Dog Walking Wintergreen

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

End
Search

Wintergreen, 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.

1 / 1
Sitter Profile Image: Kathryn B.
Verified Enhanced Background Check
Kathryn B.
from
$15
per walk
10 years of experience
Afton, VA, 22920

About: I’ve had pets my whole life. I love dogs and cats. I love animals and have no problem spending my free time taking care of and playing with some fur babies. I have a pug that I've had since she was 6 weeks old. I also have a cat who I took in after his old owner abandoned him. I currently work full time Monday-Friday 8-5pm in Charlottesville. I am more than happy to stop by after work if needed or if you want me to stay at your place I can take care of the babies before heading to work to make sure they are fed and worked. Can work with a lot of schedules. I do make and sell jewelry so there may be a few weekend days where my availability is limited due to already committed to a craft show In my house I try and take my dog out every 2 hours. In the summer my pug is sensitive to heat so we do short walks around our driveway. She is a bit spoiled and will not go outside in the rain so I do also have experience cleaning up puppy pads and encouraging their use. My cat is both indoors and outdoors so he goes to the bathroom outside but also have a litter box inside I clean every few days for him.

Sitter Profile Image: Tyler C.
Verified Enhanced Background Check
Tyler C.
from
$10
per walk
4.9 out of 5 stars
20 reviews
5 repeat clients
28 years of experience
Roseland, VA, 22967

Great communication and wonderful with my Caddie. A big help for me while visiting Wintergreen for the weekend. I will certainly ask Tyler to help again when I return.

Profile image
Dave K.
Sitter Profile Image: Shay M.
Verified Enhanced Background Check
Shay M.
from
$25
per walk
22 years of experience
Afton, VA, 22920

About: I grew up with dogs, cats, goats, chickens, pigs, peacocks. You name it. I’ve been a huge fan of animals since I can remember. I’m super active outside and love taking pups out on hikes or walks. My last dog had to take meds so I’m also extra sensitive to pups that may need more present care. I’ve dog sat and house sat for many years before and just recently decided to give rover a try. I’m also a photographer so pics of your sweet pea will be guaranteed! I’m a photographer so my schedule varies. Sometimes I’m on a shoot or at home editing. I work part time at a restaurant wed-Friday so am unavailable those evenings. I am generous with my love with pets if they want that. If they are shy I will absolutely listen to what they need and let them warm up to me at their own pace. I am clean and respectful of others’ space and strive to make sure your sweet pup gets the activities they deserve.

Sitter Profile Image: Zeigh Z.
Verified Enhanced Background Check
Zeigh Z.
from
$20
per walk
5.0 out of 5 stars
7 reviews
9 repeat clients
12 years of experience
Waynesboro, VA, 22980

Zeigh has been extremely prompt and reliable in walking our dog 3x per week. Our dog has some special needs and she has been patient and accommodating to building a relationship with him. Thank you!

Profile image
Jade K.
Sitter Profile Image: Kristina A.
Verified Enhanced Background Check
Kristina A.
from
$30
per walk
5.0 out of 5 stars
5 reviews
25 years of experience
Lyndhurst, VA, 22952

About: I have been a dog and cat owner/lover/advocate my whole life. I miss having my own pets so much so I pet sit during our travels and while we are home too! I’m a massage therapist and energy worker so animals LOVE my touch and calming presence. I’m very active and love long walks. I’m totally comfortable with large dogs. I have retired early so my schedule is very flexible. I am happy to travel to pet sits. I tend to do pet sitting in Florida during the months of January and February. I love having dogs and cats in my home. There is a little river behind my house and the national forest and Sherando Lake Recreation Area is just beyond the river so there’s lots of space for long walks. Pets will get lots of loving care, tons of cuddles, and undivided attention while under my care and I will walk for as long and far as your dog (or cat) wants to.

Sitter Profile Image: Ashley C.
Verified Enhanced Background Check
Ashley C.
from
$45
per walk
11 repeat clients
24 years of experience
Stuarts Draft, VA, 24477

About: Hello, I am excited to meet you and your pup. I have worked professionally in clinic and in behavior for the last 21 years. I am a positive reinforcement based trainer for Good Pup. I have 3 personal fur babies and I foster with Save Rocky The Great Dane Rescue. I am currently working part time time so I have time in my schedule to devote to your fur kids. I have a doggie door for the emergency potties and I enjoy training so that can be part of the routine. I have a fenced in yard and I am able to provide mental enrichment as well as physical walks/Sniffari adventures and I have personal pups to keeps your busy! I have the ability to crate and even do drop bys at your house if needed.

