Dog Walking Stephenson

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

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Sitter Profile Image: Alexsys T.
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Alexsys T.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 374 reviews
139 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: Hannah D.
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Hannah D.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
• 107 reviews
24 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: Stephanie B.
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Stephanie B.
from
$20
per walk
32 years of experience
Winchester, VA, 22601

About: My family lives in downtown Winchester where there are plenty of places to walk. Since I am in a new season of life (semi retired) I wanted to so something I love like walk more and take care of your pet(s). I have been a dog owner for 16 years. I have trained a puppy and helped my first dog all the way through elderly care. Three cats have touched my heart, two cats from kittens through elderly stages. I offer a quiet and comforting hand to all animals. Your companion(s) are God's gift to your family and I would be honored to take care of them. I am currently working part-time for the city transportation division but have a flexible schedule so I can take care of your pet(s). I am an early riser so I don't mind those pets who need morning care. That does mean I go to bed early so I would stop at 8pm. I am a respectful semi retired lady who loves animals. My pets roam around freely at my home. They love their morning routines as I do. If I take care of your pet(s) I will keep whatever routine you have already established with love, safety, and kindness.

Sitter Profile Image: Chelsea W.
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Chelsea W.
from
$20
per walk
5.0 out of 5 stars
• 6 reviews
1 repeat client
20 years of experience
Winchester, VA, 22602

About: I have always had a deep love and affection for animals, and I am lucky enough to have three fur babies of my own. As a pet owner, I understand the importance of finding someone reliable and trustworthy to care for our furry friends while we are away. That's why I am excited to offer my services as a pet sitter. I promise to treat your pets with the same love and care that I give to my own dogs, and will make sure that they are happy and comfortable while in my care. Whether it's walking, feeding, or just providing some extra TLC, I am dedicated to making sure that your pets are well taken care of. If you are in need of a responsible and caring pet sitter, I would love the opportunity to be of service. My husband and I both work from home so we are able to provide bathroom breaks, cuddles and attention all day long for our fur guests. For drop in visits we can come during our lunch hour and right after work! I am able to provide food, medications, love, cuddles, time outside, play time, and make sure they are taken care of to the fullest extent during their visit with my family.

Sitter Profile Image: Hannah H.
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Hannah H.
from
$20
per walk
5.0 out of 5 stars
• 14 reviews
5 repeat clients
10 years of experience
Inwood, WV, 25428

“Such an amazing dog walker! My dog absolutely LOVES her. She’s always on time, caring, and attentive with our pup. We feel so lucky to have found her. I couldn’t recommend her more!”

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MattaLynn P.
Sitter Profile Image: Megan H.
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Megan H.
from
$15
per walk
5.0 out of 5 stars
• 7 reviews
1 repeat client
5 years of experience
Winchester, VA, 22601

About: I’m new to the area and looking to help out with the furry friends in my neighborhood! I’ve grown up around dogs and cats since I was young, and love getting to spend time with them, whether it be taking them on walks/runs, playing with them, or just giving them lots of love and attention. I am reliable, with my own transportation and a flexible schedule! I am a new graduate student at Shenandoah University - as a musician I have a few rehearsals in the afternoons and evenings, but my schedule is pretty open otherwise and I’ll have plenty of time to stop by/stay over and keep your pets company! I am a rule follower! I will follow your guidelines to a T, and make sure your pet is cared for exactly as you wish. I know that pets are our whole world, and leaving them with a stranger can be nerve wracking - I am reliable and responsible, and you can easily trust me to take care of your loved ones!

Sitter Profile Image: Cameron W.
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Cameron W.
from
$18
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
7 years of experience
Winchester, VA, 22601

About: I have a love and understanding for all animals! I have trained my own and have learned so much through them. I have a lot of experience with dogs with behavioral issues. I am a college student with a lot of free time. My evenings are free and I have a lot of gaps during the day! I would love to get out on walks with dogs in my gaps. I have my own dog to keep yours company if that is something you would like. If not, he can stay with his other mama when your pup is over! Dogs will get full exercise and enrichment when staying with me. We will be in a fenced in yard running around and go on serval walks throughout the day.

Sitter Profile Image: Reina P.
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Reina P.
from
$18
per walk
4.9 out of 5 stars
• 29 reviews
9 repeat clients
10 years of experience
Boyce, VA, 22620

About: Hi, My name is Reina, I recently retired and love to care for pets. I have a lot of time and dedication to care for yours. Flexible with schedules. I am currently retired, so I have a lot of time to play and properly care for your pet. I do not have pets anymore since my sweet dog passed away.I am ready to give the same kind of love and attention to yours. I have a fence yard and a very clean environment.I do not have pets anymore since my sweet dog passed away.I am ready to give the same kind of love and attention to yours.

