Dog Walking in Winchester

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

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Top rated Winchester dog walkers

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Kimberly B.
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Kimberly B.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
318 reviews
111 repeat clients
8 years of experience
Winchester, VA, 22601

We’ve hired Kim a few times to feed and walk our dog. She is very reliable and friendly and takes great care of our dog. The Winchester community is lucky to have someone like Kim to look after our pets :)

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Robert F.
Sitter Profile Image: Hannah D.
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Hannah D.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
82 reviews
19 repeat clients
10 years of experience
Winchester, VA, 22602

⭐️⭐️⭐️⭐️⭐️ A True Gem – Like Family to Us and Maximus! We feel incredibly lucky to have found Hannah—she’s not just a dog walker, she’s part of our family. Our dog Maximus is truly our baby (especially now that our kids are grown and out of the house), and knowing that Hannah cares for him with the same love and attention we do means the world to us. Hannah has been with us for over three months now, and in that time she’s become someone we fully trust with our most spoiled and beloved family member. She’s reliable, flexible with our crazy schedule, and always greets Maximus with affection and warmth. You can tell she genuinely loves what she does. Maximus absolutely adores her! She goes above and beyond to make sure he feels cared for when we’re not home, which gives us such peace of mind. We treasure Hannah and everything she does for our family. If you’re looking for someone who will love your dog like their own, look no further. She’s truly one of a kind.

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Gigi F.
Sitter Profile Image: courtney b.
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courtney b.
from
$17
per walk
5.0 out of 5 stars
46 reviews
14 repeat clients
20 years of experience
Winchester, VA, 22601

She was fantastic. Both my boys like her I would recommend her to anyone with any size dog.

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Brian H.
Sitter Profile Image: Suellen W.
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Suellen W.
from
$18
per walk
2 years of experience
Winchester, VA, 22601

About: I’ve had dogs my entire life, and got into dog training 2 years ago. I assisted a dog training company with the dogs they would board and care for, and assisted with multiple training outings. I also raised and trained my own service animal. I’m currently working part time, and will focus solely on providing care for your pet and home. They are my number one priority and love to do things with them. I will take them on long walks and do training with them to get their brain going. I’ll make sure their meals are extra tasty and made with love.

Sitter Profile Image: Lisette R.
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Lisette R.
from
$15
per walk
5.0 out of 5 stars
78 reviews
32 repeat clients
6 years of experience
Winchester, VA, 22601

Lisette is great with my dogs! We have an older dog that she comes and walks and he loves it. We also just got a puppy and she has been coming over in the middle of the day to take him and our older dog on small walks and it’s been great!

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Kylie J.
Sitter Profile Image: Kathy G.
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Kathy G.
from
$25
per walk
5.0 out of 5 stars
58 reviews
18 repeat clients
30 years of experience
Winchester, VA, 22601

About: I have been an animal lover & owner my entire life. I've always had a dog along with the occasional hamster, cat, guinea pig, lizard, hermit crab, rabbit, bird & fish. I love animals especially dogs. I am very comfortable with large breed dogs as well as smaller dogs too. I like to think the bigger the dog the more loves & cuddles you get.🥰 I've volunteered for rescues over the past 10 years & have fostered both dogs & cats. I'm very excited to meet new animals and their owners. I currently have 1 dog & 3 cats. I try to stick to your animal's schedule so they continue with their normal routines. I make sure your animal is given lots of attention & play time. I will show your animal affection & lots of play time & snuggling if they enjoy that. I've never met a dog that hasn't liked me....big or small.

