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

Over 8 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.

About: I’ve had dogs and cats of all shapes and sizes my entire life, and caring for animals has always been a huge part of who I am. Over the years I’ve owned and cared for many different breeds and personalities, including Saint Bernards, Great Danes, and Coonhounds, which gave me plenty of experience handling large and giant-breed dogs. I’ve also shared my home with multiple cats over the years—many of them seniors—so I understand the patience, routine, and gentle care older pets often need. I’ve spent years fostering animals as well, frequently working with senior pets and dogs that may be anxious or slow to trust new people. I pride myself on being patient and letting animals warm up to me at their own pace so they can feel comfortable and safe while their owners are away. My home currently includes an Alaskan Klee Kai and a Border Collie mix, so daily life already revolves around exercise, enrichment, and making sure dogs stay happy and engaged. When I travel, my trips are often pet-focused—I’ve driven cross-country multiple times with my dogs to explore new trails, parks, and adventures together. For walks, drop-ins, and house sitting, I always aim to keep pets on their normal routine so they feel secure in their own home. As a larger and experienced handler, I’m comfortable managing multiple dogs on leash and adapting to different energy levels—whether your dog loves long walks and playtime or prefers relaxed companionship and a calm presence. I’m also experienced in administering most medications and providing attentive care for senior pets who may need a little extra support. I have a very flexible work schedule, and can accommodate most dogs needs! I no longer offer overnight sitting, but can accommodate multiple drop ins and walks while you are gone, start long as early as 7 am and as late as 8-9 ish. Your dog’s comfort and routine are my top priorities. I provide focused attention, interactive play, and companionship tailored to your pup’s personality — from calm evenings at home to energetic walks or adventures at parks and trails. I’m experienced with all sizes and breeds, so whether your dog is a tiny pup or a gentle giant, they’ll receive care that’s attentive and consistent. My goal is for your dog to feel safe, happy, and fully engaged throughout their stay
About: My family & I been around & cared for kitties & puppies for 20+ years. I’ve personally owned chickens & rehabbed bunnies & squirrels. My fur family is extremely important to us & we pledge to care for your pets like our own. We have a fenced in backyard and plenty of domestic pet care experience. Currently I’m a full time homemaker and have lots of time to spend quality time with your fur babies. Occasionally my husband Brandon helps with Rover duties. He is awesome with both animals & people! If needed I have the ability to separate my pets & yours. I can administer medicine including injections with proper instructions. Ask me about brining in mail, watering plants, garden care, farm animal care, & light cleaning. Call my Rover number to receive my personal cell phone Having extra puppies around the home is easy & we can offer long potty breaks in our fenced in backyard as well as a daily walk! The home & yard are secure & your fur babies will be safe with us. Please let us know if your pup tends to run/escape!
About: I've been caring for dogs and cats in a personal and professional capacity for 25 years now. For many years, I turned our home into an orphan kitten and cat rescue and worked with the organization Planned Pethood to care for and adopt out over 50 cats! I've taken care of cats and dogs for friends, family, and clients in all life stages - from bottle babies to elderly and incontinent cancer patients. I have experience administering pills and insulin injections, and welcome working with dogs and cats at all life stages. Tricky diets and particularities don't put me off.. I've seen it all! Long walks and cuddles are my specialty, and I look forward to making new four legged friends! I'm currently completing a graphic design certificate online, so my schedule is incredibly flexible. I'm available both weekdays and weekends, as I have no particular set schedule. I make sure to keep dogs on their leash during walks, and to secure all yard gates before letting them outdoors. I keep the home clean and tidy, and make sure there haven't been any accidents or breakages. I tend to stay at the home all day when staying overnight so the animals always have company and any emergencies are handled immediately.
About: I've owned pets my whole life. My gentle composure and empathic nature make them feel loved and safe with me. I fostered a puppy from the Caribbean that nobody else wants to deal with. Within a month, she let me pet her and take her on walks. I train dogs with care and lots of pets! I am a freelancer and work from home. Dogs that stay at my house can go in and out and be protected by a fenced-in yard. I will ask about diet, routines, and special needs for your pets. I will come to your house for free for a meet and greet and see if we connect with your pet.
About: Before joining Rover I mainly provided my services through word of mouth. I have experience with providing basic medical care for dogs and cats, and training experience including potty training and easing separation anxiety. I have vast experience and knowledge on various breeds and their specific needs, and really just love being able to have the time and availability to be able to provide these services. They say a dog is a man’s best friend, but in my case, a dog has always been a woman’s best friend! I offer dog sitting, walking, training and boarding at my home as well. I am brand new to the app but I do have plenty of references and want to make all owners feel just as comfortable as I want to ensure their pets will feel with me! I currently work a part-time job from my home, so I have a flexible schedule and able to meet any needs your pet has. I am available everyday, all hours mainly, and can accommodate you and your pets schedule! In my home all pets are welcome. I have plenty of walking trails and a back yard for pets that stay at my home. I typically will customize the walks, food, bathing etc depending on the needs of the pet and what works best for them and the owner.
About: I have been passionately caring for dogs, cats, and horses since high school, building years of hands-on experience with animals of all kinds. I worked professionally as a dog walker and pet sitter for an Annapolis-based pet care company, providing reliable services to pet owners throughout Annapolis and Arnold. While attending college full time, I also worked as a barn assistant at a large horse boarding facility in Sandy Spring, where I gained extensive experience in daily horse care and stable management. After moving to Stevensville, I continued working as a barn assistant for two horse farms caring for multiple horses. My lifelong love for animals, combined with my professional experience, allows me to provide attentive, compassionate, and dependable care for both household pets and horses. I’m currently working part time locally where I work 8 hour shifts a few days a week. I will work closely with you to ensure your pet’s routine works smoothly with mine. Your pet’s safety, comfort, and well-being are always my top priorities. I strive to create a calm, trustworthy, and stress-free environment where pets feel secure, loved, and cared for as if they were my own. I am attentive to each pet’s individual needs, carefully follow owner instructions, and maintain a clean, safe environment during every visit, walk, or overnight stay.
About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.
About: As a dedicated dog walker and in-home pet sitter with over two years of experience, I know how important it is to find someone you can truly trust with your pet. I care for every dog (and cat!) as if they were my own — with patience, love, and attention to their unique needs and routines. What You Can Expect: ✅ Safe, fun, and tailored walks ✅ Home visits that follow your pet’s schedule ✅ Clean water, food, meds (if needed), and lots of affection ✅ Daily photo updates and messages so you never have to wonder how things are going ✅ Respect for your home and your pet’s space I’m trained in basic pet first aid and always check collars, leashes, and gates before heading out. Whether it’s a quiet walk or an energy-burning play session, your pet's safety and happiness are always my top priority. Let’s schedule a meet-and-greet! I’d love to learn more about your pet and how I can help make your time away stress-free for both of you. 🐶🐾 Pet care fits naturally into my daily routine because of how flexible and rewarding it is. Since I set my own schedule, I can book pet care clients around my part-time job shifts and study blocks, which helps me stay balanced and productive. Walking dogs gives me a much-needed mental reset from screen time and studying, and it keeps me active throughout the day. It’s also a great way to supplement my income without taking on another traditional job. Most of all, spending time with animals brings me a lot of joy and motivation — it breaks up long study days and reminds me why I love what I do Whether you’re at work or away for a few days, I provide reliable, in-home care that keeps your pets safe, happy, and stress-free in their familiar environment. From daily walks to feeding, playtime, and medication routines, I tailor every visit to your pet’s unique needs. 🔐 Safety & Professionalism Equipped for pet first aid always carrying a kit Detailed home-entry and security protocols Leash and harness checks before every walk Weather-conscious and always alert to potential hazards Respectful of your home, your pets, and your time 📸 Peace of Mind After each visit, you’ll receive a photo and short update so you know how your furry friend is doing — because trust is built on communication
About: What sets me apart from other sitters is trustworthiness, reliability, punctuality, and care. I care for others' animals just as I would my own! With love, attention, and energy. I’m typically available from Thursdays - Sundays. Please reach out to confirm 24 hours in advance so I can make sure my schedule aligns with yours. I can adhere to any guidelines you set for me while in your home. I am a trustworthy and respectful sitter who will take loving care of your furry family members like they're my own!

