Dog Walking in Winchester

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

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

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.

1 / 1
Sitter Profile Image: Kimberly B.
Verified Background Check
Kimberly B.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
288 reviews
106 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 :)

Profile image
Robert F.
Sitter Profile Image: Hannah D.
Verified Background Check
Hannah D.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
63 reviews
16 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.

Profile image
Gigi F.
Sitter Profile Image: Lisette R.
Verified Enhanced Background Check
Lisette R.
from
$15
per walk
5.0 out of 5 stars
73 reviews
27 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!

Profile image
Kylie J.
Sitter Profile Image: Charissa L.
Verified Enhanced Background Check
Charissa L.
Star Sitter
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.

Profile image
Ellen D.
Sitter Profile Image: Alexsys T.
Verified Enhanced Background Check
Alexsys T.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
270 reviews
104 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!

Profile image
Jenelle B.
Sitter Profile Image: Karen O.
Verified Enhanced Background Check
Karen O.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
13 reviews
5 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.

Profile image
Dana M.
Sitter Profile Image: courtney b.
Verified Enhanced Background Check
courtney b.
from
$17
per walk
5.0 out of 5 stars
43 reviews
12 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.

Profile image
Brian H.
Sitter Profile Image: Susan B.
Verified Enhanced Background Check
Susan B.
from
$15
per walk
15 years of experience
Winchester, VA, 22601

About: I’ve loved animals my whole life, and I’ve had the pleasure of living with, and pet sitting for multiple cats and dogs. I’ve done both kitty and dog meds, so if you have a high maintenance fur child like me, I’ve got you covered!! If you trust me with your fur baby, I promise I will love them as much as I love my own!! I work from home, so I have a lot of flexibility. Mornings are more difficult for me, but I can definitely work with you to find what’s best for the pets! My own pets are high maintenance, so I am definitely able to work with your pets needs. I crate my own dog, and give both my dog and cat meds and supplements. I don’t have any human children so my pets are my children. I will give your pet the love, attention, and care I give my own!!

Sitter Profile Image: Myahrissa R.
Verified Enhanced Background Check
Myahrissa R.
from
$20
per walk
5.0 out of 5 stars
127 reviews
26 repeat clients
4 years of experience
Stephenson, VA, 22656

Myahrissa is fabulous! It’s really comforting to know my girl is in good hands when we have scheduled walks with her. I get the cutest pictures, detailed updates, and I always come home to a happy little wiggle butt of a dog. Every visit / communication feels as though she genuinely loves spending time with my girl as much as I do and as a pet parent, that’s all I could ever ask for.

Profile image
Brittany C.
Sitter Profile Image: Sadie S.
Verified Enhanced Background Check
Sadie S.
from
$18
per walk
5.0 out of 5 stars
12 reviews
2 repeat clients
5 years of experience
Winchester, VA, 22601

About: My name is Sadie. I am an 20 year-old, graduate student, at Shenandoah University. I love hanging around dogs, cats, or honestly any animal. I have been exposed to all types of animals from farm to regular housepets. I was raised living with a cat and taking care of chickens. I also would help out neighbors with watching their pets; started doing so around the age of 12. I have quite a few experiences under my belt with dogs ranging from 5 month olds through veterans. My dog is an American Pitbull Terrier and is now 3 years old. I love him and any animal I am responsible for with all I have. When I am home from school, I am more than likely open to any schedule. Most likely what works for you, will work for me! As of right now, I do have another part-time, low hour job and internship. Even with those two, I have plenty of free time to come help you with your pets! Your pets will be cared for by me just as much as you do for them. I am a hard worker who will always give 110% into caring for your pets. Whatever you ask of me to do, I will do my best to complete to your and your pets' satisfaction. I also will provide you with pictures and updates whenever your pets and I do anything.

Sitter Profile Image: Kayla H.
Verified Enhanced Background Check
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!

