Dog Walkers in Chestertown, MD

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

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Top rated Chestertown dog walkers

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: Sabrina G.
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Sabrina G.
from
$25
per walk
4.6 out of 5 stars
32 reviews
9 repeat clients
15 years of experience
Chestertown, MD, 21620

Sabrina is always interacting with Peaches and has bri get her dogs to teach Peaches how to play.

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Jane Ann W.
Sitter Profile Image: Elaine P.
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Elaine P.
from
$20
per walk
5.0 out of 5 stars
17 reviews
6 repeat clients
20 years of experience
Chestertown, MD, 21620

About: I grew up on a farm in Eastern Washington, around many different animals. My whole childhood was waking up early, to feed and care for all the animals. I have fostered 18 dogs until they found furever homes. I have experience in dealing with special needs animals to include, horses, cats, dogs, cows, chickens and goats. I have lots of experience in dealing with with dogs who have a more aggressive personality as I have fostered many and they needed time to adjust to new environments. I currently have two dogs and a cat. I would love to spend time and care for other animals while you’re away!! With being a stay at home parent I have a pretty flexible schedule. I go to the gym mon-fri 9-11 but am free before and after. My 3 year old goes to daycare Tuesday and Thursday. I can accommodate for her to go elsewhere if you prefer to not have a child in the home I completely understand it! If not, she is very respectful and kind to animals. I will follow whatever instructions are provided to me. I understand wanting your pets taken care of exactly how you want them to be and what makes the pets most comfortable. I am currently not accepting for pets to be in my home as I have an elderly dog who doesn’t do well with that set up.

Sitter Profile Image: Alia R.
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Alia R.
from
$20
per walk
2 years of experience
Petworth, Chestertown, MD, 21620

About: What sets me apart is that I’m a total cat lover my whole life. I’ve had four cats so far in my life, so I’m super comfortable around them and really understand their wants and needs. I’m a college student home for the summer, and I genuinely love helping people with their pets. I’m responsible, caring, and always make sure animals feel safe and loved while their humans are away. Pet care fits really well into my routine! I work as a hostess a few times a week, so I have a pretty flexible schedule with plenty of time to give pets the attention and care they need. Whether it’s feeding, playing, or just hanging out and keeping them company, I love making them feel happy and comfortable!!! When caring for pets in a client’s home, I always try to keep their routine as normal and comfortable as possible. I make sure they have fresh food and water, clean up after them, and spend quality time playing, cuddling, or just keeping them company. Whatever they’re used to and enjoy! I’m respectful of the home and always make sure things are clean and tidy before I leave. My goal is to make both the pet and the owner feel at ease while they’re apart.

Sitter Profile Image: Madison K.
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Madison K.
from
$10
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Worton, MD, 21678

About: I have grown up with having dogs as pets my whole life. I grew up on a farm so I have experience in caring for livestock as well. I have a very flexible schedule this summer including weekdays and weekends as I am home from college for summer break. Please feel free to reach out! I have been around many types of dogs so I have experience with all types. Based on what the owner wants to be done/ the dogs needs I’m happy to help.

Sitter Profile Image: Gillian H.
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Gillian H.
from
$15
per walk
1 repeat client
14 years of experience
Chestertown, MD, 21620

About: I have loved animals since I was a little girl! I have many years of experience with dogs, cats and even small animals like hamsters, turtles and fish. I want to be there for you, and your furbaby so you can fully relax on that vacation you have been looking forward too! I am currently employee at Washington College with a pretty loose schedule! Being able to choose my hours and be able to work around yours is 100% a possibility that sets me apart! I live in an apartment with a fenced in backyard. I live in downtown chestertown which is open to all different types of walking opportunities and is a short walk to many fields at the college!

Sitter Profile Image: Ashley C.
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Ashley C.
from
$25
per walk
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Centreville, MD, 21617

I appreciated her flexibility and text/picture updates

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Meaghan K.
Sitter Profile Image: Beverly H.
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Beverly H.
from
$25
per walk
5.0 out of 5 stars
11 reviews
1 repeat client
10 years of experience
Church hill, MD, 21623

Beverly was awesome. We needed someone on short notice and she stepped right in for us. She met the dogs the night before and today she kept us updated on both the walks. Highly recommend her services.