Sitter Profile Image: Autumn P.
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Autumn P.
from
$17
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
15 years of experience
Winchester, VA, 22601

About: Hi! I’ve been an animal lover my entire life and have always had pets of my own. I worked as a kennel technician for 2 years and later as a veterinary technician for almost 2 years, where I gained hands-on experience caring for dogs and cats of all ages, temperaments, and medical needs. My background means I’m comfortable recognizing signs of stress or illness, administering basic medications, and providing calm, attentive care. While I’m no longer working in a clinic setting, the knowledge and experience I gained continue to guide how I care for every pet. I treat every animal like they’re my own — with patience, love, and close attention to their individual needs. Whether your pet loves playtime, long walks, or just quiet cuddles, I’m here to make them feel safe and happy while you’re away. I work during the week, so I primarily book weekends to give pets my full attention. When in my care, your furry friend gets walks, playtime, cuddles, and lots of love — all on a schedule that keeps them happy and comfortable. ❤️ I am available for drop ins/ walks during the week around lunch time and Fridays for boarding after 5pm! I treat every pet like family. Whether in my home or yours, they get a safe, cozy space, fresh water, walks, playtime, and plenty of love. I follow their routine and give updates so you know they’re happy and comfortable. ❤️

Sitter Profile Image: Hailey C.
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Hailey C.
from
$15
per walk
10 years of experience
Winchester, VA, 22602

About: I have been a pet owner for as long as I can remember. I have had both dogs and cats and love them both equally. I have cared for pets for both family members and friends. I've watched all types of animals with many different personalities. On top of pet sitting, I have fostered multiple litters of kittens, which has taught me patience and attentiveness. In my free time, I also enjoy volunteering at a local rescue to help walk dogs. I understand the hard work, attention and love that goes into managing any kind of animal, and I am willing to do just about anything to make sure that your pet feels loved and safe. I am a grad student who only has in person classes on Tuesday typically 8am - 4pm, which makes me very flexible for the rest of the week. I am very conscious about safety when it comes to walk, and/or letting dogs out in a fenced in area. I am sure to read any instructions before hand to learn about any issues individual pet needs.

Sitter Profile Image: Sophia M.
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Sophia M.
from
$18
per walk
5 years of experience
Winchester, VA, 22601

About: Animals have always been a huge part of my life. I currently have 4 cats and a 4-month-old puppy, so I understand the patience, attention, and love pets need every single day. Growing up surrounded by animals taught me how to care for pets with different personalities, energy levels, and needs. From playful puppies to independent cats, I’m comfortable handling feeding schedules, walks, playtime, cleanup, and giving pets lots of affection and attention. I treat every pet like family and always make sure they feel safe, loved, and comfortable while their owners are away. I currently work a flexible part-time job, which gives me plenty of time throughout the week to care for pets and give them the attention they deserve. Since I also have 4 cats and a 4-month-old puppy of my own, pet care is already a big part of my daily routine. Caring for animals comes naturally to me, and I enjoy spending my free time with them. I make sure every pet feels safe, comfortable, and cared for whether I’m in my home or a client’s home. I pay close attention to each pet’s personality and needs, whether they’re energetic, shy, young, or older. In a client’s home, I always follow instructions carefully to keep pets on their normal routine and help them feel as stress-free and comfortable as possible while their owner is away.

Sitter Profile Image: Charissa L.
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Charissa L.
from
$17
per walk
5.0 out of 5 stars
14 reviews
4 repeat clients
15 years of experience
Winchester, VA, 22601

Charissa has been great to work with! Glad we found her.

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Ellen D.
Sitter Profile Image: Kayla O.
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Kayla O.
from
$20
per walk
5.0 out of 5 stars
11 reviews
2 repeat clients
15 years of experience
Winchester, VA, 22601

About: Hi! My name is Kayla, and I've been a lifelong lover and caretaker of dogs and cats. Throughout my life, I’ve had the pleasure of caring for a wide variety of dogs, from tiny Pomskies to robust Rottweilers, and everything in between, from playful puppies to wise seniors. At home, my husband and I have a lively little boy and two wonderful fur babies. Mila, our 8-year-old pitbull, is full of sass, while Kain, our 6-year-old American bully, believes there's no such thing as too much attention. Both are high-energy and absolutely adore people. With my extensive experience and a home full of love and energy, I understand the diverse needs and personalities of pets. I look forward to meeting your furry family members and providing them with exceptional care! I'm a dedicated stay-at-home mom with a great amount of flexibility to cater to your pet's needs. Pet care fits seamlessly into my daily routine, allowing me to give your furry friends the attention and care they deserve. I specialize in drop-in visits and dog walking, ensuring your pets are well-looked after in the comfort of their own home. Whether it's a midday walk or a quick check-in, I'll make sure your pets are happy, healthy, and engaged.

