Dog Walking Winfrey

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Winfrey, Find top rated dog walking

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: Stephanie H.
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Stephanie H.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
40 reviews
23 repeat clients
35 years of experience
Culpeper, VA, 22701

Stephanie is everything you could hope for in a dog walker—she’s communicative, responsive, careful, dependable, and genuinely caring. You can truly tell she loves what she does, and it shows in how she treats the dogs in her care.

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Hannah R.
Sitter Profile Image: Katie G.
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Katie G.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
41 reviews
9 repeat clients
10 years of experience
Culpeper, VA, 22701

Katie does an amazing job with my dog! She asks detailed questions and makes sure she knows all about my dog’s quirks. Highly recommend her and my dog loves her!

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Hannah S.
Sitter Profile Image: Jessica W.
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Jessica W.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
42 reviews
17 repeat clients
15 years of experience
Culpeper, VA, 22701

About: *** I wanted to let everyone know that I’ve made the difficult decision to step away from dog sitting through Rover for the remainder of 2026 as I navigate some significant personal life changes. I deeply appreciate all of the support, trust, and loyalty from my clients and their beloved pets over the years. Thank you for everything. ❤️ *** Animals—especially dogs—are my passion! I have over a decade of experience pet-sitting and grooming dogs, and have owned, fostered and cared for dogs, cats and exotic pets of all breeds and sizes in my home since I was very young. I have always been particularly passionate about caring for and working with dogs. I am the proud owner of two Australian Shepherds, who I enjoy training in behavior and agility. If you're in need of someone who is loving, patient and trustworthy to look after your dog(s), please don't hesitate to reach out! I look forward to having the opportunity to care for your beloved fur babies, and promise to love them like they’re my own while you’re away. *I have experience working as a dog groomer—I offer bathing services at an additional cost! Feel free to ask.* I currently work remotely full time, so I am available 24 hours a day, 7 days a week to provide attentive care to your dog(s). I have a fenced-in backyard and two friendly Australian Shepherds to keep your dog company. Your dog will have as much supervised outside play time as they would like, and will have free roam of the main floor of my house at other times. If you prefer your pet to be crated at times, just let me know your preference and I’ll be happy to accommodate. ***Note: to avoid stomach upset/any allergic reactions, dogs in my care will ONLY be given food and/or treats supplied and approved by their owner. Additionally, to help protect my family, home and other dogs in my care, I ask that owners please ensure their dogs are up to date with flea/tick/worm preventative. If parasites are found, a $100 cleaning fee will apply.***

Sitter Profile Image: Hannah B.
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Hannah B.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
169 reviews
31 repeat clients
15 years of experience
Culpeper, VA, 22701

I rely on Parker to take care of my boy and she really comes through. I know he looks forward to their visits.

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Linda B.
Sitter Profile Image: Makayla R.
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Makayla R.
from
$25
per walk
5.0 out of 5 stars
20 reviews
5 repeat clients
4 years of experience
Culpeper, VA, 22701

She was great! Came on short notice and Daisy loved her walk.

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Vas G.
Sitter Profile Image: Ronda S.
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Ronda S.
Star Sitter
from
$33
per walk
5.0 out of 5 stars
75 reviews
24 repeat clients
35 years of experience
Culpeper, VA, 22701

Ronda was great and went above and beyond. We needed to book last minute, and she did a meet and greet the same day. Ronda was thorough which put our minds at ease that our baby was well looked after.

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Sasha K.
Sitter Profile Image: Mikayla S.
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Mikayla S.
from
$17
per walk
5.0 out of 5 stars
21 reviews
7 repeat clients
2 years of experience
culpeper, VA, 22701

So far so great!!! Mikayla is a wonderful dog walker and from the time I met her I knew she would be perfect for my boys. Appreciate her support in my doggy care!

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David B.
Sitter Profile Image: Marsha W.
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Marsha W.
from
$25
per walk
5.0 out of 5 stars
17 reviews
6 repeat clients
12 years of experience
Culpeper, VA, 22701

Marsha was terrific- extremely reliable and flexible- and Gigi did great with her!

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Sherri G.
Sitter Profile Image: Megan R.
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Megan R.
from
$24
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Culpeper, VA, 22071

About: As the daughter of a pet-sitting business owner and veterinary technician, I’ve been caring for animals from an early age. With over 10 years of experience working alongside my mother and in veterinary offices across Northern Virginia, I’ve learned that every pet is unique and deserves individualized care. Before moving back to Northern Virginia in 2023, I also owned a successful pet-sitting business in St. Croix, USVI. My own pets have taught me a lot as well—my pit mix, Bella, survived both a fighting-breed environment and Hurricane Maria, and my two rescue bassets struggled with separation anxiety, as well as our Moluccan cockatoo we raised from a nestling. Those experiences reinforced the importance of patience, empathy, and consistency. I’m a non-smoker, organized, and detail-oriented. I’m also available for last-minute needs and those holiday plans that sometimes run longer than expected. Above all, I take this work seriously and will care for your pet with the same love I give my own. 🐾🖤 Working mainly from home allows me the flexibility to plan my days around feeding, walks, playtime, and making sure pets feel safe, loved, and cared for. In my home or a client’s, I follow each pet’s usual routine for feeding, walks, play, and rest, while giving them plenty of love and attention to keep them comfortable. We can work on learning new tricks and reinforcing obedience training.

