Dog Walking Winchester

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

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Over 6
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: Ricki H.
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Ricki H.
$23
total per walk
5.0 out of 5 stars
• 5 reviews
4 years of experience
Winchester, CA, 92596

“Ricki was a fantastic dog walker! She was very attentive and kept us well updated. We mentioned that something was important to us and she made sure to keep us updated about that in particular. She even reached out to let us know our heater had been left on (by a family member stopping by) and the house was hot! Some people might be too nervous to say something and would assume that we left it on on purpose. Reaching out was the best thing to do and we really appreciated it.”

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Mariah L.
Sitter Profile Image: Cyrissa B.
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Cyrissa B.
$28
total per walk
5.0 out of 5 stars
• 321 reviews
37 repeat clients
10 years of experience
Hemet, CA, 92545

“Mila loves Cyrissa and does well with her walkies (it’s surprising since she’s very wild) and we are members of Rover because of her. Thank you!”

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felipe g.
Sitter Profile Image: Ramey K.
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Ramey K.
$23
total per walk
5.0 out of 5 stars
• 129 reviews
47 repeat clients
15 years of experience
Menifee, CA, 92584

“Ramey did a wonderful job of taking care of 3 dogs! She patiently dealt with each one of their personalities and needs. I would highly recommend Ramey for any pet care services.”

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David M.
Sitter Profile Image: Dawn B.
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Dawn B.
$28
total per walk
5.0 out of 5 stars
• 75 reviews
29 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: Estefany D.
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Estefany D.
$27
total per walk
5.0 out of 5 stars
• 31 reviews
10 repeat clients
9 years of experience
Menifee, CA, 92584

“Estefany is great! She is great at communication and care for your dog like her own 😊”

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John D.
Sitter Profile Image: Ashleigh D.
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Ashleigh D.
$22
total per walk
5.0 out of 5 stars
• 6 reviews
2 repeat clients
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: 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: Lili J.
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Lili J.
$28
total per walk
5.0 out of 5 stars
• 8 reviews
1 repeat client
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: Creedawnn G.
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Creedawnn G.
$35
total per walk
5.0 out of 5 stars
• 5 reviews
2 repeat clients
10 years of experience
Winchester, CA, 92596

About: Of all animals I have the most experience with dogs. I love dogs all shapes and sizes We've always had a dog at home and I have lots of experience, caring for playing with and walking dogs, including bath time. I'm a recent graduate of heritage high school. I took agriculture at school and worked with the animals on our school farm I'm looking to do rover as often as possible. I don't have any other obligations at this time. So I can dedicate myself to your pets. I am very careful about fences and doors. I'm mindful of owner instructions regarding where their pets can be. And where they are not allowed. I am mindful of them while they are eaten. And while they are playing, to make sure that they remain safe. I checked the pavement before I take a dog out on walks to make sure it's not too hot and always make sure to wash their bowls so that I can help prevent bacteria

Sitter Profile Image: Briana Z.
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Briana Z.
$22
total per walk
5.0 out of 5 stars
• 2 reviews
8 years of experience
Hemet, CA, 92545

About: ⭐️ Former D1 athlete, so discipline and follow-through come naturally ⭐️ Specialize in gentle, steady-paced fitness routines for senior or overweight dogs ⭐️ Meticulous drop-in care for cats and small caged pets ⭐️ Welcome healthy adult dogs, puppies, and pets of all shapes and sizes! ⏰ On time, every time, no exceptions ⏰ No rushing, every visit gets my full attention ⏰ Pets stay on their familiar, vet-approved routines while you’re away 🏡Treat your home with executive-level respect 🏡 Keep your space immaculate and your privacy protected 🏡 A calm, quiet, focused presence from start to finish

Sitter Profile Image: Kimberly C.
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Kimberly C.
$32
total per walk
5.0 out of 5 stars
• 28 reviews
5 repeat clients
26 years of experience
Menifee, CA, 92584

“Kimberly is the BEST!! Our two dogs absolutely love her! She is very communicative, prompt, and so sweet with the dogs. We are very grateful that we have found her!”

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

About: My sister and I 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: Jayda b.
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Jayda b.
$23
total per walk
10 years of experience
Menifee, CA, 92584

About: "I bond with pets instantly, offering playful training for pups and gentle care the for seniors. My 20 years bring youthful energy and responsible attention." Pet care is a big part of my day. I schedule in walks, playtime, feeding, and grooming, making sure each pet gets the attention they need! Because I have dogs of y own and been a dog owner since I was about 10 years old! In my home and yours, I prioritize safety with secure spaces and constant supervision. Trust is built through consistent, loving care, creating a stress-free environment.

