Dog Walkers in Chester, MD

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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Confirmed availability: Christmas and New Year's
Sitter Profile Image: Heather & Jennifer T.
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Sitter Profile Image: Heather & Jennifer T.
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1.

Heather & Jennifer T.

Trusted Pet Care Provider
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
5.0
12 reviews
3 repeat clients
from
$18
per walk

Heather and Jennifer were genuinely kind, caring, and attentive to Gizmo and Cinci, who are senior dogs. This is my first time in 14 years using a dog walking service for the boys, and I am really happy that I chose them. They were very professional, responsible, and reliable!

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Sitter Profile Image: Sabrina G.
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Sitter Profile Image: Sabrina G.
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2.

Sabrina G.

Personalized Pet Care Specialist
Wye Mills, MD, 21640
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4.5
12 reviews
4 repeat clients
from
$25
per walk

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

Sitter Profile Image: Jennifer D.
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Sitter Profile Image: Jennifer D.
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3.

Jennifer D.

I love animals!!
Grasonville, MD, 21638
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
138 reviews
21 repeat clients
from
$25
per walk

Jennifer is awesome! She was very communicative and willing to walk our dog with somewhat short notice. She sent great updates and pictures. We will definitely be booking her again!

Sitter Profile Image: Robin A.
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Sitter Profile Image: Robin A.
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4.

Robin A.

Kind, responsible and strong.
Chester, MD
Drop-In Visits, Dog Walking
1 review
2 repeat clients
from
$20
per walk

Robin has been super responsive to requests and Marley loves his walks!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Cristina M.
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Sitter Profile Image: Cristina M.
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5.

Cristina M.

Cat & Dog Whisperer for hire!
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$30
per walk

Cristina is likely the best choice for your pet! You likely won't find a more loving and caring caregiver for your pet. I have two little shih tzus that usually stay right with me... but they just light up whenever Cristina comes into the house and she has their full attention - and importantly, they get her full attention :)

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Sitter Profile Image: Kelly K.
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Sitter Profile Image: Kelly K.
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6.

Kelly K.

Happiest to care for your pet!
Annapolis, MD, 21403
House Sitting, Drop-In Visits, Dog Walking
5.0
4 reviews
from
$18
per walk

Kelly did a great job taking care of my special four legged friend. She is conscientious, polite, professional, reliable, and caring. I highly recommend Kelly

Sitter Profile Image: Jackson H.
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Sitter Profile Image: Jackson H.
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7.

Jackson H.

I love taking care of pets.
Stevensville, MD, 21666
Drop-In Visits, Dog Walking
5.0
36 reviews
7 repeat clients
from
$18
per walk

Jackson is doing great walking Dottie. If any issues arise he immediately responds and makes any necessary changes. He alerts me well in advance if he needs to tell me he’s unavailable at future times. He’s doing great!!

Sitter Profile Image: Katie H.
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Sitter Profile Image: Katie H.
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8.

Katie H.

I like big mutts and I cannot lie!
Grasonville, MD, 21638
House Sitting, Drop-In Visits, Dog Walking
5.0
2 reviews
1 repeat client
from
$24
per walk

Katie showed up on time and did a great job with our Marley! Couldn’t ask for better service!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Jennifer M.
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Sitter Profile Image: Jennifer M.
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9.

Jennifer M.

Running with the Big Dogs!
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$15
per walk

Jennifer has been great to my dogs over the years! I was pleased to hear that she has decided to branch out. I give her an 11/10- highly recommend.

Sitter Profile Image: Gregory G.
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Sitter Profile Image: Gregory G.
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10.

Gregory G.

Fenced Yard | Home Full Time
Stevensville, MD, 21666
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
53 reviews
12 repeat clients
from
$25
per walk

