Dog Walking Chester

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Over 64
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
20 reviews
6 repeat clients
20 years of experience
Chester, VA, 23831

Reagan and Brody enjoy Amanda!

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Beverly W.
Sitter Profile Image: Phyllis N.
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Phyllis N.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
99 reviews
43 repeat clients
50 years of experience
North Chesterfield, VA, 23237

Absolutely amazing experience. Work and day to day has been made so much more enjoyable and I have so much appreciation for the patience my pup is experiencing. I will be a regular for quite some time. Thank you again Phyllis!

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Megan B.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
49 reviews
10 repeat clients
15 years of experience
Chester, VA, 23831

Sabrina did an excellent job of gaining the trust of my dogs! They enjoyed the walks very much.

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Lecia J.
Sitter Profile Image: Lindsey R.
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Lindsey R.
from
$18
per walk
5.0 out of 5 stars
9 reviews
4 repeat clients
2 years of experience
Chester, VA, 23831

About: I love dogs, they are my favorite people. All shapes and sizes, whenever I spend time with them, they just make my heart happy. When they’re with me they’ll be taken good care of. Whether it’s long walks, games of tug of war, endless belly rubs, and lots of cuddles. I will love your pet as if they were my own. In addition to raising two dogs of my own, I’ve cared for friends and neighbors’ pets while they’re at work or away. I know how hard it is to leave your pet behind whether it’s while you’re at work or on vacation but when they’re with me you won’t have to worry because they’ll be well cared for and loved. I work full time Monday through Friday from 8am-5pm but only live 5 minutes from my work. I am able to go home midday and have evening and weekends free to spend lots of time with your fur babies. I make sure that they will remain on they’re regular feedings and pawty schedules and are free to run the apartment if no need to crate. My apartment provides a fenced in yard for them to have safe and fun outdoor time. I work full time Monday through Friday from 8am-5pm. I am able to have evening and weekends free to spend lots of time with your fur babies. I will make sure that they will remain on they’re regular feedings and pawty schedules and are free to run the house if no need to crate. My house provides a fenced in yard for them to have safe and fun outdoor time.

Sitter Profile Image: Tiffany B.
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Tiffany B.
from
$25
per walk
5.0 out of 5 stars
28 reviews
12 repeat clients
23 years of experience
Chester, VA, 23831

Tiffany is amazing! She goes above and beyond. This is truly her passion. She loves what she do and it shows. This is my third time using Rover and she is the best one we booked for our Buddy. Tiffany, I hope you are available whenever me and my family decides to travel.

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Nancy W.
Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$16
per walk
5.0 out of 5 stars
2 reviews
3 years of experience
Chester, VA, 23831

About: I specialize in dogs that need a little extra grace and a lot of patience, but I also love a social butterfly! Having raised a reactive high-drive mix and managed the pulling power of large breeds like Labs and Great Danes, I know firsthand that not every dog is an easy walker. I bring a calm, highly disciplined, and observant approach to every visit, ensuring your dog feels secure and understood. ​My Special Skills Include: ​Reactive & Anxious Dog Handling: Creating safe, low-stress environments for sensitive souls. ​High-Drive Breed Management: Experience safely handling and exercising powerful, high-energy working breeds. ​Behavioral Reinforcement: Utilizing consistent treat training, professional handling techniques, and keen observation of canine body language. ​Large Breed Experience: Confident leash-handling for strong pullers. ​Whether your dog is a socialite who loves making friends or a sensitive pup who needs a sitter with unshakeable patience, I tailor my approach specifically to them. Pet care is a staple of my daily routine! While I work a standard 9-to-6 business day 5 days of the week, I am wide awake and ready to go for those early 5:00 AM or 6:00 AM morning walks. Your pup will get plenty of exercise and attention before I head out, and I’m back in the evenings for more play, dinner, and potty breaks until 10:00 PM. I specialize in recurring schedule drop ins and walks, ensuring your pets have a consistent best friend to look forward to constantly. Whether I’m staying at your place or visiting for a drop-in, your pets are treated like family. My approach combines physical exercise with mental engagement—I love incorporating short, positive training sessions into our day to keep their minds sharp. They’ll get plenty of 'tummy rub' downtime and scheduled feedings, but they’ll also get the structure and play they need to stay happy and tired out. Your dog won't just be watched; they’ll be active, engaged, and thoroughly spoiled.

Sitter Profile Image: Sarah K.
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Sarah K.
from
$20
per walk
5.0 out of 5 stars
7 reviews
2 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: Rangeen A.
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Rangeen A.
Star Sitter
from
$20
per walk
4.9 out of 5 stars
37 reviews
10 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: Cassidy R.
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Cassidy R.
from
$15
per walk
5.0 out of 5 stars
30 reviews
12 repeat clients
25 years of experience
Chester, VA, 23831

About: I’ve taken care of dogs/cats for friends and family for as long as I could remember. I am always looking for ways to play with dogs and other animals, because who doesn’t want unconditional love and affection from fur babies. I’ve volunteered with animal shelters for three years whether that be playing with the dogs up for adoption or taking them out for a fun day with lots of walks and attention! I’m currently available anytime during the week or weekends to care for your animals whenever they need some additional love whether that’s for just a quick potty break or a nice long walk! Taking care of your pets in your home means always respecting the rules you have in place to ensure consistency is a daily and followed routine. I will treat every pet as if they were my own with love and care as I know they are essential in your home.

Sitter Profile Image: Darnell M.
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Darnell M.
from
$18
per walk
5.0 out of 5 stars
101 reviews
38 repeat clients
14 years of experience
Colonial Heights, VA, 23834

Darnell is incredible! Our dog loves to see him each day. He is very sweet and makes me feel better when I’m at work knowing my pup is ok at home. Thank you so much!!!