Sitter Profile Image: Juliet D.
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Juliet D.
$26
total per walk
1 repeat client
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: Kristina R.
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Kristina R.
$22
total per walk
20 years of experience
Hemet, CA, 92545

About: My love for animals I've had my whole life & cared for my own furr-babies my whole adulthood, Right now I care for my own 2 beautiful furr-babie cats myself & It wasn't until a couple of years ago through my house cleaning service & the relationships I built with my customers & there pets (which I still do) has provided me the experience to care for other pets. I have experience in house/dog sitting, a lil. Dog grooming, & visits to homes to walk, feed & play with, I've dog sat with puppies as well, I have the ability & knowledge to adapt to the animals personalities (because they are all different) but more Importantly I have so much love to give to all animals. I work part-time as a housekeeper during the week days. So my availability is pretty open after 3pm on the week days & my weekends are completely open for any time of the day & I can be available for house/dog sitting as long as I know a few days ahead time I can schedule my job around it no problem. Well Every pet is different with there own personalities & with that being said, It goes without saying first & foremost you have to respect the pet, the owner & there home as well as any care specific required. In other words we have to care for them just like there one of the family members by giving them all your love & attention needed.

Sitter Profile Image: Jenny D.
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Jenny D.
$35
total per walk
5.0 out of 5 stars
• 192 reviews
45 repeat clients
40 years of experience
Menifee, CA, 92584

“First of many bookings for sure!!! Thank you for caring for our puppy!! Lots of communication and pictures through. We are very pleased and relieved that Noelle had a nice walk!”

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Raphael O.
Sitter Profile Image: Lucas S.
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Lucas S.
$23
total per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
16 years of experience
Murrieta, CA, 92563

About: What sets me apart from other care givers is the level of care and attention I give every pet. I know that every pet has a unique personality, routine, and comfort level, and I take the time to make sure they feel safe, happy, and loved while you're away. I cared for my own female hound mix from the time she was just six weeks old until she passed at 16 years old. That experience taught me how to care for a dog through every stage of life - from energetic puppy years to the special patience and gentle attention senior dogs need. I'm comfortable following feeding schedules, administering care as needed, going on walks that match a dog's energy level, and making sure pets get plenty of love, playtime, and companionship. I'm dependable, communicative, and I treat every pet as if they were my own. My goal is to give you peace of mind knowing your pet is in caring and responsible hands. Pet care is something I genuinely enjoy, and I've built my schedule to be as flexible as possible. I have availability throughout the week, including weekdays and weekends, and I'm happy to accommodate morning, afternoon, and evening visits whenever I can. Whether your pet needs a walk, a drop-in visit, or overnight care, I'll do my best to work around your schedule. I also keep my calendar updated so you can book with confidence, and I'll communicate promptly if you have any questions or special requests. My goal is to provide reliable, consistent care that fits seamlessly into both your routine and your pet's. I currently provide pet care in my clients' homes, where I focus on keeping your pet comfortable by maintaining their normal routine as closely as possible. I'll follow your instructions for feeding, walks, playtime, medications (if needed), and any other special care your pet requires. I understand that consistency helps pets feel safe while you're away, so I take the time to learn their habits, preferences, and personality. Whether your pet enjoys long walks, play sessions, or simply relaxing with company, I'll make sure they receive plenty of attention, affection, and care. I'll also treat your home with the same respect I would my own, keep everything clean and secure, and provide regular updates with photos so you can have peace of mind while you're away.

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: Valarie R.
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Valarie R.
$28
total per walk
15 years of experience
Homeland, CA, 92548

About: I have experience working with puppies and many breeds. I will reinforce desirable behaviors through positive reinforcement. I have experience giving medication. I can take your pet to the vet for you. I have many years of experience working with animals at a veterinary hospital and animal shelter/rescue. I am available short or long term. I am available week days and weekends. Caring for pets is my vocation. I don’t have any schedule restrictions I have outdoor and indoor space according to your pet’s preferences. While outdoors, your pet will be supervised in an enclosed yard. I provide opportunity for water loving dogs to play in the pet pool. I provide “nose work” for those dogs that need mental activities.

Sitter Profile Image: Belinda S.
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Belinda S.
$43
total per walk
5.0 out of 5 stars
• 25 reviews
10 repeat clients
10 years of experience
Hemet, CA, 92545

About: Hello, my name is Belinda. I have been a fur mom for 10 years and I truly love spending time with dogs. I’m able to give your dog all the attention needed, and they would never be unattended. Feel free to bring their favourite toys or let them choose from our selection.I have a large gated backyard that your dog will enjoy. All dogs will get plenty outdoor time. My days start early, so drop off and pickup times are pretty flexible. I’m not currently working, so my full time job would be caring for your pet! Flexible schedule and I offer extended stays as well. Only sitting at home I’ve got experience with it all! I’ve also administered medication to dogs of all ages and sizes. lover of all pets, young and old, big and small. ( I DONT ACCEPT PITBULLS). And for allergy reasons I don’t accept CATS We can do walks, hikes, swimming, even to a play day at the park. I Live on the west Side in a house with a fenced yard and friendly neighbours!

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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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  • 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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Meet local walkers who will treat your dogs like family

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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 on Rover is $23 per walk as of October 2026. Most bookings cost between $22 and $29 per walk. 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 October 2026, there are 3,499 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 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:

  • 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 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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