Dog Walking Chester

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Over 78
pet parents in Chester have booked dog walking

Chester, 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: Amanda B.
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Amanda B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 46 reviews
19 repeat clients
20 years of experience
Chester, VA, 23831

“Holly cannot wait until she for the days Amanda comes. She loves her “fren”!”

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Kimberly B.
Sitter Profile Image: Meghan T.
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Meghan T.
from
$22
per walk
5.0 out of 5 stars
• 17 reviews
5 repeat clients
20 years of experience
Chester, VA, 23831

“Meghan was very reliable, trustworthy, and provided excellent care for my dog. She gave us updates and pictures with every walk. We felt very confident knowing Roman was in good hands. She was very flexible and was able to acommodate our last minute changes. We're so lucky to have found you and would love to continue booking with you in the future ❤️”

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Cindy C.
Sitter Profile Image: Airlea e.
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Airlea e.
from
$15
per walk
5.0 out of 5 stars
• 6 reviews
13 years of experience
Richmond, VA, 23237

About: I have over a decade of professional pet care experience as well as a lifetime of personal pet care experience. I prefer to work with the elderly or medically complex pets as I know they need special attention, adherence to routines, and a calm environment. I focus on providing fun daycare and boarding for pets that don’t do well in regular boarding facilities and require a more home-like experience. Prices are negotiable after a meet and greet. Please fill out your profile in full before meeting! Incomplete/no profile image profiles will not be given my address. I work from home so I spend a majority of my day with my pets and guest pets. Dogs are given mostly free range inside and allowed outside into the huge fenced yard many times a day. They get playtime with other pets and alone time when needed. Our yard is fenced and our house is doggy proofed to avoid trash cans, toilets, and non-chewable items from being accessed. Dogs are crated when they can’t be supervised.

Sitter Profile Image: Melanie K.
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Melanie K.
Star Sitter
from
$21
per walk
5.0 out of 5 stars
• 47 reviews
6 repeat clients
10 years of experience
Chester, VA, 23831

“Melanie was excellent with my big happy dog! She is very reliable and communicative and I highly recommend her services!”

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Molly R.
Sitter Profile Image: Morgan W.
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Morgan W.
from
$25
per walk
5.0 out of 5 stars
• 6 reviews
1 repeat client
9 years of experience
Chester, VA, 23831

About: I have previously worked in a kennel at an animal hospital for 3 years, years of house sitting services along with pet care provided on Rover. I have had cats and dogs of my own (pitbull mix and beagle mix). My schedule is flexible to be able to provide pet care services. I'm available for mid-day walks or drop-in visits during 11-2 Monday through Friday. I do not offer pet care services in my home but can ensure to cultivate safety, trust, and respect while offering services in your home.

Sitter Profile Image: Crystal C.
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Crystal C.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
• 314 reviews
109 repeat clients
15 years of experience
South Chesterfield, VA, 23834

“Thank you for taking Eileen for a walk. I know it was very hot and I appreciate the care you took with her!! The break in a long day while I’m at work helps.”

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Mars L.
Sitter Profile Image: Rangeen A.
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Rangeen A.
from
$30
per walk
4.9 out of 5 stars
• 46 reviews
14 repeat clients
10 years of experience
Richmond, VA, 23237

About: I am a former dog owner who's trained a few dogs. I will treat the dog like my own! I understand the importance of routine, exercise, and cuddles! I work full time. Mostly from home. My significant other has an alternative schedule so the dog would be under 24 hour supervision. I can't wait to have a buddy with me throughout the day! I understand how anxious your paw partner may be while you are away -- I am here to console your paw partner until you are back 💕 I live in a single home with a large fenced backyard with a pool they can play in! Great parks and trails nearby. Dogs will have freedom in all rooms of the home. Dog will be supervised 20-24 hours a day. This helps me ensure pet safety and quick turnaround on any changes to health and/or behaviors.

Sitter Profile Image: Jynette V.
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Jynette V.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
• 32 reviews
15 repeat clients
30 years of experience
Chesterfield, VA, 23832

“My border collie hates to be left alone. When I got home after Jynette’s visit, Keira was calm and happy. So the visit and potty break were just what she needed. Great job!”

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Susan K.
Sitter Profile Image: Madison G.
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Madison G.
from
$16
per walk
4 years of experience
Chesterfield, VA, 23838

About: I’ve taken care of dogs since i was about 14 for family and neighbors around. Growing up i’ve had dogs from pit bulls, german shepherds to chihuahuas, so i’m familiar and comfortable with all kinds! As a full-time online college student, I have a flexible schedule that allows me to dedicate plenty of time to pet care throughout the week. Since I complete my classes online, I can easily plan my day around pets needs. I am responsible, organized, and able to provide feeding, walks, playtime, and lots of love. I always make sure pets feel safe, comfortable, and loved while in my care. I follow feeding schedules, provide fresh water, keep their environment clean, and make sure they get plenty of attention and exercise. I also follow the owner’s instructions carefully and provide updates so they can feel comfortable knowing their pets are in good hands.

Sitter Profile Image: Shannon O.
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Shannon O.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
• 66 reviews
29 repeat clients
20 years of experience
Chesterfield, VA, 23832

“Lovely young lady, friendly and professional. Walked my 2 girls for a few days while i was recovering from surgery - they were happy and excited to see Shannon and enjoyed their walks!”

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Lee P.
Sitter Profile Image: Tara W.
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Tara W.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
• 64 reviews
10 repeat clients
10 years of experience
Chesterfield, VA, 23832

“Tara responded immediately to a last minute request to walk my dog two days later so that I could be away for a day. Everything went very well!”

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Jennifer W.
Sitter Profile Image: Divine M.
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Divine M.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
3 repeat clients
4 years of experience
Richmond, VA, 23231

“Divine takes such good care of our Winnie! She’s the first dog walker we’ve hired and she has been flexible with our schedule changes week to week, sends the sweetest pictures, and is always on time.”

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Kali N.
Sitter Profile Image: Hana J.
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Hana J.
from
$25
per walk
5.0 out of 5 stars
• 20 reviews
5 repeat clients
17 years of experience
Colonial Heights, VA, 23834

About: I’ve owned and cared for furry (scaled and feathered!) friends my whole life. From cats and dogs, to guinea pigs and bunnies, to fish and birds. I even have experience caring for sugar gliders and a ball python. I’ve worked as a pet uber (with a company called Leash) and volunteered at shelters, socializing events, and cat rescues for several years, so I’m used to interacting with all kinds of pet personalities and ages. From shy snugglers, to loyal guardians, to spunky characters, to goofy adventurers, I love them all! You can trust I will love on your baby and treat them with as much care as I do my own fur babies. My schedule is fairly flexible right now since my medical retirement from the Army in October. I’m currently working on an online M.S. in psych and substitute teaching in my boyfriend’s town (Clarksville, VA) whenever I’m available. Since it’s a long commute and I’m typically called the morning of, I try to keep Monday and Tuesday open to sub if needed. I am more than willing to do virtual and in person meet and greets to learn pet needs and routines. I prefer to meet in person to get acquainted with your pet while they feel safe in your presence (but I’ve never met a pet I didn’t click with and love immediately.) I’ll accept any additional written/typed outlines detailing your pets care if that’s easier than leaving notes in the app. You name it and I’ll do it; whatever is best for you and your fur baby. Dogs under my care will enjoy long walks and dog parks trips where applicable. If you have a puppy (or dog) in training, I love to partner in their learning using whatever commands you prefer. Kitties under my care will get lots of playtime with wands and lasers, as well as tons of snuggles.

Sitter Profile Image: Michelle C.
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Michelle C.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 18 reviews
3 repeat clients
15 years of experience
Midlothian, VA, 23832

About: Hey everyone! I’m a dedicated pet caregiver who treats every animal as if they were my own fur baby. I’ve been sitting on Rover for 4 years (18 five-star reviews!), and bringing happiness to pets and peace of mind to their parents is what I do best! What You Can Always Expect From Me:: • ❤️ Family-Level Love: Extra cuddles, attentive routine care, and tons of love for dogs, cats, and multi-pet households of all sizes! • 🏠 Above-and-Beyond House Sitting: Total respect for your home. You’ll return to a clean, well-kept space and happy pets. • 📸 Lots of Updates: Regular photos and transparent communication so you never miss a beat. • 🗓️ Reliable Routine: I’m available Tue/Wed/Thu/Sat/Sun all day, and Mon/Fri for morning/evening care and overnight house sits (around a fixed daytime shift). Rover keeps everything safe and protected, so you can sit back and relax on your trip. I can’t wait to pamper your pets! 🎉 I am currently a part-time private nanny, to a bunch of different families who may need care for their little ones day a week, and my schedule is always changing from week to week so my availability will always be changing. But,I will try to keep my Rover calendar up-to-date as I hope more of you reach out! The plan is is turn this into a full-time gig so I will have probably more availability as time goes on towards the end of this year, but I’m hoping to find some regular clients that will book with me on a consistent basis! Plus, I’m really looking forward to all the pet snuggles! I am always very mindful of the time for feedings and walks…any medication will be given correctly and timely…I will make sure your home is locked up after I leave from a walk and/or feeding! Please know that I will do my best to. Gain the trust of the animal! Cats too! I do highly recommend a meet & greet ahead of time so we can meet pet parents and also meet dog(s)! Let’s them see me and hopefully remember me and feel comfortable with me in their house! (*Please note: House Sitting rates apply to stays where overnight accommodations (a clean bed/space) are provided in your home. If you prefer daytime/evening visits only without overnight stays, please book via my Drop-In rates!)

Sitter Profile Image: Kayce M.
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Kayce M.
from
$25
per walk
4.9 out of 5 stars
• 156 reviews
32 repeat clients
15 years of experience
Petersburg, VA, 23803

“Kayce is wonderful with Rio and I can tell he looks forward to seeing her. She keeps me posted of his activities and is on top of all his well being. Thank you always!”

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nathalie m.
Sitter Profile Image: Julia H.
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Julia H.
Star Sitter
from
$28
per walk
5.0 out of 5 stars
• 57 reviews
20 repeat clients
16 years of experience
North Chesterfield, VA, 23236

“Julia did an amazing job keeping my puppy busy while I was in a meeting. She is very reliable and I would definitely book again. I loved seeing the pictures and that she included a write-up of all the fun things they did together.”

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Erin D.
Sitter Profile Image: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
• 339 reviews
94 repeat clients
30 years of experience
North Chesterfield, VA, 23236

“Damacia is great with our giant Schnoodle. He loves squirrels but she manages to control him. We have used her for boarding and walking and always been pleased. I would highly recommend.”

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Cindy M.
Sitter Profile Image: Danielle A.
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Danielle A.
from
$25
per walk
5.0 out of 5 stars
• 37 reviews
12 repeat clients
20 years of experience
Hopewell, VA, 23860

“I know when my dog is in Danielle's care, I am super comfortable. I find her reliable, flexible with her schedule, and her to be caring and a trusting person.”

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david m.
Sitter Profile Image: LaMia S.
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LaMia S.
from
$15
per walk
10 years of experience
Henrico, VA, 23231

About: I have had all sorts of animals throughout my life. I’ve never worked with dogs professionally but I’ve had multiple family dogs ranging from Chihuahuas to Pit bulls and I loved and cared for all of them. I currently have 2 Pit bulls that are loved and happy. I also often help pet sit in the neighborhood. During the school year I will be in class from 8 to 3 but after that I have plenty of time to walk and/or care for your pet. I have no other priorities so taking care of your fur baby will be my main focus. I am typically well liked by dogs and I am patient with dogs that are still in training so if needed I can go at your dogs pace making them more comfortable.

Sitter Profile Image: Daeshard b.
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Daeshard b.
from
$23
per walk
5.0 out of 5 stars
• 3 reviews
13 years of experience
Petersburg, VA, 23803

About: With 13+ years of dedicated experience caring for dogs and cats, I specialize in providing safe, structured, and deeply compassionate care. From training energetic puppies to managing medical needs for senior pets, I treat every animal like family As a disabled veteran with a lot of time for pet care. I bring discipline, structure, and calm patience to managing your dog or cat’s routine, medication, and unique needs. I treat the client's home with the utmost respect, maintaining cleanliness, following security protocols and keeping a low profile. Special needs and senior aniamls are not a problem

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

Dog parents share their Rover experiences - Chester

1 / 1
5.0 out of 5 stars

Sarah has been walking my dog one day a week for for a few months. I know my dog is in great hands. She communicates is flexible with our schedule. Definitely recommend!

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david m.
Dog Walking
5.0 out of 5 stars

Phyllis does an amazing job! You can't go wrong using her services, you can tell she genuinely cares about our pets.

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Todd R.
Dog Walking
5.0 out of 5 stars

Maryuith was able to take Roman out on a last-minute walk today, and she did a wonderful job. She was very communicative and sent us photo updates. She even made sure he had water without us having to ask. We are definitely looking forward to having Maryuith care for Roman again in the future!

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Cindy C.
Dog Walking
5.0 out of 5 stars

Amanda was great with our active dog. This was our first experience with Amanda and she went above and beyond with Sadie.

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James M.
Dog Walking
5.0 out of 5 stars

Melanie was excellent with my big happy dog! She is very reliable and communicative and I highly recommend her services!

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Molly R.
Dog Walking
5.0 out of 5 stars

Lisa is a friendly and thoughtful dog walker that arrives on time, replenishes water bowls if needed and provides the attention, walks and treats Tut is looking forward to when he’s home for the day! Will book again

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Christine H.
Dog Walking
5.0 out of 5 stars

Abby walked my golden doodle, Ainsley, Christmas Day. What a relief it was to know a lovely reliable person like Abby was coming over to take care of Ainsley. I would recommend her with enthusiasm.

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Milissa G.
Dog Walking
5.0 out of 5 stars

Sabrina is a great dog walker and Karma loves her. Sabrina got me out of a last minute jam this morning. Thank you!!!!

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Debbie S.
Dog Walking
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How to book dog walking

  1. 1. Search

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Popular requests for dog walking - Chester

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Sitters in Chester average 3
repeat dog walking clients

FAQs for Dog Walking - Chester

Frequently asked questions about Rover

The average cost of Dog Walking in Chester is $22 per walk as of November 2026. Most bookings cost between $17 and $24 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 2,362 sitters on Rover offering Dog Walking across Chester. 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 Chester. 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 Chester 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 Chester. On Rover:

  • 91% of walkers can help with special care needs
  • 94% can help with giving oral medications or injections
  • 96% 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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