Sitter Profile Image: Emily F.
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Emily F.
from
$16
per walk
6 years of experience
Winchester, VA, 22601

About: Available in evenings and weekends. I am reliable, responsible and always on time. I love all dogs and I appreciate all the quirks that come with their individual personalities. I have loved animals since I was young, and I volunteered for a pet shelter in the summer when I was younger. Although I am currently a cat owner, I love all furry animals and I have to greet every dog I meet on the road. I am looking for part time work and this would be a great opportunity to utilize my free time and my love for canines and kitties. I have three cats that are basically like my children, but I adore dogs and would love the opportunity to interact with them daily or weekly. I have free time on my work from home days as well as weekends to assist other dog/cat owners. I do not have a fenced yard, but I live in a community that has a lot of pathways and green space. Within my apartment, I can keep my cats separate if needed but happy to let the dogs explore and get comfy in my space. I am very courteous of other people's space and preferences.

Sitter Profile Image: Day B.
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Day B.
from
$25
per walk
4.9 out of 5 stars
• 66 reviews
25 repeat clients
20 years of experience
Charles Town, WV, 25414

“Day is a true animal lover. My dog, Buddy and cats Phantom and Mouse were immediately drawn to her. She was there for me at a last minute dog walking request and helped me out by ensuring that my furry friends were well taken care of. I am so grateful to have found a devoted animal lover.”

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Heidi Z.
Sitter Profile Image: Courteney B.
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Courteney B.
from
$30
per walk
5.0 out of 5 stars
• 5 reviews
12 years of experience
Winchester, VA, 22601

About: I cared for my family dog for 12 years until she passed, as well as cared for my family and friends furry animals over the years. Hi! Im a new mom, currently have more availability as I’m on leave. Once returned to work, I can be available during lunch time or after 430pm m-f during weekdays. Weekend schedule is flexible and open. I’ll make sure they are safe at all times, and well taken care of. Take them on walks, feed them if needed, and play of course!

Sitter Profile Image: Stefany P.
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Stefany P.
from
$45
per walk
3.7 out of 5 stars
• 3 reviews
5 years of experience
Winchester, VA, 22602

About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)

Sitter Profile Image: Kathleen M.
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Kathleen M.
from
$15
per walk
5.0 out of 5 stars
• 5 reviews
10 years of experience
Inwood, WV, 25248

About: I have over 10 years experience in both dogs and cats. I have raised two of our family dogs and I own two cats. I have so many tips and tricks and I would love to send you all the photos of your babies! I currently have full and open availability to help with you special family pet! I can do anything you need at any part of the day. I would love to walk your puppy, clean out litter boxes, or just hang out with your pet so they aren’t alone! I do have three cats so unfortunately I can not bring your dog into my home. I am willing to stay at your place for however long and I will send daily photos of your pets!

Sitter Profile Image: Liberty W.
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Liberty W.
from
$25
per walk
5.0 out of 5 stars
• 142 reviews
48 repeat clients
15 years of experience
Charles Town, WV, 25414

“The ease of working with Liberty was commendable. She was very communicative and us informed. She asked probing questions pertinent to making the walks with Kyoshi worry-free. Further, she was very attentive especially on Kyoshi’s triggers such as squirrels and stuff on the ground. Kyoshi had a great time with Liberty, and would he more than happy to bond again with her in the future! Thank you very much, Liberty! We greatly appreciate the genuine attention and care you gave to Kyoshi!”

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Maria A.
Sitter Profile Image: Melissa A.
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Melissa A.
from
$20
per walk
5.0 out of 5 stars
• 26 reviews
8 repeat clients
40 years of experience
Cross Junction, VA, 22625

About: Hi there, My name is Melissa and I work from home which allows me to have a very flexible schedule. l am a very active person who absolutely loves all sorts of fur babies, especially dogs and cats. I enjoy having the ability to interact with them on a daily basis. I currently have one fur baby of my own, Roxy (13 yo Jack Russell), but I have been around all types of animals since I was little, and I can't imagine my life without them. I would love to include more animals in my life by helping you take care of yours from drop-in visits, dog walking and more! I believe in positive reinforcement training versus negative reinforcement, which supports an animal’s overall well being. My goal is to make sure that your dog is fully sated from our walk so that when you get home you have a relaxed doggie! Having had more than one dog of my own in the past I am experienced in walking multiple dogs at a time, so if you have 2 or more dogs that need daily walks I am up for it! Also, if your pet just needs a cuddle and some caring for during the day I am happy to drop in visit on them and spend some time with them! I hope you’ll consider me for your pet care needs. I promise to treat your fur baby as if it were my own! Looking forward to working with you and your fur babies. I am have a very flexible schedule for dog walking and pet drop-in visits. Morning, afternoon or night time, I would be happy to take care of your pets! I will treat your fur baby as if they were my own pet with respect and gentle care. I also will respect your household and leave it in the condition it was in when I arrived.