Sitter Profile Image: Kayla H.
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Kayla H.
from
$24
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
21 years of experience
Winchester, VA, 22601

Kayla is so awesome! She’s professional and great with my dog. Her cancellation policy is flexible too which is super helpful. Highly recommend Kayla as a dog walker!

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Kathleen H.
Sitter Profile Image: charlotte g.
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charlotte g.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
8 years of experience
Winchester, VA, 22601

About: I have been caring for friends and neighbors dogs, cats, and small animals since i was 13. I also volunteer at the PWC Animal Shelter! i am a freshman music major at shenandoah university. i have a decent amount of availability to care for your pets every day. i have a pretty relaxed schedule. i have lots of experience with pet care and your animals will have my full attention throughout the visit. i make sure to provide your pets with adequate enrichment and play and overall care.

Sitter Profile Image: Shaghayegh H.
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Shaghayegh H.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
188 reviews
50 repeat clients
15 years of experience
Winchester, VA, 22602

My dog is very cautious around new people and Shaghayegh has been wonderful with him! She has taken time to get to know his quirks and listened carefully to all recommendations and instructions I have given her in regards to and how to deal with his shyness. She clearly loves dogs and really makes an effort to make their experience enjoyable when they are with her. I highly recommend her!

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Kristin P.
Sitter Profile Image: Alexsys T.
Verified Enhanced Background Check
Alexsys T.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
304 reviews
118 repeat clients
7 years of experience
Clear Brook, VA, 22624

Alexsys is awesome. Communicative, thorough, and sends me all the updates and photos I need when I’m away. She even sent a picture of my porch kitty!

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Jenelle B.
Sitter Profile Image: Jose O.
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Jose O.
from
$15
per walk
6 years of experience
Winchester, VA, 22602

About: Hi my name is Jose Alfredo and I can be very laid back and socially outgoing with a fun and friendly personality! I love being around friendly pets and I was a previous cat owner for 4 years. I also used to share my place with my close friend and his dog of 3 years who I helped care for many times. I have other family members and friends who have pets as well and I have been around them long enough to love and know me. I have spent a lot of time around other people's dogs most of my life and have great experience with both dogs and cats. Being around other people's pets over time has given me the opportunity to know and understand different dog and cat personalities and each ones individually unique needs and traits. Book me and I will walk your dog, feed it, play with it and make sure it has gone to the bathroom. I will tend to your cats' need as well and make sure it's fed, hydrated and help maintain it's litterbox's cleaniliness and given lots of attention! I am also willing to help with small house chores like taking out the trash, bringing the bin to the front, watering your plants or any other simple house duties for no extra charge! At the moment I will go to you to take care of your pet in your home so you don't have to worry about putting your pet in a new environment it's not used to. I will make sure everything in your home is as tidy as before I even arrived. As long as you can provide me with the proper details and instructions about your pets' needs, where things are and how to get in and out of the house, then I promise you everything will be done as requested. As a way of building trust, we will arrange to do a proper meet and greet at your home or a public place like the park. This is so me and your pet can get familiar with each other, earn trust between owner and sitter, and have comfortability and assurance that your pet and home will be in good hands. Thank you for choosing me to care for your pets! I am currently flexible with availability for most days of the week as I do not have any other full time job at the moment. However, I currently am a student studying full-time and sometimes get involved in campus events, extracurriculars, and other student organizations. So Tuesdays and Thursdays I'm typically more busy with classes. But as long as the requested time works around my schedule and classes then we can make it work and I can be available whenever I am not spending time on campus. I do prefer to be notified at least 3 days in advance for requests but I am also willing to take up to same day bookings as long as I am completely free for that day, but it is not guaranteed. But please do try to reach out and book with me in advance at first if possible. I also prefer to schedule a meet and greet prior to accepting booking requests for new first time clients. But I will be more than happy to work with you so I can make a new furry friend if we are a great fit for each other! I used to play with my roommate's dog every day and feed him or take him outside to potty when the roommate was not around or unable to. I play ball with his dog, tug of war and give him belly rubs. His dog is also very attached to me as I am to him. I also was a cat owner for 4 years who I took care of every day from feeding him to ckesning his litterbox and playing with him. I hope to form this same kind of relationship with your pet!

