40
per walk
17 years of experience
St Joseph, MO, 64501

About: I’m an active adventurous person ready to play with the dogs or take them on walks. I have helped family, friends and neighbors watch their dogs, whether it be just a check in or a week at a time! I work as a phlebotomist in my other times, help family and create crafts for my page! Seeing as I have a cat of my own, I make sure to put her into my daily schedule and make time for her to play with her and her as well as make sure her litter stays clean and her food and water bowl stay full! My cat is an indoor cat. Although she is aloof, she still loves to come cuddle and I always make sure that her food and water bowls are full, her litter is clean and her medicine is taken

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

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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    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

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Sitters in Winchester average 3
repeat dog walking clients

FAQs for Dog Walking - Winchester

Frequently asked questions about Rover

As of July 2026, there are 519 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:

  • 90% of walkers can help with special care needs
  • 100% 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.

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