Sitter Profile Image: Jessica M.
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Jessica M.
from
$30
per walk
25 years of experience
Winchester, VA, 22601

About: Hello, pet parents! My name is Jessica, and I bring over 25 years of dedicated experience working with both dogs and cats. As a professional dog groomer for the past 15 years, I have developed a keen eye for pet care and well-being. At home, I share my life with a delightful trio: a standard poodle, a lovable pit bull, and a majestic Maine coon cat. Each of them has taught me unique lessons in care, patience, and the joy of pet companionship. Why choose me? • Decades of Experience: With 25 years of hands-on experience, your pets are in knowledgeable and capable hands. • Groomer’s Expertise: My grooming background ensures your dog not only gets a great walk but also some extra TLC, including coat checks and paw care. • Personalized Care: I understand that every pet is unique. I tailor my services to meet the specific needs and personalities of each furry friend. • Safety First: Your pet’s safety is my top priority. I am trained to handle various breeds and temperaments with care and professionalism. Let me provide your pets with the exercise, attention, and love they deserve. Book a walk today and see the difference an experienced and passionate pet professional can make! I’m a professional dog groomer with a flexible schedule that allows me to provide dog walks and drop-in visits throughout the week. I enjoy using my available time to give pets the exercise, attention, and dependable care they need while their families are away. Your pet’s safety and comfort are my priority. With 25+ years of experience caring for dogs and cats and 15 years as a professional dog groomer, I’m comfortable working with pets of many breeds, sizes, ages, and personalities. During drop-in visits, I can provide potty breaks, feeding, fresh water, playtime, and medications as directed. I also offer dog walks tailored to your pet’s individual needs.

Sitter Profile Image: Ruby K.
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Ruby K.
from
$20
per walk
5.0 out of 5 stars
• 2 reviews
10 years of experience
Winchester, VA, 22602

About: I’ve always loved caring for pets starting from when I was a kid growing up around them. In my teen years, I began pet sitting and walking dogs for neighbors and friends, gaining hands-on experience and learning what each furry friend needs to feel happy and safe. I’m dedicated to providing loving, trustworthy care, making sure every pet gets the attention and kindness they deserve while their owners can have peace of mind. I have a very flexible schedule and can easily work around walking and sitting times, but I especially prefer weekend house sitting to give your pets the best care when you’re away. Walking is more flexible as I can do it everyday. With my experience, I’m prepared for any unexpected situations that might come up during pet sitting. I stay calm and trust my instincts to make sure your pet stays safe, comfortable, and cared for right in your home.

Sitter Profile Image: Chelsea S.
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Chelsea S.
from
$24
per walk
5.0 out of 5 stars
• 7 reviews
4 repeat clients
20 years of experience
Charles Town, WV, 25414

“She took great care of my dog. Would recommend her to anyone.”

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MattaLynn P.
Sitter Profile Image: Cortni B.
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Cortni B.
from
$25
per walk
12 years of experience
Inwood, WV, 25428

About: Grew up with Dachunds, then had 3 large dogs during marriage now I have the youngest one left with me Baylee May about 6 yrs old. I often dog sat for multiple friends and family. I am very flexable. I do not currently have a full time job and only am busy when my step children need to be taken to school in the mornings, but even that only takes an hr out of my day. I am extremely reliable and trustworthy. I value and respect peoples homes, items and ofcourse their pets. I would always treat every pet the way I expect people to treat mine. I can provide refrences if needed.

Sitter Profile Image: Rachel R.
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Rachel R.
from
$20
per walk
30 years of experience
Charles Town, WV, 25414

About: I’ve had dogs of my own my whole life. I’ve been taking care of others’ dogs for many years. I have experience with various breeds and sizes. Willing to do occasional jobs or recurring ones. I had to put set prices into my profile, but willing to discuss. I’m currently working part time and have a very flexible schedule. I am available any weekday and, with notice, can be available on weekends as well. I do not provide care in my home, but would love to come to your home where your dogs are most comfortable. I will provide any care needed- letting out in a fenced yard, taking for walks, feeding, administering meds, etc.

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

Dog parents share their Rover experiences - Stephenson

1 / 1
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
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How to book dog walking

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Sitters in Stephenson average 3
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FAQs for Dog Walking - Stephenson

Frequently asked questions about Rover

The average cost of Dog Walking in Stephenson is $22 per walk as of November 2026. Most bookings cost between $17 and $28 per walk. On Rover, 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 November 2026, there are 846 sitters on Rover offering Dog Walking across Stephenson. 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 Stephenson. 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 Stephenson 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 Stephenson. On Rover:

  • 92% of walkers can help with special care needs
  • 95% 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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