About: Hey guys, my name is Greg, I have been working from home for about 6 years now, as such I am fairly flexible with availability. I am an animal lover at heart, I have had both dogs and cats all of my life. I have been sitting for rover for a total of 3 years. I have loved meeting and caring for a wide array of breeds in all sizes. Currently, we have one dog (German Short Haired Pointer, who has lots of energy and loves to play) and two cats (Russian Blue and Domestic Short Hair, who generally stick to themselves), which I am sure you will see in the pictures. They are both very good with other animals. Please note if boarding I do require adequate food to be provided by the owners for the duration of the stay. I can't wait to meet you and your pets! Thanks again for trusting and choosing me to be a part of you and your pet's life! If you have any questions or concerns please do not hesitate to ask. As I work from home full time, I am relatively flexible in scheduling visits. Even if there are multiples required. I do stay for the scheduled duration and provide many pictures as well. There will always be someone at the house to play, feed, and care for your little one. Additionally, I have one dog that loves to entertain his playmates. Regarding drop-in visits I respect your home as if it were mine. I have been working from home since before COVID started. Which allows me a great deal of flexibility for drop in visits and dog walks. I have a large fenced yard (1/3 Acre) with plenty of room to run and play. My German short-hair pointer is 5 years old and loves to chase and be chased as well as play fetch.

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Sitter Profile Image: Morgan O.
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Sitter Profile Image: Morgan O.
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11.

Morgan O.

Responsible Animal Lover
Chester, MD, 21619
Drop-In Visits, Dog Walking
5.0
30 reviews
5 repeat clients
from
$20
per walk

Morgan is wonderful and very professional. She took care of our 3 month old puppy and was updating us all the time. We are new puppy parents and were very worried for the first couple times, but Morgan made sure we got constant updates and pictures. And puppy was very happy every time! High recommendation!

Sitter Profile Image: Callie C.
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Sitter Profile Image: Callie C.
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12.

Callie C.

Rover 101
Live, Love, Bark!
Grasonville, MD, 21638
House Sitting, Drop-In Visits, Dog Walking
5.0
3 reviews
1 repeat client
from
$20
per walk

Usually I am skeptical about leaving Sasha, my two year old husky with a sitter due to her separation anxiety(on top of her off-the-chain energy levels) but I can definitely say I was impressed with Callie's level of commitment to my pup. Sasha came back to me not only with a literal smile on her face but with an almost confliction to leave her new friends behind. I will certainly be bringing her back soon.

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Sitter Profile Image: Bohdanna G.
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Sitter Profile Image: Bohdanna G.
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13.

Bohdanna G.

Rover 101
I Love Furbabies!
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
5.0
61 reviews
24 repeat clients
from
$20
per walk

Great as always!!

Sitter Profile Image: Mary L.
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Sitter Profile Image: Mary L.
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14.

Mary L.

Chickens Squirrels Dogs & Kitties!
Stevensville, MD, 21666
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
18 reviews
8 repeat clients
from
$35
per walk

Mary is the ultimate animal lover. I’ve known her for nearly 20 years and she’s always had at least one beloved pet. She knows how to care for a menagerie of animals and has rehabbed countless animals over the years. You couldn’t choose a more conscientious pet sitter than Mary!

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Sitter Profile Image: Jason & Tracy Y.
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Sitter Profile Image: Jason & Tracy Y.
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15.

Jason & Tracy Y.

Rover 101
Reliable & Responsible, Dog Lovers!
Stevensville, MD, 21666
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
62 reviews
26 repeat clients
from
$15
per walk

Jason always does such a great job. Charlie loves when Jason comes over😄

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Brooke F.
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Sitter Profile Image: Brooke F.
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16.

Brooke F.

Pet Nanny by trade!
Grasonville, MD, 21638
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
3 reviews
3 repeat clients
from
$15
per walk

About: I have been walking/sitting all sized dogs for 10+ years simply because dogs make me happier than anything else! I consider myself affordable so you can work away from home with ease knowing your dog won't be in a kennel all day long! I also dog sit/house sit if you need to go away for business or vacation and can not take your 4 legged friends with you. I am trustworhty and dependable so you do not have to worry about a stranger coming in for your dog but more so your dogs BFF coming in to let the out for a little and play and to use the bathroom for a potty break! I hope to talk to you soon and meet your furry friend(s)! I am home almost all day everyday so my schedule is pretty open and I am extremely flexible to accommodate your schedule as well if needed! I have a fenced in big back yard and a very friendly 3 year old lab to accompany your dog! Frequent let outs and frequent cuddle seshs!

Sitter Profile Image: Michael S.
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Sitter Profile Image: Michael S.
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17.

Michael S.

