Dog Walking Winchester

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

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Over 7
pet parents in Winchester have booked dog walking

Winchester, Find top rated dog walking

Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Cyrissa B.
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Cyrissa B.
$20
total per walk
5.0 out of 5 stars
284 reviews
31 repeat clients
10 years of experience
Hemet, CA, 92545

Layla loves Cyrissa, she has been with us for almost 3 years. My dog Layla (16) was struggling with health issues and Cyrissa took her time with her and listen to Layla’s needs. I can vouch for Cyrissa 100 percent. Always very attractive and loyal Loyal to my girls. I will continue using CyrissA for my other dog Moo Moo is is late in age (14) and struggling with anxiety, I know I am at ease when Cyrissa is in charge of her because, she listens to her needs. Thank you for being so supportive and caring for us. I highly recommend and encourage everyone who needs help with walking or sitting. Best of luck 🤞

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Angel L.
Sitter Profile Image: Dawn B.
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Dawn B.
$28
total per walk
5.0 out of 5 stars
70 reviews
26 repeat clients
15 years of experience
Menifee, CA, 92585

Dawn is great with my dogs (one being a puppy!) and is very responsive and responsible. I feel like my dogs are in good hands when they are on walks with her!!

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Heather H.
Sitter Profile Image: Lili J.
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Lili J.
$28
total per walk
4 years of experience
Menifee, CA, 92584

About: What sets me apart is the trust I've built with my clients. Many are repeat clients who feel comfortable leaving their pets in my care, even for vacations lasting over a month long. I'm reliable, highly responsive, and believe communication is key. I'll keep you updated with photos and messages while following your pet's routine to help them feel safe, comfortable, and loved. From tiny cats to large dogs, I treat every animal as if they were my own and every home with the utmost respect, so you can enjoy your time away with complete peace of mind. I have a flexible schedule, which allows me to provide pets with plenty of attention, exercise, and companionship throughout the day rather than just quick check-ins. Whether it's walks, playtime, feeding, or simply keeping them company, I enjoy making sure each pet feels comfortable and cared for. As a pet owner myself, I understand the importance of consistency and sticking to your pet's normal routine. I always strive to make them feel safe, happy, and loved while you're away. I believe pets are happiest when they can stick to their normal routine. During overnight stays, I provide full care including feeding, fresh water, walks, potty breaks, playtime, cuddles, and any medications or special instructions if needed.

Sitter Profile Image: Jennifer M.
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Jennifer M.
$34
total per walk
5.0 out of 5 stars
160 reviews
77 repeat clients
36 years of experience
Winchester, CA, 92596

About: Hi I’m jen . I was a personal trainer , but I found my true passion in working with animals especially dogs !! I have a big yard to play in, and two very friendly little dogs . I’ll treat your dog like my own , because I know how difficult it is to leave your fur babies and feel at ease. I send tons of videos and pictures to make you feel they’re still with you while away ! Just give me all your concerns and I’ll do my best to make you worry less on your trip ! I’ve loved dogs since I was a kid and grew up on a ranch with many along with many other animals so I know how to take care of them . I’ve also recently been taking online vet tech courses just to have the extra knowledge in caring for your fur babies ! Seniors I’ll take extra caution and care because I know they’re fragile and need more loving . I do often sit 5+ at Once as long as they all get along and I feel social interaction is Great for dogs as well ! I hope to meet your furry kids soon ! Love ❤️ Jen I’m full time pet sitter so I’ll have all my time to focus on your pets needs .just text me anytime with any questions or concerns. I keep my place puppy proof and supervise 24:7 and cater to any needs your pups should have . Feel free to text or call anytime! I wake around 6-7 am and in bed around 10pm so I’ll try to work with you on your schedule because I do this full time. I have a fenced yard and extra crates if you prefer yours crated to eat or at night . Otherwise they’re welcome in my room .

Sitter Profile Image: Ashleigh D.
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Ashleigh D.
$28
total per walk
5.0 out of 5 stars
3 reviews
1 repeat client
25 years of experience
Winchester, CA, 92596

About: I have experience with all shapes, sizes and temperaments of animals. I currently own two large dogs. I have experience walking reactive dogs and fearful dogs. I have also cared for elderly pets and trained quite a few puppies! Knowing how particular I am with my own pets, I take your care instructions extremely seriously and will ensure you pet has nothing but the best while you are away. I work from home and am my own boss so my time is very flexible to give your pet all that they need! I can do check-ins or walks all times of the day. I am happy to follow your lead on whatever you like your dog to do every day! Backyard playing or walks around the neighborhood. Whatever your dog likes best, I can do!

Sitter Profile Image: Estefany D.
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Estefany D.
$23
total per walk
5.0 out of 5 stars
27 reviews
8 repeat clients
7 years of experience
Menifee, CA, 92584

Estefany was so kind and patient with my elderly and sometimes stubborn pup!