About: I’ve been caring for dogs of all sizes and personalities since I was young. I grew up with dogs in my home and currently have two dogs of my own, so I know how much our pets mean to us and how important it is to find someone you can trust with them. I love getting to know each pet’s unique personality and making sure they feel safe, comfortable, and loved while their owners are away. I truly love all fur babies and would be so excited to care for yours! 🐾❤️ I am currently a part time student at Anne Arundel community college. I also have a part time job. My weekends are available. Weekdays I have a lot of free time during the day between classes before I head to work at 2:30-5:30 (usual hours). Safety is my top priority when caring for your pets. I will always make sure they are supervised, secure, and comfortable, whether we are out on a walk, during a drop-in visit, or staying overnight. I follow each pet’s routine and any instructions you provide, including feeding schedules, medications, walks, and anything else that helps them feel at home.
About: I’ve grown up around dogs, from friends to family, and have a family diva shih tzu in Maryland that is mostly family trained. I’ve also fostered a pitbull mix for a month! I’m also a dog walking volunteer at a local animal shelter. I’m good with animals and as an eldest sister I have a natural caretaking instinct (as well as being responsible and hard working ) :) I currently am a Ballet Dancer with the St Louis Ballet and have a part time job. That being said most of my morning and nights are available for all your pups / kitties needs :) I am an avid walk talking and will indulge in a run if your pet is up to it! I make sure to follow the owners instructions and treat the pet as it was my own, as well as the owners property and belongings
About: I have a one year golden retriever who I raised on my own since he was 8 weeks. I’ve also have experience pet sitting, walking family and friends animals throughout the years I’m currently working full-time on the weekdays and attending AACC gnursing school starting in August . However I have open availability to watch your fur babies all through out the weekend! I have a friendly golden retriever boy to keep your fur babies occupied. I’ll be home majority of the day to keep them comfortable and safe.
About: Hi everyone! I’m a vet tech by day and have been in for about 7 years. I love all fur babies and would love to meet your babies. I’m currently working at a veterinary radiation clinic in Annapolis. I have worked at an Emergency Room for animals in Columbia. I do work from 8am to 1pm but am sometime off early. I will take care of your babies as if they were my own. I understand that our fur babies mean a lot to us and that they are family.
About: Dogs have always been part of our family, and I have over 15 years of hands-on experience caring for dogs of all ages, sizes, and personalities. As a family with three friendly dogs, we understand how important it is to know your pet is safe, comfortable, and loved while you're away. We provide a clean, structured, and supervised home where dogs receive plenty of attention, playtime, exercise, potty breaks, and affection throughout the day. We are experienced with puppies, senior dogs, administering oral medications, maintaining feeding schedules, crate-trained dogs, and multi-dog households. Every dog is treated like one of our own. You'll receive regular photo and video updates so you can relax knowing your pet is happy and well cared for. Our goal is to create an stress-free, loving environment where every dog feels at home. My family and I have a flexible schedule that allows us to provide consistent care and supervision throughout the day. Because we work from home part of the week, there is almost always someone available to monitor, play with, and care for your dog. We maintain regular feeding schedules, frequent potty breaks, daily exercise, enrichment activities, and plenty of affection. We offer flexible drop-off and pick-up times whenever possible and work hard to accommodate each family's needs. Your dog's safety, comfort, and happiness are our top priorities. We have a clean, smoke-free home with a dedicated space designed specifically for boarding dogs, giving them plenty of room to relax, play, and feel comfortable. We have three friendly, well-socialized dogs and always introduce pets carefully to ensure everyone gets along. We closely supervise all interactions and can separate dogs whenever needed for meals, rest, or individual care. We follow each owner's feeding schedule, medication instructions, exercise routine, and any special requests. We welcome crate-trained dogs and can accommodate dogs who need extra attention, senior care, or a quieter environment. You'll also receive daily photo and video updates so you can enjoy peace of mind while you're away.
“Heather was Great!!! She was always on schedule and communicated well. She was very attentive and understanding when my pup had a stomach bug while we were on vacation. I would 100% recommend Heather to anyone looking for a caring dog sitter.”