Sitter Profile Image: Caroline B.
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Caroline B.
from
$18
per walk
5.0 out of 5 stars
1 review
5 years of experience
Culpeper, VA, 22701

About: I’m currently doing a certificate online to become a pet vet assistant,I also like baking in free time and spend time friends ,and I mainly love dogs and cats since growing up I currently don’t have job at the moment and I wanted to get some experience being around pets more often so I’m available most of the time so I thought why try this I care for any pet that I run into even if I don’t know them well,for example on one of my walks I helped a woman catch there dog that got off there leash

Sitter Profile Image: Jocelin B.
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Jocelin B.
from
$25
per walk
5.0 out of 5 stars
38 reviews
19 repeat clients
10 years of experience
Culpeper, VA, 22701

About: I’ve been caring for pets for over 7 years, and it’s something I genuinely love. I have experience with dogs of all sizes from energetic puppies to senior dogs who need extra care and attention. I treat every pet like family and always make sure they feel safe, comfortable, and loved. Pet care is a regular and rewarding part of my weekly routine. I’m calm, dependable, and attentive to each pet’s needs making sure they get the right balance of exercise, playtime, and rest throughout the day. Pets stay in a clean, cozy, and pet-friendly space with plenty of room to relax or play, including a fully fenced yard where they can safely explore and enjoy the outdoors. There’s always someone home even if I need to step out briefly, my mom grandma or my boyfriend, who are both equally experienced and caring with pets, are always around to help. I usually introduce them during meet and greets so everyone feels comfortable and at ease

Sitter Profile Image: Carmen M.
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Carmen M.
from
$15
per walk
5.0 out of 5 stars
4 reviews
11 years of experience
Culpeper, VA, 22701

About: I have been pet sitting and house sitting for 1+ days at a time for about 11 years. I treat every home with respect and all pets as my own. I love bonding with and meeting new animals! Each family I've sat for has called me back to sit for them again! Additionally, I have met many new doggos when babysitting in new family's homes. I always treat the pets just as well as the kiddos, giving them lots of love and behind the ear scratches. My family has always had dogs and I've loved dogs of all breeds since I was a little girl. I am a full time speech-language pathologist during the school year, but have flexibility in my schedule and I’m working from home half of the week. I am available for am/pm/afternoon drop in/walk visits and some weekends depending on location and dates. In your home I am comfortable and confident in my abilities taking your dogs out for walks on leashes, or leaving them out in the backyard to get some movement. I can stay and play for a while as needed to give them attention. I have a loving pit-mix at home. If our dogs got along we could potentially plan on having your pet come stay with us for a week/weekend! Additionally, we do have enough space (2 level home), a crate, and a fenced in yard so we can accommodate having another dog who does not get along with other dogs.

Sitter Profile Image: Cynthia T.
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Cynthia T.
from
$20
per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
21 years of experience
Culpeper, VA, 22701

About: I am owned by my Australian Shepherd mix Luke, Flat Coat Retreiver Mack, chihuahua mix Dover and Jack Russel Dallas and I am here to put your mind at ease while you go on vacation or out of town for a business trip! I also have extensive experience with the feline variety. I am an EMT-B for humans, but I have also taken training classes in dog/cat CPR and Heimlich. Not that we will need it. I have experience in administering medication by mouth, IM injections and testing blood glucose. Feel free to contact me with any questions. I would prefer to stay in your home so that the fur kid will be more comfortable and maybe it will help with any separation anxiety. I do not mind bringing in the mail or any other task that may be similar.

Sitter Profile Image: Ashley S.
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Ashley S.
from
$18
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
4 years of experience
Culpeper, VA, 22701

Ashley came through for us and our dog Nacho extremely last minute. She was awesome at communicating and our dog seemed very happy upon our return home. We will definitely use Ashley again in the future and also recommend her services.