It will be as if you never left!
Chester, MD, 21619
Drop-In Visits, Dog Walking
5.0
7 reviews
1 repeat client
from
$20
per walk

About: I’ve been devoted to my animals my entire life. Trusted for years to look after family and friends pets when they have to leave town. I also work from home so I’m able to give my pets as much attention as they could possibly want. I am currently starting an online business so I make my own schedule, assuring I can take my time and make sure things are done correctly and giving your pet the best care imaginable. Guaranteed. I live in a single family home with a nice fenced in yard. My wife and I have both a spoiled cat and dog that have our whole hearts. But there’s always room for more!

Sitter Profile Image: Bill A.
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Sitter Profile Image: Bill A.
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18.

Bill A.

Pets and your home are safe with me
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
10 years of experience
from
$15
per walk

About: I really enjoy working with pets not only to play, but to train with them. I like walking and being outdoors and pets make it more fun for me. I currently telework full time so pet care is very easy for me to work into my schedule. I also enjoy fitness so being outside with pets it great for me. I have a job that requires the highest of trust so caring for you pets and property will be of the highest priority for me. I will respect you, your pets, and property.

Sitter Profile Image: Donna M.
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Sitter Profile Image: Donna M.
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19.

Donna M.

Ferrets to horses - I got ya 😍
Chester, MD, 21619
Drop-In Visits, Dog Walking
1 review
from
$25
per walk

Donna goes above and beyond with my nervous dog. She’s so patient and kind to his quirks and shyness. He loves Donna and her beagles! She’s so responsive and sends photos and even some videos.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Sarah N.
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Sitter Profile Image: Sarah N.
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20.

Sarah N.

Loving and open arms to any animal!
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
4.5
4 reviews
1 repeat client
from
$15
per walk

Sarah is great with animals. Her family has had pets for many years. Our older dog is anxious and not always comfortable around everyone. Sarah is very helpful with him. He looks forward to seeing her and sitting with her when she comes to our house. We are very comfortable leaving our dogs in her care when we are our of town. She is reliable and trust worthy. She has also helped others with their animals and I have heard good things from the as well. She would be a great sitter for anyone's pets.

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Chester Dog Walking ratings

Overall Rating:

Dog walkers in Chester are rated on average 5 out of 5 stars based on 41 reviews.


When you book dog walking services on Rover, you'll be able to connect with a dog walker who's a good fit for you, your dog, and your lifestyle. Your walker can provide dog walking updates with start and stop times, a map of their walk with total distance, info about pee, poo, food and water breaks, and photos of your dog in action. Every walk booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee.

You'll also be able to relax when it comes to price, because the cost of dog walking in Chester, MD is surprisingly reasonable. No matter your budget or lifestyle, there's a dog walker on Rover to match your budget. Wondering how much most people pay for Rover dog walking services? The average dog walking rates will give you a good sense of what to expect before checking out the individual dog walkers' rates.

If you need to book a great dog walker on the go, you'll love the Rover dog walking app. You can browse hundreds of pre-reviewed, trusted dog walkers in minutes from your phone, and rebook your favorite walker with just a few taps. You'll get photo updates from your dog walker which can be shared via the Rover dog walking app in real time. The app's cashless payment feature allows you to pay your dog walker easily and securely - no cash, checks, or tips.

When you're looking for dog walkers near Chester, MD, Rover.com is the simple, smart way to find and book dog walking services. Our Chester dog walkers are dog lovers first and foremost, and 95% of reviewed stays and walks have received a perfect five-star rating. Every new Rover dog walker in Chester, MD must complete a free background check. You can see the background check badge on your dog walker's profile, so you know your pet is in safe hands. Whether you need to hire a dog walker for a single outing or want someone to go on regular dog walks with your pet, you're sure to find a great fit for all your dog walking needs in Chester with Rover's dog walking services.

In other words, when you use Rover to find Chester dog walking services, your pet is given the best in loving care and hands-on attention, and you don't need to miss out on that just because life got in the way.

Do you think you have what it takes to become a dog walker for Rover? We're always looking for people with a passion for dogs to join us as a dog walker! If you've been thinking about starting up your own dog walking business, or even if you've been doing it on your own for a while, you'll want to check out our easy sign-up process and consider joining the hundreds of awesome dog lovers who use the Rover dog walking platform. When you become a Rover dog walker, you get access to great support, including premium pet insurance, cashless payment (no more worrying about whether you'll get paid on time), and a third party background check to demonstrate your trustworthiness to prospective clients. Join our pack today!

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