Sitter Profile Image: Jackie B.
Verified Enhanced Background Check
Jackie B.
from
$25
per walk
5.0 out of 5 stars
10 reviews
1 repeat client
50 years of experience
Afton, VA, 22920

About: I’ve owned and have taking care of pets for years. Would love to help folks out now that I’m retired. Reliable, dependable and own property and near trails. Retired and happiest around animals. Love walking, hiking and being outside. My home is clean and pet friendly. I have trails nearby and live on 2 acres I have 2 acres and trails. Or happy to give care in your home walking, visiting or staying over. I’m healthy and active and ready!

Sitter Profile Image: Taylor M.
Verified Enhanced Background Check
Taylor M.
from
$20
per walk
5.0 out of 5 stars
1 review
5 years of experience
Roseland, VA, 22967

So glad Taylor was able to help us last minute! Exactly what we needed and looked like Bentley has a good walk :)

Profile image
Candice K.
Sitter Profile Image: Michael M.
Verified Enhanced Background Check
Michael M.
from
$20
per walk
4.9 out of 5 stars
38 reviews
20 repeat clients
15 years of experience
Waynesboro, VA, 22980

Michael was a breeze to schedule with, very flexible and considerate!! Mickey had a great time and was well cared for, would definitely recommend!

Profile image
Brennan D.
Sitter Profile Image: Angel B.
Verified Enhanced Background Check
Angel B.
from
$15
per walk
5.0 out of 5 stars
49 reviews
17 repeat clients
6 years of experience
Greenville, VA, 22989

Angel is GREAT! She is very kind and is great with my pup!

Profile image
Courtney K.
Sitter Profile Image: Emma B.
Verified Enhanced Background Check
Emma B.
from
$18
per walk
5.0 out of 5 stars
1 review
1 repeat client
13 years of experience
Afton, VA, 22920

About: I have had pets from day one. My family has had 4 cats, 2 dogs, hamsters, lizards, fish, and even a hedgehog!. I’m currently a Nursing student who’s past career was a veterinary technician. Caring for animals is my passion and I hope I get to meet your fur babies sometime and give them some extra love. I have experience with dogs with special needs as well as dogs who are in rehabilitation. I am up for any task that includes a precious pup or any other fur baby that needs me. I look forward to meeting you and you’re families and hopefully be honored to care for your lovely pets! I have a flexible schedule and am very accommodating. If there is a will there is a way is how I think of things, you can always count on me! Unfortunately at this time I do not do in home boarding as I have my own little circus of fur babies who are friendly but just don’t like change.

Sitter Profile Image: Reese M.
Verified Background Check
Reese M.
from
$30
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
11 years of experience
Afton, VA, 22920

About: In a home with lizards, fish, a cat, a dog, and a flock of chickens, I spend my days tending to the heard. Animals all with their own unique personalities and each requiring different levels of care. Feeding, Bathing, Grooming, Spoiling with TLC, I do it all! I am a new mom and spend my days at home so I have a lot of free time to pop over and care for animals as needed At my house the dog and cat are indoor/outdoor pets who come and go when the please, as the door is usually wide open! Because of this I usually opt. to care for pets in the comfort of their own homes and abide by the routines they are adapt to.

Sitter Profile Image: Faith H.
Verified Enhanced Background Check
Faith H.
from
$15
per walk
6 years of experience
Waynesboro, VA, 22980

About: Hi! I’m a stay-at-home mom and lifelong dog lover who has been around dogs my entire life. While I’m new to Rover, caring for animals has always been a part of my home and family life. I currently have a dog of my own and understand how important it is to find someone trustworthy and loving to care for your pet. Our home is full of love, play, and attention. I have young children who have been raised around animals and are gentle, respectful, and enjoy helping give pets extra affection (with supervision, of course!). Your dog will be treated like part of the family while they’re here. Whether your pup loves to play, relax, go for walks, or simply be near people, I’ll do my best to make them feel comfortable and at home. I’m happy to follow feeding schedules, medication routines, and any special instructions to help keep your dog’s routine consistent. I know how much pets mean to their families, and my goal is to provide a safe, caring, family-oriented environment where both you and your dog can feel at ease. I look forward to meeting you and your furry friend! 🐾❤️ Im currently a stay at home mom that’s trying to make some extra cash. Im flexible and can work with most schedules to ensure your pup gets the care they deserve. As a dog owner myself, I know pets are family. I’ll care for your dog as if they were my own, ensuring they receive plenty of attention, affection, and supervision in a safe home setting. If I am watching your furry friend at your home you can expect me to be professional, courteous, and respectful of your property.