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Brittany M.
Sitter Profile Image: Jeanette A.
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Jeanette A.
from
$25
per walk
5.0 out of 5 stars
11 reviews
1 repeat client
30 years of experience
Chester, VA, 23831

About: For 30 plus years I had my own dogs from Rottweilers to peekapoos. Always had two so they had a buddy. Well trained where I didn’t need a leash. I babysit my friends dogs here at the house. I’m auntie. They go home spoiled. I travel a lot so, when my dog passed away I did not get another one. I work from home. I am empty nester who just went through a divorce. They can hangout with me all day. Ability to leave on the weekend to come back as required. Full fenced in yard. Traditional metal fence. With only two neighbors who have no animals. Quite neighborhood with a place to walk them around ponds.

Sitter Profile Image: Hailey S.
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Hailey S.
from
$14
per walk
5.0 out of 5 stars
3 reviews
15 years of experience
Chester, VA, 23831

About: I’ve had all types of breeds and sizes growing up! From german shepherds, to goldens, to mixed breeds from the shelter. I’ve learned their tricks and how to cater to each personality! I’m an Army officer looking to fill her time with furry friends! I’m always available after 1800 everyday (I’m at work from 0530-1700) and weekends of all times are free! I treat every home with respect and cleanliness as I enter/move about/exit! It’s important that the dog/cat feels safe in their own home as I care for them in whatever way!

Sitter Profile Image: Lisa C.
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Lisa C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
70 reviews
21 repeat clients
40 years of experience
North chesterfield, VA, 23237

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

Crystal was so accommodating and great with our 2 dogs while I was away. She provided me with updates and made being away from my babies a lot less stressful. We will definitely be booking with her again! Thank you for everything, Crystal!

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Jasmin V.
Sitter Profile Image: Karen T.
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Karen T.
from
$25
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
16 years of experience
North Chesterfield, VA, 23234

About: Hi! I’m a lover of all pets, young, old, big, and small! I have one dog, a 12-year-old Chesapeake retriever mix, and a 2-year-old Great Pyrenees mix. I am an experienced dog lover who you can trust to take fantastic care of your pup! Apart from taking care of your pups, I believe in good customer service; all instructions you leave me will be followed with the utmost care to keep them wagging! So when can I start? I am in school, and therefore my availability is flexible! Please reach out to me if you have any questions or need certain times for your loves! I have a townhome with two dogs and prefer to take care of your pups at your home where they feel comfortable the most! 😃

Sitter Profile Image: Alecia B.
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Alecia B.
Star Sitter
from
$13
per walk
5.0 out of 5 stars
58 reviews
20 repeat clients
20 years of experience
Chester, VA, 23836

I selected Alicia to help us with Karmas walks during my hip replacement surgery recovery. She and Karma became fast friends immediateky. Eighteen walks later it was sad to say goodbye. Alicia is very kind, prompt, flexible and trustworthy just to make a few. We are blessed to have been able to have her help us!

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Debbie S.
Sitter Profile Image: Allejah K.
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Allejah K.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
6 reviews
7 repeat clients
14 years of experience
SOUTH CHESTERFIELD, VA, 23834

Allejah was great . Ciroc really enjoyed her . She kept me updated and I felt safe leaving my dog with her. I would highly recommend!

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Janayla W.
Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
209 reviews
59 repeat clients
10 years of experience
Chester, VA, 23831

Thank you so much for taking care of our dogs again and for doing it on such short notice! It’s so nice having someone so reliable and trustworthy. I know they’re already looking forward to your next visit!

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Jasmin V.
Sitter Profile Image: Melissa M.
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Melissa M.
from
$25
per walk
5.0 out of 5 stars
1 review
1 repeat client
30 years of experience
Chester, VA, 23831

About: I've cared and been around pets and dogs of all breeds all my life. My family has always had dogs so I have experience feeding, grooming, playing, walking, administering simple medication, and basic training. I'm a mom of 7 that works part-time, with little ones in school, so I have the means, time, professionalism, and drive to play and care for your four legged family member, when your unavailable to.... And your able to rest assure that they are well taken care of :) When caring for pets I am able to visit and care for them in their natural setting.... Of their home, so they more natural and relaxed. Please reach out if your interested in weekend boarding at my home.

Sitter Profile Image: Sarah I.
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Sarah I.
from
$25
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
7 years of experience
Chesterfield, VA, 23832

About: I've been dog sitting since covid; things have changed but not the love for animals. Since my start I've dog sat for a wide varity of dogs. Puppies, oldies, big, small. Some requiring a lot of attention to help distract them, some that just sit by the door waiting for their pawrents to come home. From medications to special diets, specific schedules and give attention if you have the extra time. I will treat your dog as my own! Something you can count on is they will be loved and well taken care of. Pet care is my top priority. Making sure they are fed on time and they get plenty of play time and walks while you are gone. I do currently work but my schedule is constantly changing so I have a lot of freedom to change it as needed. I unfortunately can't accept pets into my home as I don't currently live alone. But I'm more than willing to stay over whenever you need me to.

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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

Phyllis is amazing with my girl Piper. I never have to worry about Piper when she is in Phyllis' care. I highly recommend Phyllis to help with all your fur babies.

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Samantha F.
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
5.0 out of 5 stars

Meghan is punctual, flexible and a great communicator! I love that she's very respectful of my wishes and directions and seems to remember and follows every one of them! We appreciate Meghans help!!!

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Anja D.
Dog Walking
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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 for Dog Walking in Chester on Rover is $22.2 per walk (as of July 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 July 2026, there are 2,349 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 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 Chester.

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 Chester. On Rover:

  • 94% of walkers can help with special care needs
  • 98% can help with giving oral medications or injections
  • 99% 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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