Sitter Profile Image: Karen O.
Verified Enhanced Background Check
Karen O.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
19 reviews
9 repeat clients
12 years of experience
Winchester, VA, 22602

Karen is the best! Bentley loves her. She takes her time and really cares about your pet. Thanks Karen you’ve been amazing to work with.

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Dana M.
Sitter Profile Image: Isabella M.
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Isabella M.
from
$20
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Winchester, VA, 22601

About: I have had animals in my life since I was born. Animals including dogs, cats, hamsters, birds, fish and even a chameleon. I love animals and have a lot of experience with many different kinds! I am a teacher who is off for the Summer and looking to fill my time taking care of some fur babies! 🐾 I am a teacher who is off for the Summer! I work 8-4 during the school year so when school is back in session I will be available to check in on pets after school hours! I love animals and enjoy playing with and spending time with them. I love to play with my cats Bootsie and Penelope and can’t wait to meet your animals!

Sitter Profile Image: Alex M.
Verified Enhanced Background Check
Alex M.
from
$15
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Winchester, VA, 22601

About: I have owned and trained dogs most of my life, grew up on a farm with all types of pets and find it second nature to treat them like family. I currently work from home and have a very flexible schedule. I can house sit, drop in or stay with your pet as long as you need someone. My dog has a fenced in yard and is at day care for socialization M-F so I can have my full attention on your dog. I currently work from home part time so I have plenty of time for your pet! I am awake early and have a flexible schedule to fit yours. I make sure you and your pet are comfortable with me and follow instruction when caring for your pet. You know your pet best and I want them to be happy and content with me.

Sitter Profile Image: Sierra B.
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Sierra B.
from
$15
per walk
4.8 out of 5 stars
21 reviews
9 repeat clients
10 years of experience
Winchester, VA, 22602

Sierra got along well with my standoffish Akita, Bailey. She was on time, and let me know what Bailey did on her walks. I would highly recommend Sierra!

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Robin R.
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Over 297
pet parents in Winchester have booked dog walking

Winchester dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Thanks as always Alyssa. Yeah anytime the weather is hot, bring him in as soon as he does his business. You see he likes the fan on! Great job 👏

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James H.
Dog Walking
5.0 out of 5 stars

Kimberly takes such good care of Tucker. She always gives a detailed description of there time together. Thanks Kimberly 👍 A+++

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James H.
Dog Walking
5.0 out of 5 stars

Thank you so much for walking Willow on such short notice! I really appreciate your help and how you went above and beyond by also giving her fresh water after the walk 😊

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Heaven A.
Dog Walking
5.0 out of 5 stars

Absolutely fantastic! On time, thank ok good care of my girl and accepted in a moments notice! Definitely will be using Alexsys again!

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Robert S.
Dog Walking
5.0 out of 5 stars

James is excellent. So great in so many ways What a blessing when my back went out. James saved the day for 4 days!

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Manley N.
Dog Walking
5.0 out of 5 stars

Karen is the best! Bentley loves her. She takes her time and really cares about your pet. Thanks Karen you’ve been amazing to work with.

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Dana M.
Dog Walking
5.0 out of 5 stars

Gabriel was a life saver for my husband & I. Super responsive, great with our little dog, very trustworthy. Highly recommend :)

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Christina G.
Dog Walking
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The median cost per walk for dog walking in Winchester is $20

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Sitters in Winchester average 3
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Winchester on Rover as of Jun 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

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

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

As of Jun 2026, there are 541 dog walkers in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 84% of Winchester dog walkers respond in under an hour.

Dog walkers in Winchester have an average of 16 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Winchester.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 541 dog walkers in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 95% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.