Sitter Profile Image: Meredith B.
Verified Enhanced Background Check
Meredith B.
from
$25
per walk
4.5 out of 5 stars
18 reviews
9 repeat clients
2 years of experience
Waynesboro, VA, 22980

About: I’ve taken care of all kinds of pets over the years. Neighbors, family, and friends have relied on me to feed, walk, and bathe their pets. I’m currently working part-time, so I will have plenty of time to play with your pups! I’m available for boarding Wednesday, Thursday, and Friday after 11am. I live in a small neighborhood with places to go for walks and have lots of backyard space. Perfect for playing fetch with your pups!

Sitter Profile Image: Natalie A.
Verified Background Check
Natalie A.
from
$20
per walk
15 years of experience
Stuarts Draft, VA, 24477

About: I have extensive experience caring for a wide variety of animals. Animals are one of the most important things in my life and I know how important they are to their families. Pets are like kids and traditional boarding is never the first choice. Keeping your pet in it’s home where it is most comfortable and knowing it is getting the best care possible provides peace of mind, something money can’t buy. My goal is always to provide that peace of mind for a pets family while they are gone. Whether it is boarding, or having frequent around the clock care at your home for your pet, a simple personalized walk or check in during the day, we would do anything for our pets, and that is what I’m here for. I treat each and every animal as if it’s my own and know communication is the most important and keeping in touch and updates, even when not required, are always appreciated by a pets owner. I strive to become a familiar face for each pet so they are as happy and comfortable as possible and so each owner has a reliable and trustworthy source for any needs they may have for their pet. I work from home with my own schedule so I am extremely flexible in accommodating your pets needs and last minute requests to make your life easier! I take care of your pets like they are my own! I have pretty much done it all, and am happy to do it. I am very particular about who cared for my pets when I am away, and will treat yours with nothing less than I would expect for my own. I want them to be as comfortable as possible like you’re not even gone! Familiarity, comfortability, for pets and their owners is key.

Sitter Profile Image: Nicolette K.
Verified Enhanced Background Check
Nicolette K.
from
$15
per walk
25 years of experience
Charlottesville, VA, 22903

About: I have a passion and connection to animals. I’ve always worked with them and have had them as pets for as long as I can remember. Weekends are when I am most available but also a lot of holidays and afternoons. Even some more mornings. It just depends on the day. I treat my pets like they are my children. I would do the same with anyone else’s. There’s nothing more innocent then animals and kids.

Sitter Profile Image: Casey Y.
Verified Enhanced Background Check
Casey Y.
from
$25
per walk
15 years of experience
Waynesboro, VA, 22980

About: I absolutely love animals and have had them through out my entire life. I have experience from working at “Dogtopia” to “Home away from home, dog boarding”. I understand the importance of family and would love to be your dogs next best friend! I have experience providing care for a variety of animals, including feeding, grooming, and monitoring health. I am familiar with cleaning and sanitizing animal housing and equipment, and can recognize signs of illness or distress. By feeding, walks, and playtime—with my personal habits like breakfast, exercise, and evening relaxation it helps to create a consistent, healthy routine. My successful routine with my 12 year old senior terrier includes early morning engagement to set a positive tone, scheduled midday breaks or mental stimulation to combat boredom, and structured evening bonding that eases stress. I have a 12 year old friendly Emotional support animal named Flower, who still loves to run and play. I also live close to the park, and have a crate if needed.

Sitter Profile Image: Nadine E.
Verified Enhanced Background Check
Nadine E.
from
$18
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
15 years of experience
Fishersville, VA, 22939

Nadine is great with our pup Jack, easy to work with and super dependable!

Profile image
Trish F.
Sitter Profile Image: Aurora R.
Verified Enhanced Background Check
Aurora R.
from
$45
per walk
4.9 out of 5 stars
13 reviews
7 repeat clients
10 years of experience
Waynesboro, VA, 22980

Aurora is amazing and will definitely be our #1 go to person for additional pet care. Our pup absolutely loved Aurora. She was very communicative with us throughout the day while we were away, which was awesome since this was our first experience using a service like this.

Profile image
Daniel R.
Sitter Profile Image: Emily P.
Verified Enhanced Background Check
Emily P.
from
$22
per walk
5.0 out of 5 stars
189 reviews
75 repeat clients
8 years of experience
Waynesboro, VA, 22980

Reliable, sweet, great with our dog!

Profile image
Stephanie H.
1 / 1
View more sitters

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

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

Meet local walkers who will treat your dogs like family

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Wintergreen average 3
repeat dog walking clients

FAQs for Dog Walking - Wintergreen

Frequently asked questions about Rover

As of July 2026, there are 757 sitters on Rover offering Dog Walking across Wintergreen. 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 Wintergreen. 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 Wintergreen.

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 Wintergreen. On Rover:

  • 98% of walkers can help with special care needs
  • 100% 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 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge