Dog Walking Chester

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Over 77
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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
• 41 reviews
16 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: Sarah K.
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Sarah K.
from
$20
per walk
5.0 out of 5 stars
• 8 reviews
3 repeat clients
15 years of experience
Chester, VA, 23836

About: I promise you trust, communication, comfortability, and great care! I love pets! I grew up with a Golden Retriever named Skippy! I now own my beautiful mut mix of Lab, Pit and Blood Hound. His name is Maverick! He's 2 and such a loving, happy dude! I currently dog sit my mom's 3 Boston Terriors whenever she needs to go out of town and have been since I was a teenager. I also take in my best friend's older pit bull, Cookie, and her and Maverick get along wonderfully! There's plenty of space to walk dogs around my apartment community, along with a fenced in tennis court area where they can run free! I work full time AT HOME so I'm flexible just looking to make some extra money I work from home Monday through Friday, and am available most weekends, so I have lots of time and flexibility to care for your doggos! I live in an apartment but it's very dog friendly! I will ensure your dog gets lots of attention and love! I have access to lots of trails, open pet areas, and a fenced in tennis court where they can run free and we can play fetch! My dog is very friendly and has lots of experience around other dogs. I do have a large dog crate if that is required or necessary.

Sitter Profile Image: Airlea e.
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Airlea e.
from
$15
per walk
5.0 out of 5 stars
• 5 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: Michelle H.
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Michelle H.
from
$25
per walk
5.0 out of 5 stars
• 13 reviews
7 repeat clients
25 years of experience
Chester, VA, 23831

About: I have a lot of knowledge with most exotics as well, I’m happy to help with any bird, turtles/tortoise, fish, snake, any lizard, monkeys, any rodent, rabbit, chicken, horses, pigs, cow, goats and sheep. I’ve taken care of animals my entire life. I also work with The Wildlife Center and do some small animal rehabilitation. I currently have 2 dogs and one fish. I’ve recently fostered 3 tortoises, a senior dog and a bearded dragon. I am able to do some puppy training and very knowledgeable in senior care for dogs and cats. I am currently a stay at home mom and my kids are in school full time. I have my real estate license as well as degree in pharmacology but I’d much rather work with animals at my own pace. I have a decent sized fully fenced in backyard. I am also able to crate your animals if that is something that is preferred. My dogs are extremely sweet and love to play with all of their dog friends that come to visit. They are up to date on all vaccines and my house is very clean but pet friendly. My couch is big enough for all the pups and people here.

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
• 310 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
• 45 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
• 25 reviews
12 repeat clients
30 years of experience
Chesterfield, VA, 23832

“Got along very well with my mini poodle, she may be his new best friend 🧡 they did great together from the moment they meet at the meet and greet, she did an awesome job”

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Cristina C.
Sitter Profile Image: Nadra W.
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Nadra W.
from
$21
per walk
5.0 out of 5 stars
• 7 reviews
2 repeat clients
12 years of experience
Chester, VA, 23836

“Thank for being available last minute.”

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Patrícia Z.
Sitter Profile Image: Shannon O.
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Shannon O.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
• 65 reviews
29 repeat clients
20 years of experience
Richmond, VA, 23234

“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: Elizabeth J.
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Elizabeth J.
from
$20
per walk
25 years of experience
North Chesterfield, VA, 23234

About: My boy kitty passed away last year at 14 years old. He became very sick in his last 2 years so his care required daily shots, weekly vet visits. I became very proficient in giving pills by mouth as well. He was big and strong and didn’t like the vet or car rides so i learned how to best manage a very scared kitty. My mom had a senior dog who developed diabetes so I cared for him in my home for the last few years of his life. I gave him insulin shots twice a day and performed his medical care. I gave him meds by mouth and performed other care duties. I work part-time and am in school at ODU online so my hours are flexible. I live in the Richmond area and service a fairly wide range as I have my own reliable transportation. I prefer to pet-sit in the clients home as I have a cat myself. My grandma rescued hunting dogs, particularly hounds and beagles, when I was growing up, so I am safety minded when it comes to pets, especially ones who get scared easily.

Sitter Profile Image: Steph & Calvin Z.
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Steph & Calvin Z.
from
$25
per walk
4.7 out of 5 stars
• 14 reviews
3 repeat clients
20 years of experience
Chesterfield, VA, 23832

“Thanks so much for taking such great care of Nala!”

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Hannah L.
Sitter Profile Image: Tara W.
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Tara W.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
• 60 reviews
9 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: Michelle C.
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Michelle C.
from
$25
per walk
5.0 out of 5 stars
• 14 reviews
1 repeat client
10 years of experience
Midlothian, VA, 23832

About: I have been taking care of my own dogs since I was young and love to be around all animals! I used to nanny for a family with 5 kids and they had a wonderful dog that I always helped to care for! Feeding and taking him to the groomers and vet appointments…all things that I was lucky to get to help with! I also used to care for 2 cats (both needing to take medication) and a bull dog on a daily basis! I have a Jack Russell (that just passed away) myself that I had for about 10+ years and no kids do she was my only fur baby! I have recently in the past year gotten a brand new puppy named Sugar! She is a beagle/terrier/lab mix and 25 pounds of Adorableness! She is so sweet And absolutely my little girl, as she follows me everywhere and tries to be wherever I am, and always under foot!!! She’s a little skittish and still all puppy at eight months! So I am no stranger to puppy needs at all! I also have Bella, who is a pit/beagle mix and she is a little over a year and a half old! She is 60 pounds of crazy but happy and smart and always at my husband side! What a love bug! But remember, with pets, there is no personal space! Lol I love pets of all kinds and will care for them as if they were my own! Snuggles are free!!! 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: Divine M.
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Divine M.
from
$16
per walk
5.0 out of 5 stars
• 3 reviews
2 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: Danielle A.
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Danielle A.
from
$25
per walk
5.0 out of 5 stars
• 35 reviews
12 repeat clients
20 years of experience
Hopewell, VA, 23860

“Prompt and communicates in a timely manner. Very polite and very attentive to my fur baby’s needs.”

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Matthew N.
Sitter Profile Image: Joanette C.
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Joanette C.
from
$35
per walk
4.9 out of 5 stars
• 42 reviews
18 repeat clients
9 years of experience
A chesterfield, VA, 23834

“Jo is fantastic with our dogs. Astrid, our most reserved dog rolled over and showed her belly. My wife was also able to meet her and also loves her. She played with our pups and once she left, they were exhausted and napped. A tired dog is a good dog!”

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Kerry-Ann P.
Sitter Profile Image: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
• 335 reviews
92 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: 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

Sitter Profile Image: Jordyn C.
Verified Enhanced Background Check
Jordyn C.
from
$20
per walk
15 years of experience
Petersburg, VA, 23803

About: Lifelong experience caring for dogs of various breeds, sizes, and temperaments, including feeding, walking, administering basic care, monitoring behavior, and providing a safe, attentive, and comfortable environment for pets. I am currently going to college and have too much time on my hands. What better time to spend my free time than with your pups. Safety, trust, and creating a positive environment are my top priorities when caring for pets. Having been around dogs my entire life, I understand the importance of patience, consistency, and attentive care. I always ensure pets are supervised, comfortable, and treated like family while maintaining a clean, secure, and stress-free environment. I believe strong communication, reliability, and genuine compassion help build trust with both pets and their owners, allowing every dog to feel safe, happy, and cared for while in my care.

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

Dog parents share their Rover experiences - Chester

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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

Phyllis is simply awesome. Apollo loves her. She takes him on fairly long walks. It is very helpful for his mid-day break!

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Kevin 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 on Rover is $22 per walk as of October 2026. Most bookings cost between $17 and $24 per walk. 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 October 2026, there are 2,343 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 your 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 , 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 , 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 .

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
  • 95% 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 .

walkers on Rover set their own , 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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