Profile image
Kathleen H.
Sitter Profile Image: Sophia C.
Verified Enhanced Background Check
Sophia C.
from
$20
per walk
10 years of experience
Winchester, VA, 22603

About: What sets me apart is my presence and intention. I don’t rush walks or treat them like a checklist. I’m doing this because I genuinely miss having a dog in my daily life and want to build consistent time outdoors, which means your dog gets my full attention—not just exercise, but engagement and care. I’m naturally attentive, calm, and detail-oriented, so I’m very mindful of leash safety, surroundings, and your dog’s comfort level. I’m especially patient with shy dogs or those who need a slower, more relaxed pace, and I’m happy to follow any routines or preferences you have. While I may be newer to professional dog walking, I take reliability and communication seriously. I’ll keep you updated, respect your home, and treat your dog with the same care I would want for my own. Pet care fits naturally into my routine. I work nursing shifts three days a week, which gives me four open days where I’m not juggling another work schedule. On those days, I have the flexibility to plan my time around walks, drop-ins, and consistent routines rather than squeezing them in. Because of this structure, I’m able to be punctual, unrushed, and dependable. Since I primarily offer dog walking, my focus is on providing safe, attentive, and positive walks tailored to each dog’s needs. I tailor each walk to your dog’s energy level, walking style, and any preferences you have before we head out, while also paying close attention to leash safety, pacing, and surroundings In a client’s home, I’m respectful, clean, detail-oriented, following all instructions closely. My goal is for you to feel confident that your pet is cared for with the same attention and care I’d want for my own.

Sitter Profile Image: Alyssa F.
Verified Background Check
Alyssa F.
from
$15
per walk
4.9 out of 5 stars
55 reviews
9 repeat clients
7 years of experience
Winchester, VA, 22601

Thanks Alyssa. When we are walking Tucker and I always stop and let people walk past. Just to keep everyone at ease. Not all dogs are as friendly as our boy. Tucker was acting out of respect.

Profile image
James H.
Sitter Profile Image: Mark R.
Verified Enhanced Background Check
Mark R.
from
$24
per walk
5.0 out of 5 stars
5 reviews
35 years of experience
Winchester, VA, 22601

The BEST. Patient,kind and reliable..Highly recommended.

Profile image
Lynne F.
Sitter Profile Image: Shaghayegh H.
Verified Background Check
Shaghayegh H.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
185 reviews
49 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!

Profile image
Kristin P.
Sitter Profile Image: Zoe A.
Verified Enhanced Background Check
Zoe A.
from
$20
per walk
10 years of experience
Winchester, VA, 22602

About: What sets me apart is my depth of experience and adaptability! I’ve been house-sitting and providing full-time pet care for several years, both short- and long-term, in a wide variety of homes, from apartments to multi-animal properties. I’m comfortable caring for pets of all ages and needs, including puppies, seniors, and animals requiring medications (like ear and eye drops, pills, and ointments) or special routines. I have hands-on experience with cats and dogs of all ages, so I’m confident following detailed care instructions for many species. Because I often stay in the home while caring for pets, I prioritize consistency, cleanliness, and communication. I maintain pets’ normal routines, keep homes well cared for, and provide regular updates so owners can travel with peace of mind. I’m calm, observant, and proactive; if something seems off, I notice quickly and act responsibly. Above all, I treat every pet as an individual and every home with respect. My goal is always for pets to feel safe, comfortable, and genuinely cared for while their humans are away! I work remotely Monday through Friday, typically from 9 AM–5 PM, which allows me to be home with pets throughout the day rather than away at an office. My work is flexible, so I can easily schedule walks, feedings, medication, playtime, and check-ins around pets’ routines. I’m able to take brief breaks during the day for potty breaks, enrichment, and companionship, and I’m fully available in the mornings, evenings, and weekends. For house-sitting stays, I prioritize maintaining each pet’s normal schedule so they feel comfortable and secure. Because I’m often in the home, pets get consistent supervision, attention, and care, not just quick drop-ins. I’m happy to adjust my routine for puppies, seniors, or pets with special needs. I provide pet care exclusively in my clients’ homes, where pets are most comfortable and routines stay consistent. I do not offer care in my own home. Safety and trust are always my top priorities. I carefully follow all written and verbal care instructions, including feeding schedules, medications, exercise routines, and household rules. I keep doors, gates, and enclosures secure, monitor pets closely for any changes in behavior or health, and address issues promptly and responsibly. I maintain a clean, calm environment, respect each home as if it were my own, and ensure pets are supervised appropriately based on their age, temperament, and needs. I’m experienced with multi-pet households and mixed species and take extra care to manage interactions safely. I communicate regularly with updates and photos so owners feel confident their pets and home are in good hands while they’re away.