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Veronica P.
Sitter Profile Image: Kimberly C.
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Kimberly C.
$28
total per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
26 years of experience
Menifee, CA, 92584

About: I started caring professionally for animals when I was just 16 years old. In the veterinary facilities over the years, I worked my way up from kennel attendant, to customer service representative, to customer service supervisor, to customer service manager, to reproduction veterinary assistant. Over these years I have cared for dogs and cats of all ages. During my time as a reproduction veterinary assistant, I found a passion for breeding/deliveries/neonatal puppy care etc. I took this passion and started caring for other people’s pregnant momma dogs within my home. I delivered the puppies, and raised them for infinite weeks until said breeders found their forever families. I raised, cared for, and trained over 150 puppies within my home during the last 4 years. I established long lasting relationships with not only the momma dogs families, but also the families of many of the puppies I was blessed to raise here. Many of which now come to me to watch and care for their dogs/puppies while on vacation, busy day at work, or maybe need a bath/blowdry/brushout/nail trim etc. when needed. I wanted to open up my home and extend my love and animal care for anyone else who may need my service. I am home all day most days. Now that my kids are grown and come and go on their own, I have ability to care for others pets and fully accommodate any needs they may have. When pets are in my home, they can roam freely within designated areas, sleep in beds with us like they are family, or be crated off and on if preferred by their families. We have a fenced yard for outside playtime and a designated turf area for dogs to do their business.

Sitter Profile Image: Keiona D.
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Keiona D.
$23
total per walk
5.0 out of 5 stars
7 reviews
3 repeat clients
13 years of experience
Winchester, CA, 92596

Highly recommend! Took care of our 3 dogs while we were away and very tentative to instructions. Communicated perfectly if we needed adjustments and our dogs were so excited to walk with her when she arrived at our house. Will definitely use her again in the future! Thank you Keiona!

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Alyssa B.
Sitter Profile Image: Jenny D.
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Jenny D.
$35
total per walk
5.0 out of 5 stars
178 reviews
41 repeat clients
40 years of experience
Menifee, CA, 92584

Jenny is so great with Luna and really pays attention to her needs, and or if she just needs to rest. I will continue to request Jenny for our future needs.

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Melissa M.
Sitter Profile Image: suamya s.
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suamya s.
$28
total per walk
3 years of experience
Menifee, CA, 92584

About: I have over 3 years of experience caring for dogs and have worked as a pet sitter for three different families. During that time, I cared for dogs with different personalities, sizes, and energy levels. My responsibilities included feeding, providing companionship, administering basic care, and following each family’s specific routines and instructions. I am a college student with a flexible schedule, which allows me to dedicate quality time to the pets I care for. I truly enjoy being around dogs and love spending time walking, playing, and giving them the attention they deserve. I always make sure to follow each pet’s routine. Your pet’s safety and comfort are my top priorities. I carefully follow all instructions regarding feeding, medications, walks, and routines. When caring for pets in a client’s home, I respect both your home and your pet’s routine to help them feel comfortable and relaxed. I keep the environment clean, provide fresh water, monitor their well-being, and give them attention. I believe clear communication is essential, so I provide regular updates and photos throughout each visit.

Sitter Profile Image: Carolina E.
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Carolina E.
$28
total per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
8 years of experience
Menifee, CA, 92596

I love how I got constant updates and frequent pictures of Gunner. It definitely provided me peace of mind, knowing he was well taken care of during the visit. Highly recommended!

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Jessica L.
Sitter Profile Image: Lexie R.
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Lexie R.
$22
total per walk
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Menifee, CA, 92584

About: Ive had pets since I was a child. Frogs, fish, turtles, dogs/puppies, bunnies, and a parrot. I would say I am well rounded in pet care. I am able to board small dogs, I also can watch your furbaby in home if you like. If you need someone to drop in and take care of your pet while out I am also willing to do that. I know how to administer oral medications if that is of need. I currently only have two rabbits and a fish tank so your pet wouldnt interfere with any of mine. I board only one pet at a time so that I can give full attention to that furbaby. Making your pet comfortable and happy is what I strive for when you see your furbaby again. I am currently working from home so I have more than enough time to take care of your animal. I will be available to feed , and do any extra activities they your animal may need. I have a fenced in yard, and can crate if needed. Please bring your own crate I do not have extras at my home yet.

Sitter Profile Image: Benny C.
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Benny C.
$34
total per walk
5.0 out of 5 stars
39 reviews
21 repeat clients
10 years of experience
Menifee, CA, 92585

About: 1. First of all I have my own dog (full time) and two other dogs (part time) in my care and my passion and excitement is around with dogs. 2. I communicate with dogs as my own children and care for them unconditionally. Making sure I understand their needs like personal relief every so many hours, food at required time, exercise and outdoor activities when weather permits. 3. I am retired now so I have all the time to do this from 6 AM to 6PM everyday. 4. My home is catered for Dogs, well fenced and lots of yard to play around, live in a community with a lot of Dog Lovers and green belts to Walk. 5. My wife who is also a Dog Lover will be with me attending to the dogs.