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MIchael C.
Sitter Profile Image: maranda c.
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maranda c.
from
$20
per walk
5.0 out of 5 stars
12 reviews
2 repeat clients
10 years of experience
Church Hill, MD, 21623

Great communication before and during booking

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Meaghan K.
Sitter Profile Image: Andrew G.
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Andrew G.
from
$18
per walk
15 years of experience
Church Hill, MD, 21623

About: I’ve spent the last 15 years caring for animals and treating every pet like part of the family. I have hands-on experience with 3 cats, a lovable Frenchie Pug, and plenty of experience handling different pet personalities, routines, and energy levels. From daily walks and feeding schedules to playtime and cuddles, I make sure every pet feels safe, comfortable, and cared for while their owners are away. As a pet owner myself, I understand how important it is to have someone trustworthy and dependable caring for your pets. I focus on creating a calm, loving environment while keeping routines consistent so pets feel at ease. Whether your pet is energetic, shy, playful, or needs extra patience, I’m committed to giving them personalized care and attention every step of the way. I take care of my animals everyday I walk them and feed them and they use the restroom in our fenced in yard I give them lots of love as well I have a fenced in yard and 5 friendly animals 3 cats and 2 dogs who are docile and very friendly to any pet that comes in to my home

Sitter Profile Image: Cynthia R.
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Cynthia R.
from
$45
per walk
30 years of experience
Rock Hall, MD, 21661

About: I have been born and raised to take care of any type of family member from the small lizard to largest dog to feathered friends and horses. I love all animals and I have family members of my own. Plus I have a little helper who isn't scared of anything and loves to help her momma as much as she can. I'm will to do what ever it takes to make sure everyone is a happy camper and provide the best care I can to keep your mind at ease knowing you family is in good hands. Feel free to ask me anything and if you have any special requests let me know I will do what I can to make it happen. I'll treat your kids as if they were my own. I'm currently employed part-time but I'm looking to get out of the retail business and starting my own pet sitting business where I can enjoy doing what I love. I currently live in a small apartment, so it ideal that I travel back and forth from my house to clients home. I have fur babies and a family of my own, hopefully when I get a home of my own I could introduce the doggy daycare and pet sitting at my home.

Sitter Profile Image: Sabrina M.
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Sabrina M.
from
$48
per walk
4.9 out of 5 stars
14 reviews
1 repeat client
24 years of experience
Millington, MD, 21651

Sabrina was fantastic to work with. Prior to booking her, she came over and met our dog and my wife and I to ensure that we were all a good fit. She talked with us for a good amount of time, and when she left my wife and I were already very comfortable with her. She walked our puppy exactly when she said she would, gave us an update on how she was doing, and was just amazing to work with. We can’t recommend her highly enough.

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Will W.
Sitter Profile Image: Carolyn G.
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Carolyn G.
from
$25
per walk
5.0 out of 5 stars
1 review
45 years of experience
Galena, MD, 21635

About: I’ve had several dogs through out my life. I’m an animal lover. I’ve had Shetland sheepdogs and I currently have 3 English Bulldogs in my home. I have a very flexible schedule. I’m available to do multiple drop in visits throughout the day and night. I have weekday and weekend availability I do not offer pet care in my home. I am able to come to your home to care for your animals. Client home care only

Sitter Profile Image: Jennifer S.
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Jennifer S.
from
$40
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
4 years of experience
Centreville, MD, 21617

About: As a CPDT-KA certified trainer, I offer dog walking services that go beyond basic exercise. Each walk incorporates training and enrichment tailored to your dog’s unique needs. My expertise is ideal for dogs who are fearful, nervous, hyper, or reactive—especially those other walkers may find challenging. A training walk is a perfect way to advance your dog’s progress when your schedule is too packed for regular training sessions. Please note: My walking services are not suitable for aggressive dogs. If you’re dealing with aggression, please contact me directly or explore my specialized training services. I offer training walk services Monday through Friday, with both daytime and evening availability. For the best results, I recommend scheduling two sessions per week, such as Monday/Tuesday or Wednesday/Thursday. I exclusively use positive reinforcement techniques to care for and train dogs, whether during training walks or in your home. My focus is on creating a safe, encouraging environment that builds trust and confidence in your dog. Each session is tailored to meet your dog’s unique needs while reinforcing good behaviors in a kind and effective way. With this approach, I ensure your dog feels supported and thrives in their routine.

Sitter Profile Image: Aliciya M.
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Aliciya M.
from
$20
per walk
15 years of experience
Queenstown, MD, 21658

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.

Sitter Profile Image: Rylee L.
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Rylee L.
from
$10
per walk
8 years of experience
Earleville, MD, 21919

About: As a dedicated pet caregiver, I have hands-on experience caring for dogs of all ages, breeds, and energy levels. I currently care for my own three dogs—a 5-year-old Rottweiler, Koda, a 1-year-old Shepherd/Pit mix, Gus, and an 8-year-old English Bulldog, Daisy—each with their own unique needs and personalities. From high-energy walks to gentle care for senior dogs, I’m well-versed in providing attentive, reliable, and loving support. I manage daily routines including feeding, bathroom breaks, and exercise, and I understand the importance of consistency and patience in pet care. My experience makes me confident in handling a wide range of canine behaviors and ensuring pets feel safe and comfortable while you’re away. Pet care fits naturally into my routine, as I’m passionate about caring for animals outside of my full-time job. I work weekdays from 8 AM to 3 PM, which allows me to be available for evening visits during the week and fully available on weekends. This schedule gives me the flexibility to provide consistent, attentive care—whether it’s for evening walks, feeding, or full-day care on Saturdays and Sundays. Whether caring for pets in my home or a client’s, I focus on creating a safe, comfortable, and low-stress environment. In my home, pets are treated like family—with plenty of affection, structured routines, and supervised play. I ensure regular feeding, bathroom breaks, and exercise, tailored to each pet’s needs. In a client’s home, I respectfully follow their established routines to help pets feel secure in their familiar surroundings. I’m attentive to each animal’s behavior and comfort, and I’m always focused on providing consistent, reliable care.