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Melissa M.
Sitter Profile Image: Madison R.
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Madison R.
from
$18
per walk
5.0 out of 5 stars
13 reviews
5 repeat clients
12 years of experience
Culpeper, VA, 22701

About: Dogs have been part of my life for as long as I can remember. I grew up with dogs on a farm, apartment, townhouse, etc. I have experience with many different personalities, energy levels, and breed needs I currently have two dogs of my own, a great pyrenees and a golden retriever. I’ve also worked at a veterinary clinic as a vet tech, gaining additional experiences with animal care, health needs, and proper handling. I beleive no dog should be judged by their breed or put under a general label. I focus on their body language and individual personalities, while still addressing breed needs. I currently am working 32-40 hours a week that gives me a certain level of flexibility to match your schedule. I receive my schedule every Saturday, two weeks posted at a time. I will give full transparency if there are any schedule conflicts. I understand how important it is to feel comfortable leaving your pet in someone else’s care, they’re your family! My goal is to always make sure both you and your pet few safe, supported, and at ease while you’re away. I do my best to follow your pet’s routing exactly the way you do at home, adjusting to whatever care instructions you prefer. I am also more than happy to provide updates as often as you’d life, whether that’s daily or hourly check-ins, photos, or videos so you can see how your pet is doing. I pay close attention to your pet’s behavior, health, and surroundings, making sure they’re safe and comfortable both inside the home and in outdoor spaces. I keep information on local vets and emergency clinics on my phone. I treat every pet and home with the same care and respect I would my own!

Sitter Profile Image: Roland B.
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Roland B.
from
$30
per walk
5.0 out of 5 stars
2 reviews
3 repeat clients
25 years of experience
Culpeper, VA, 22701

Roland's first time with Scrappy. I certainly appreciated his input. Very knowledgeable and helpful. Would highly recommend Roland , for whatever your dog needs...Looking forward to have him walk Scrappy again.

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apollogrizz1
Sitter Profile Image: Lakeshia W.
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Lakeshia W.
from
$18
per walk
5.0 out of 5 stars
29 reviews
9 repeat clients
5 years of experience
Culpeper, VA, 22701

About: I’ve taken care of dogs of every kind since I was 10. Neighbors, friends and family have relied on me to walk, feed and bathe their pets I am not working at the moment so I have a lot of free time. I am a stay at home mom of older boys. I have a friendly Pitbull to keep your fur baby company and a crate in case it is needed for your friendly caring loved animal

Sitter Profile Image: Stephanie S.
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Stephanie S.
from
$30
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
25 years of experience
Culpeper, VA, 22701

Stephanie was great, she came in and walked my big baby and gave him some much needed snuggles. I booked her last minute to help and she saved the day!

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Rebecca K.
Sitter Profile Image: Kenzie B.
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Kenzie B.
from
$20
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Culpeper, VA, 22701

About: I have 7 years experience as a veterinary technician and many more just in general. I have a bachelor’s degree in pre-veterinary biology along with many animal internship experiences. Along with my children, we can give your pets attention and lots of love! If your pet does not like children we can also establish another plan of care. I am also able to keep small and exotic animals. Please only reach out if you are a serious inquiry. Please know that I make my plans around watching and taking care of your fur babies so that I can give them all the love and attention I possibly can while you are away! I have a giant fenced in yard and a very friendly dogs. I am able to come to your house for potty breaks and feedings. I do require proof of up to date vaccines (bordatella, rabies and distemper.) Must also have an up to date NEGATIVE fecal and heartworm test and your pet must be up to date on flea and tick medication.

Sitter Profile Image: Billy C.
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Billy C.
from
$16
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Culpeper, VA, 22701

About: I love animals. I will take the best care of your pet. I'm fine with handling aggressive ones and bigger dogs too. I've taken care of animals all my life, so you can travel without a worry. Right now I'm open any day and time. I can overnight stay and house sit as well. I'm a fan of cats and other animals too. I'll follow your instructions to the letter. I will always call for questions and not assume something on your property. I'm fine with taking videos and pictures

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

Dog parents share their Rover experiences - Winfrey

1 / 1
5.0 out of 5 stars

Katie has been absolutely amazing with Cas, he’s a bit of a tough cookie requiring lots of patience due to him being older and partially deaf/blind. Me being chronically ill and working with long commutes, Katie has been a lifesaver and accommodated last minute requests! Highly recommend.

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Aspen C.
Dog Walking
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How Rover works

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Sitters in Winfrey average 3
repeat dog walking clients

FAQs for Dog Walking - Winfrey

Frequently asked questions about Rover

The average cost for Dog Walking in Winfrey on Rover is $16.65 per walk (as of June 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .

As of June 2026, there are 987 sitters on Rover offering Dog Walking across Winfrey. 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 Winfrey. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winfrey.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

Yes, you can find walkers who have experience with handling special pet needs in Winfrey. On Rover:

  • 92% of walkers can help with special care needs
  • 97% can help with giving oral medications or injections
  • 94% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.

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