About: I am a reliable pet care provider with a deep love for dogs and animals. With extensive experience caring for dogs of all sizes, from teacups to giants and from high-energy puppies to gentle seniors. I ensure that each pet receives personalized attention. Whether I am walking your dog or staying in your cozy home to care for your furry friend, I strive to create a welcoming environment where your loved one feels at ease. My flexibility in scheduling and willingness to provide outside playtime and walks will provide ample opportunities for your pet to enjoy exercise. I am also experienced at caring for senior and special needs animals, including sight and hearing-impaired dogs as well as animals needing medicines administered on a regular basis. I am a strong believer in being very responsive through the Rover App, providing regular updates, immediate answers to any questions you may have, and of course pictures of your furry friend! I look forward to becoming a cherished part of your pet's life! Working from home allows us to be available around the clock, ensuring your pets receive constant attention and care at any time they may need it. We ensure constant supervision for pets in both our home and yours, never leaving them unattended and always treating them with the same care as if they were our own.
The median cost per walk for dog walking in Chester 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.
How to book dog walking

1. Search
Browse profiles of walkers near you who offer dog walking.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog walking - Chester
Select a filter and find qualifying sitters offering dog walking.Sitters in Chester average 4 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 October 2026. Most bookings cost between $22 and $23 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 October 2026, there are 4,900 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:
- 87% of walkers can help with special care needs
- 92% can help with giving oral medications or injections
- 95% 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.



