Dog Walking Chester

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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: Brigid S.
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Brigid S.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 10 reviews
2 repeat clients
18 years of experience
Chester, MD, 21619

About: I've always been the go-to gal for my friends and family who need care for their pets. I've made many furry friends over the years. I'm a freelance writer with lots of freedom to come and go, so my schedule is pretty flexible. If you need pet care on short notice, I'll do my best to accommodate. Your pet can enjoy the comfort of its own home while I come over and cater to their needs. We'll become the best of friends!

Sitter Profile Image: Brooke F.
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Brooke F.
from
$25
per walk
5.0 out of 5 stars
• 79 reviews
18 repeat clients
10 years of experience
Chester, MD, 21619

“What a fantastic person ❤️! We were super lucky to have Brooke walk Tank. She was punctual for every walk. Definitely recommend her. And will use her services again.”

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Donna T.
Sitter Profile Image: Jason & Tracy Y.
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Jason & Tracy Y.
from
$15
per walk
4.9 out of 5 stars
• 78 reviews
32 repeat clients
10 years of experience
Stevensville, MD, 21666

“Thank you!!”

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Erin H.
Sitter Profile Image: Bryan J.
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Bryan J.
from
$26
per walk
5.0 out of 5 stars
• 7 reviews
5 repeat clients
20 years of experience
Chester, MD, 21619

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

Sitter Profile Image: Anna B.
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Anna B.
from
$15
per walk
5 years of experience
Kent Island, MD, 21619

About: I’ve had dogs in the house for my entire life. I would frequently volunteer at the animal shelter during college and help out with dog walking there as well. I work flexible hours at my hybrid job! I can easily make time for your animal multiple times a day if needed. I have reliable transportation as well. I will feed, walk, and provide plenty of enough play and physical activity for your dogs. Willing to do overnights and coming multiple times a week.

Sitter Profile Image: Bohdanna G.
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Bohdanna G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 84 reviews
28 repeat clients
25 years of experience
Stevensville, MD, 21666

“Gus, my dog loves you he is alway well taken care. Communication is always great thank you so much for caring for Gus. and I feel comfortable”

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Dawn M.
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: Hannah P.
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Hannah P.
from
$20
per walk
5.0 out of 5 stars
• 8 reviews
1 repeat client
10 years of experience
Chester, MD, 21619

About: Hi, I’m Hannah — a responsible, caring pet sitter who treats your home and pets like my own. I know how difficult it can be to leave your furry family member behind, so I’m here to give you peace of mind with loving, attentive in-home care. Whether your dog needs belly rubs, playtime, medications, or a quiet companion on the couch, I adapt to their unique needs and stick to their usual schedule. I’ll also keep your home tidy and safe so you can return to everything just how you left it (or better!). ~Staying overnight at your home ~Feeding, walks, and potty breaks on your schedule ~Playtime, snuggles, and companionship ~Administering medication (if needed) ~Daily updates with photos and notes ~Light home care (mail, plants, trash, etc.) ~Respectful, clean, and professional behavior in your space Hi! I’m Hannah, a very energetic stay-at-home mom. I can’t wait to welcome your pets into my life! I'm home full-time this summer, so your dogs or cats will get constant attention, affection, and supervision while you’re away. I'm a huge animal lover — patient, kind, and great at following routines. Whether your pet needs playtime, snuggles, walks, or quiet companionship, I'll provide a safe, loving environment that feels like home. Our animals are happiest in their environment with their familiar smells, toys, and routines. I help minimize stress and keep them comfortable while you enjoy your time away, worry-free.

Sitter Profile Image: Savannah T.
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Savannah T.
from
$20
per walk
5.0 out of 5 stars
• 12 reviews
5 repeat clients
1 year of experience
Stevensville, MD, 21666

About: I am currently employed as a kennel attendant and a veterinary assistant where I have gained experience in dog handling, feeding, medicating, and more. I have experience with dogs of all sizes, breeds, and temperaments. I am currently working part time at 2 jobs attending college. My schedule changes weekly but I always have extra time to watch your pups! I am located on Kent Island and I am not able to provide services over the Bay Bridge. I am not currently offering boarding in my home however I would be more than happy to watch your animals in your house.

Sitter Profile Image: Lena M.
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Lena M.
Star Sitter
from
$39
per walk
5.0 out of 5 stars
• 26 reviews
7 repeat clients
20 years of experience
Stevensville, MD, 21666

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.

Sitter Profile Image: Mary L.
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Mary L.
from
$30
per walk
4.9 out of 5 stars
• 36 reviews
16 repeat clients
30 years of experience
Stevensville, MD, 21666

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!

Sitter Profile Image: Gina G.
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Gina G.
from
$15
per walk
20 years of experience
Grasonville, MD, 21638

About: As a mom and lifelong animal lover, I understand how important trust is when someone cares for your pet. I offer dependable, attentive care in a calm home setting. I’m patient, nurturing, and detail-oriented — making sure your dog feels loved, exercised, and safe at all times. My open schedule allows for consistent supervision and care. I’m flexible with my time and available most days and weekends which allows attentive care :) I care for pets in my home, offering a secure and relaxed setting while you’re away. They will be comfortable safe and always loved :)

Sitter Profile Image: Cristina M.
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Cristina M.
from
$25
per walk
5.0 out of 5 stars
• 9 reviews
25 years of experience
Stevensville, MD, 21666

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.

Sitter Profile Image: Lindsay G.
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Lindsay G.
from
$15
per walk
5.0 out of 5 stars
• 2 reviews
3 years of experience
Chester, MD, 21619

About: I have been a pet care attendant at a dog kennel for two years now. My responsibilities include feeding, walking, playing, bathing/grooming, and administering medications for animals. I have training in dog behavior as well as any medical needs of animals. I also come from a veterinary medical background and have watched and walked dogs for members of my community for many years. I have experience dealing with aggressive, dog reactive, leash reactive, cage brave, and resource guarding animals as well as any other needs that your pet may have. I am currently enrolled at the University of Maryland but can make time to walk and care for pets around my school schedule. I am at my apartment all other times of the day and will be easily available to care for pets. I live in an apartment currently but can easily crate your animals when leaving for class. I live in a pet friendly community with no others pets living in my apartment and can easily walk your pet around my community or take them to the courtyard in my apartment for a quick potty break. There is also an animal bathing room in my apartment complex so I am able to bathe your animals if needed.

Sitter Profile Image: Carmel S.
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Carmel S.
from
$23
per walk
5.0 out of 5 stars
• 16 reviews
2 repeat clients
5 years of experience
Grasonville, MD, 21638

About: Hello everyone, I’m back and accepting new clients once again! I am Reliable and experienced sitter/walker ensuring your canine companion gets the exercise and attention they need. Tailoring visits to suit each dog's energy level and personality for a joyful experience. Pet Sitter: Trustworthy care for your furry friends while you're away. Offering personalized attention, exercise, and companionship to keep your pets happy and healthy. Experienced in caring for special needs dogs! I work part time and I’m in school but I have some free time and would love to fill it by providing care for your pet 😄 I generally accept last minute bookings unless I genuinely will not be able to provide proper care. I will pick up/drop off your pet no matter what side of the bridge you live on-don’t hesitate to ask! I genuinely love dogs and will go out of my way to make sure their needs are met. I currently live in a house in Grasonville with lots of property and grass. It is on the water with a lot of trails for some nice dog walks! I tailor each visit to suit the individual dog’s needs.

Sitter Profile Image: Kate M.
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Kate M.
from
$25
per walk
4.8 out of 5 stars
• 5 reviews
2 repeat clients
32 years of experience
Chester, MD, 21619

About: I absolutely love animals. I currently have a black lab and I love to just spend time cuddling with her, or going for long walks. If possible, I try to bring her along (assuming they get along at the meet and greet). I’ve noticed that dogs can wear each other out a lot faster than I can, and probably have more fun doing it too. Maddie gets along with everyone and just loves to meet someone new. For your dog, I will treat him/her as my own. I will play with them and take them for walks. I have no problems cleaning up messes, sometimes accidents happen. Let me love and take care of your pet so you don't have to worry about them during the day. Why I love dog sitting I've always been an animal lover. I've had dogs all my life and had two of my own. They truly are the best things that ever happened to me. I’m very active, so I would spend as much time outside as possible with your fur baby. My experience administering medication: I am fine with administering medication, but would like to have the owner show me the correct way of doing it before I start.

Sitter Profile Image: Ryan L.
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Ryan L.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
• 15 reviews
4 repeat clients
25 years of experience
Annapolis, MD, 21409

“Highly recommend Ryan! He took the time to do a meet and greet and really understand my dog’s specific needs. He was very communicative and flexible whenever any changes came up, which I truly appreciated. What stood out most was how he followed my dog’s training routines and even used the exact phrases we’ve been working on. He handled my dog’s reactivity with care and confidence, and it made a huge difference. I felt completely at ease knowing my dog was in such good hands!”

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Stacie Z.
Sitter Profile Image: Elizabeth S.
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Elizabeth S.
from
$15
per walk
5.0 out of 5 stars
• 2 reviews
1 year of experience
Stevensville, MD, 21666

About: I lived around both dogs and cats my whole life, with both family and roommates, and I absolutely love it. While I'm not in the position to have my own furry friend at the moment, I love to care for animals. I spent about a year (2025) volunteering with the MCACAC shelter cats and dogs in Christiansburg, including participating in their training courses, and now feel confident bringing that experience to work with pets that already have found their families as well. I currently work part-time and unfortunately my hours change every week, so I can't take on consistent requests at the moment. I am still available to schedule individual week-of appointments, but I cannot guarantee availability more than one week out. As far as working with pets in your home, please let me know your house rules. I generally use whatever items the pet uses at home (leash, treats, etc) for the sake of consistency for the pet and pet parent.

Sitter Profile Image: Aliciya M.
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Aliciya M.
from
$20
per walk
1 repeat client
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: Sean K.
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Sean K.
from
$20
per walk
5.0 out of 5 stars
• 1 review
1 repeat client
10 years of experience
Stevensville, MD, 21666

“Sean does a great job taking care of our dog! He is super reliable and he ensures we stay in communication.”

Profile image
Meghan D.
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The median cost per walk for dog walking in Chester is $20

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Popular requests for dog walking - Chester

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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 on Rover is $22 per walk as of October 2026. Most bookings cost between $22 and $23 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 4,955 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 a map of the walking route , the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Chester after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the walk begins.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to 25,000 in eligible veterinary care reimbursement.

Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to 25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

Yes, you can find walkers who have experience with handling special pet needs in Chester. On Rover:

  • 92% of walkers can help with special care needs
  • 97% can help with giving oral medications or injections
  • 96% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet .

walkers on Rover set their own cancellation policy , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.

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