Dog Walking Chester

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Over 7
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Chester, Find top rated dog walking

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Bohdanna G.
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Bohdanna G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
81 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: Ashley C.
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Ashley C.
from
$25
per walk
5.0 out of 5 stars
11 reviews
2 repeat clients
10 years of experience
Centreville, MD, 21617

I appreciated her flexibility and text/picture updates

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Meaghan K.
Sitter Profile Image: Alexis B.
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Alexis B.
from
$15
per walk
5.0 out of 5 stars
1 review
1 repeat client
12 years of experience
Grasonville, MD, 21638

Alexis is amazing!! She goes the extra mile and loved on our dogs so well! I will have her back again and again!

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Mari H.
Sitter Profile Image: Brooke F.
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Brooke F.
from
$25
per walk
5.0 out of 5 stars
77 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: Lena M.
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Lena M.
Star Sitter
from
$39
per walk
4.9 out of 5 stars
22 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: Ryan L.
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Ryan L.
from
$27
per walk
5.0 out of 5 stars
9 reviews
1 repeat client
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: Nolan C.
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Nolan C.
from
$15
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Annapolis, MD, 21409

About: I have taken care of different types of dogs and including in home stay, walks, puppies etc and had my own dog since I was 12. I have lots of experience in caring for animals from reptiles to mammals. I am very physically active and love to spend time outside so long walks and exercise is both fun for me and your pet. I am currently looking for a part time job my schedule is open for the relative future and any changes to my schedule will be minimal, I am fully available for a consistent walking or care schedule for your pet. I care for my dog with long walks, exercise/play time with his favorite toys or enrichment games. I also have a back and front yard at my house that my dog loves to play in with a park and beach access that allows dogs. When I care for bigger dogs I love to take them to the park in my neighborhood or one nearby to play fetch.

Sitter Profile Image: Savannah T.
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Savannah T.
from
$20
per walk
5.0 out of 5 stars
10 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: Bryan J.
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Bryan J.
from
$26
per walk
5.0 out of 5 stars
4 reviews
4 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: Courtney A.
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Courtney A.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
18 reviews
7 repeat clients
15 years of experience
Parole, MD

About: Hi! I’m Courtney — a true dog lover, experienced pet caregiver, and someone who treats every pet like family. As a dog mom myself, I understand how important it is to trust the person caring for your pet. Whether your dog loves long walks, playtime, couch snuggles, or just a calm and reassuring presence, my goal is to make them feel safe, comfortable, and loved while you’re away. I have extensive experience caring for dogs with a wide range of personalities, energy levels, and care needs, and I pride myself on being dependable, communicative, and attentive to details. For house sitting, my standard rate includes typical care such as feeding, walks/potty breaks, companionship, overnight care, and lots of love. If your pet requires additional support — including senior care, medication administration, frequent potty breaks (every few hours), mobility assistance, separation anxiety management, or near-constant supervision — please let me know before booking, as these higher-needs situations may require custom pricing to ensure I can provide the level of care your pet deserves. Please be as detailed as possible about your pet’s routine, behaviors, and care needs so I can make sure we’re the right fit. Looking forward to meeting your furry family member!

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: Tracie L.
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Tracie L.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
8 reviews
8 repeat clients
13 years of experience
Owings Mills, MD, 21117

Tracie is amazing. She has saved the day for me a few times already with last minute walks. She is wonderful with my dogs and always takes lots of pictures and gives them lots of love and attention!

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Rebecca F.
Sitter Profile Image: Terri H.
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Terri H.
from
$15
per walk
7 years of experience
Stevensville, MD, 21666

About: Hello! My name is Terri but I usually go by T. I have owned both dogs and cats my entire life. Ive worked as a supervisor at 2 boarding and daycare facilities over the course of 4 years until I ultimately moved into veterinary medicine as a technician at a specialty clinic! So I have a lot of experience and am comfortable around all breeds,sizes, ages, and most (stable) medical conditions. I’ve always had a special place in my heart for animals and promise to provide the best care possible to ensure that your fur baby gets all the love he or she deserves. I’ll treat them like my own and you can rest easy knowing your pet is getting all of their necessities and some extra love along the way. I work as a surgical veterinary technician 5 days a week so walking is a side gig for me on my off time but the more time I get to spend around animals the better :) I promise to follow any particular instructions/tips you have for keeping your pups safe and happy! As well as provide some extra love in the process.

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: Bronte B.
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Bronte B.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
197 reviews
57 repeat clients
15 years of experience
Pikesville, MD, 21208

Bronte is awesome with my pup! When she takes photos or videos, I can tell my dog enjoys her visits and walks! In addition, my stay at home neighbor made a comment about how awesome she was w my dog…,Having fun w her and playing!

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Shelly L.
Sitter Profile Image: Sydney T.
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Sydney T.
from
$30
per walk
5.0 out of 5 stars
10 reviews
6 repeat clients
17 years of experience
Queenstown, MD, 21658

About: I’ve been caring for dogs since I was 12 and can’t imagine life without them! While serving in the Navy, I volunteered at military kennels, and later worked at a doggy daycare/boarding/training facility in Texas. I’m experienced with dogs of all ages, from playful puppies to senior pets, and I share my home with a sweet 10-year-old lab and a 2-year-old Norwegian Forest Cat. Reliable, patient, and attentive — I promise to treat your pets like my own. I have a flexible schedule and lots of love to give! Whether it’s a quick walk or a cozy check-in, I’ll make sure your furry family members get plenty of playtime, cuddles, and attention. I treat every pet as if they were my own, keeping them safe, happy, and comfortable. During walks, I pay close attention to their behavior and surroundings to ensure a fun and secure outing. For in-home check-ins, I follow all your instructions carefully, provide love and attention, and make sure your pets feel relaxed and cared for while you’re away.

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: 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: Emmy S.
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Emmy S.
from
$25
per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
20 years of experience
Stevensville, MD, 21666

Emmy was great with my puppy Chai!

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Richard M.
Sitter Profile Image: Alexxis E.
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Alexxis E.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
29 reviews
9 repeat clients
15 years of experience
Annapolis, MD, 21409

Extremely helpful and flexible with scheduling times. Managed two Siberian huskies with no issue on long walks. Definitely recommend and will use again!

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Keith K.
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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

Marley loves his daily walks, Melanie has been awesome, shows up on time per schedule and provides timely reports on the details of the walk. Extremely satisfied!

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David O.
Dog Walking
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Popular requests for dog walking - Chester

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Sitters in Chester average 4
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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 August 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 August 2026, there are 4,898 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:

  • 92% of walkers can help with special care needs
  • 98% 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 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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