Sitter Profile Image: Juliet D.
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Juliet D.
$26
total per walk
6 years of experience
Romoland, CA, 92585

About: Im home 24/7 so you need a sitter dog, walker im there 😭 all I do currently is take care of 4 dogs. Always make sure they get their walk so they stay fit, I never over feed, make sure they get their outside play time and nap time I am on it. I currently have plenty of spare time so im very free everyday to go on walks, play take care of a dog whenever needed. Currently do that right now with my own little weiner army all I do all week is take care of dogs. I have 4 small weenies who love to dig and play in the big back yard and i take them on walks every day or every other day depending on their energy. They do mostly love to sleep throughout the whole day and dig.

Sitter Profile Image: Ashley L.
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Ashley L.
$22
total per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
1 year of experience
Menifee, CA, 92586

About: I’ve assisted with dog sitting alongside my mom and grandma, helping with playtime, and companionship. I’m patient, attentive, and following routines to ensure dogs feel safe and cared for. Pet care fits easily into my daily routine. I have flexible availability as I am unemployed and already care for my own two cats and two bearded dragons daily. I provide attentive care in peoples homes, following routines closely. As an owner of two cats and two bearded dragons, I’m experienced with safety, cleanliness, and gentle handling.

Sitter Profile Image: Raelynn L.
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Raelynn L.
$26
total per walk
5.0 out of 5 stars
8 reviews
2 repeat clients
4 years of experience
Menifee, CA, 92585

About: I offer personalized care with genuine love for pets, ensuring they feel at home and receive individual attention tailored to their needs. Since I don’t have any pets of my own, all my affection and focus will be dedicated to your furry friend, providing endless love, cuddles, and scratches to make them feel truly cherished. I have a flexible work schedule that allows me to care for your furry friend throughout the day. I make sure they’re fed, watered, and get plenty of outdoor time. I have a yard that gives pets more space to play, relax, and get their energy out, and I also love taking them on walks for extra exercise and stimulation. In both my home and your pet’s home, I prioritize safety, trust, and a nurturing environment. I ensure safety by securing all areas to prevent accidents and regularly checking for potential hazards. Trust is central to my care approach, so I maintain open communication with you, providing regular updates on your pet’s well-being. I create a comfortable and clean environment tailored to your pet’s needs, with consistent routines and plenty of affection to make them feel secure and loved.

Sitter Profile Image: Tara C.
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Tara C.
$28
total per walk
5.0 out of 5 stars
23 reviews
5 repeat clients
10 years of experience
Menifee, CA, 92584

Tara is wonderful with Briggs during the day while I'm at work. She always supplies pictures and a little blurb about their walk, which I love reading. She's also good about bringing things to my attention, whether it's a comment (about Briggs) made by one of my neighbors or if he seems to have trouble defecating. One of my neighbors even made a point to let me know how great she is with Briggs. Definitely recommend.

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Amy K.
Sitter Profile Image: Vicki C.
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Vicki C.
$23
total per walk
5.0 out of 5 stars
22 reviews
8 repeat clients
40 years of experience
Summerlin North, Menifee, CA, 92584

About: My name is Vicki. I am a 59 year old wife, mother, grandmother and animal lover. I have worked with Veterinarians over the years and have fantastic references. One of my best friends is a veterinarian. We have 2 dogs of our own (my hubby and I.) We spoil them rotten! I have an animal science degree and a HUGE compassionate heart. Animals are truly my heaven on earth. I am a responsible, loving and trustworthy pet companion. Why I love dog sitting: Since I was a child! I have grown up with pets and never been without an animal in my life. About my yard: Dog area, dog door to freely come in and out. I dedicate 100% of my time to your pet with love and compassion and exercise. You will have freedom to know your pet is well taken care of. My home is pet friendly and has a fenced area with a dog door. It is easy access to go in and out to go potty.

Sitter Profile Image: Paulena G.
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Paulena G.
$22
total per walk
5.0 out of 5 stars
43 reviews
10 repeat clients
15 years of experience
Menifee, CA, 92586

This is my first experience using Rover and I feel like I lucked out immediately finding Paulena. My dog (and mom) loved her. Paulena is communicative and kind. I’ll definitely book with her again. Thank you!

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Xylene C.
Sitter Profile Image: Owen L.
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Owen L.
$35
total per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
22 years of experience
Menifee, CA, 92584

About: Over 22 years hands on experience with all size dogs/cats. Specialized in animal behavior and non-anesthetic dentistry. I care for pets like their my own I recently left my job of 10 years in Veterinary Dentistry for a change of pace. My intention is to give pet sitting/care full attention. Everything I will do/provide for my clients will be solely based on their unique circumstances/behaviors etc. Basically tell me what you need and will accommodate.

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The median cost per walk for dog walking in Winchester is $25

Dog parents share their Rover experiences - Winchester

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5.0 out of 5 stars

Wow! Paco loved James and he usually takes a while to warm up to people! James was easy to work with and has the best attitude! We will be contacting James again for more dog walks! Thanks again James!

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Liz F.
Dog Walking
5.0 out of 5 stars

James did great with my little pup. Dickie is usually very shy with strangers but was very comfortable with James. Dickie had a lot of fun. I will definitely be contacting James again.

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Robert S.
Dog Walking
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Meet local walkers who will treat your dogs like family

  1. 1. Search

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Sitters in Winchester average 3
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 $23.31 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 3,584 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
  • 96% 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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