Sitter Profile Image: Crystal D.
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Crystal D.
from
$15
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
17 years of experience
Ridgely, MD, 21660

About: I am a dedicated and compassionate individual with a deep understanding of the physical and emotional needs of animals. I currently own two dogs of my own. A huge goldendoodle and a tiny yorkie, so I know how to handle many sizes of animals. I’m also currently working as a kennel tech at a business near by. Vim experienced in feeding. Administering medication and monitoring animal health, always prioritizing their wellbeing and comfort. I treat each animal I meet with the respect and love they deserve. Please feel free to message me with any questions. I hope I get the chance to meet you and your fury bestie/ besties soon My availability is always open. I will not have other commitments other than your fur baby/babies. Once booking they are my priority. I also I make sure I have lots of communication if wanted/needed when your dogs with me! As I would be coming to your home, I will do exactly as told, by you the owner. My main priority is your animals health and well-being.

Sitter Profile Image: Gabriela W.
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Gabriela W.
from
$18
per walk
8 years of experience
Townsend, DE, 19734

About: Although my family has never owned a dog, I have always loved taking care of my aunts, neighbors, and family friends dogs. I always make sure to pay attention to detail when watching a dog and meet each dogs needs whether that be a walk, playing with a toy, belly rubs, or even just relaxing. As a part-time graduate student at USM, I will have time during the day for a dog walk, or to check-in on your pup! I will be available on most weekends for house and dog sitting. I am available to come to your dog and stay with him/her so they do not have to move out of their comfortable environment and stay at a new space with new people.

Sitter Profile Image: Busara C.
Verified Enhanced Background Check
Busara C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
76 reviews
9 repeat clients
5 years of experience
Dover, DE, 19904

About: As a devoted pet mother to two wonderful dogs and a playful cat, I understand the deep bond we share with our furry family members. My journey in animal care goes beyond my own pets; I have always had a passion for understanding and prioritizing the well-being of animals. From a young age, I was fascinated by veterinary care, which led me to pursue opportunities within the veterinary field. Over the years, I have gained invaluable experience that has equipped me with the skills to provide top-notch care for pets of all kinds. My background has taught me not only the basics of pet health and safety but also how to recognize subtle signs of stress or discomfort in animals. I take pride in creating a caring and nurturing environment for your pets, ensuring they feel comfortable and loved while you're away. My goal is to treat your pets as if they were my own, providing them with the attention and affection they deserve. You can have peace of mind knowing that your beloved companions are in capable hands, allowing you to focus on your day without worry. Choosing me as your dog sitter means you're opting for someone who truly cares about the well-being of your pets. I’m dedicated to making your life easier and your pets' experiences enjoyable. Let’s work together to ensure that your furry friends receive the best care possible! I am always available whenever I can be of service ! Never ever a big change to my day I am a mother of pets your furry friends will find a safe and welcoming environment designed for their enjoyment and comfort. Whether it’s fetching a ball or just enjoying the fresh air, they’ll have plenty time to have a blast!

Sitter Profile Image: Brianne S.
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Brianne S.
from
$20
per walk
4.0 out of 5 stars
4 reviews
1 repeat client
15 years of experience
Chester, MD, 21619

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.

Sitter Profile Image: Gabby J.
Verified Background Check
Gabby J.
from
$25
per walk
9 years of experience
warwick, MD, 21912

About: I will take care of your pets as I would my own. I currently have three rabbits and a cat of my own. Over the years, I have provided pet sitting services for many clients, primarily caring for dogs. You can reach out to me at any time during the period that I am looking after your pets. This is my side job, I am a professional photographer as well but if I get a request I will accept to the first of my availability! Is my house equipped with a large mansion for my rabbits, where they are free to roam. As of your home i will go as your home rules are.

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Over 29
pet parents in Chestertown have booked dog walking

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

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Sitters in Chestertown average 3
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Chestertown on Rover as of May 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Chestertown dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of May 2026, there are 641 dog walkers in Chestertown. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 88% of Chestertown dog walkers respond in under an hour.

Dog walkers in Chestertown have an average of 15 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Chestertown.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 641 dog walkers in Chestertown on Rover, so you’re sure to find the perfect match for your dog! In Chestertown, 94% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.