Sitter Profile Image: Joshua H.
Verified Enhanced Background Check
Joshua H.
from
$25
per walk
5.0 out of 5 stars
5 reviews
3 repeat clients
25 years of experience
Winchester, VA, 22601

About: I’ve been around both cats and dogs since I was a baby. From my first cat, Deedle, and my famous boxer, Satch, I love the companionship animals bring. I recently had to put down my best friend, Sadie; a black lab/chow mix that I adopted when she was 6 months old and I was 19 (I’m 37). I’m not allowed to have dogs in my complex so I take every opportunity to be around them when I can. I’ve never run into a dog (or cat) that didn’t have an instant bond with me, so this opportunity is perfect for all of us. I’m currently in between jobs and am located in a very accessible place. For the time being, I’m readily available to take care of your furry family. Animals are usually drawn to me, so I have no problem giving them the attention they need and deserve. I’ve also gotten very good at reading them, so for those that like their space, I just make sure to be available and that they are taken care of if anything is needed.

Sitter Profile Image: Alex H.
Verified Enhanced Background Check
Alex H.
from
$18
per walk
5.0 out of 5 stars
20 reviews
9 repeat clients
10 years of experience
Winchester, VA, 22601

Alex has been great with our dogs! He goes above and beyond and our dogs do so great with him! I would definitely recommend Alex. He has a great attitude and works well with different breeds. We have a pitbull and an Australian Shepherd, and they really love Alex and look forward to their time with him!!

Profile image
Tammy S.
Sitter Profile Image: Meghan H.
Verified Background Check
Meghan H.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
582 reviews
302 repeat clients
24 years of experience
Stephens city, VA, 22655

Meghan is amazing! My 6 year old mini golden doodle never had a babysitter she didn’t know previously, and I was so nervous going out of town and leaving her. Meghan was so responsive and professional- I felt so much more at ease after talking with her! I got photos of their walk together and it made me so happy to see my dog having so much fun!

Profile image
Olivia D.
Sitter Profile Image: Amy P.
Verified Background Check
Amy P.
from
$12
per walk
5.0 out of 5 stars
2 reviews
2 repeat clients
10 years of experience
Winchester, VA, 22601

Thanks for walking my dogs and meeting them before the scheduled walks. I really appreciated that. It's clear from the pics that my dogs enjoyed the walks with you. ❤

Profile image
Harjeet K.
1 / 1
View more sitters

Over 290
pet parents in Winchester have booked dog walking

Winchester dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Thanks Alyssa. When we are walking Tucker and I always stop and let people walk past. Just to keep everyone at ease. Not all dogs are as friendly as our boy. Tucker was acting out of respect.

Profile image
James H.
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!

Profile image
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!

Profile image
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.

Profile image
Dana M.
Dog Walking
5.0 out of 5 stars

Kim is great! She walked, visited, and played with my sweet boy who had to stay home when I went to work. He has separation issues (he’s a rescue) and having her visit gives me peace of mind. She sends me pictures and updates that makes me feel happy knowing he’s getting a visit from Kim!

Profile image
Lauren H.
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 :)

Profile image
Christina G.
Dog Walking
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a dog walker who’s a great match for you and your dog
  2. 2. Meet & Greet

    Meet either virtually or in-person with a walker to discuss the level of care needed for your dog
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your dog walker has to cancel, we’ll work with you to find a new walker.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

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 Mar 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 Mar 2026, there are 558 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 558 dog walkers in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 91% 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.