Dog Walkers in Chester, MD

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

Available this weekend
1. Wendy

Walk and Play with your dog.

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

4 repeat clients

"Wendy has walked our dogs almost every day for a week and she has been great! She is always on time, leaves us detailed Rover Cards, and always sends us pict... (more)"

Confirmed Holiday Availability
2. Janet

Home full-time fenced yard and pool

Chester, MD, 21619

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"We loved Janet. She and Toby hit it off immediately. She is very reliable and we got a picture during the visit. When we first contacted her she was quick to... (more)"

Confirmed Holiday Availability
3. Caroline

Happy pet , happy life !!!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Caroline was very communicative, always posting pictures of Jack and even sending videos! She always responded quickly to questions also. Many thanks for tak... (more)"

Confirmed New Years Availability
4. Allie

Wagging for walks! Dog lover/owner

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

"Allie was fantastic. Asked thorough questions on meet and greens from house procedures to my dog. She sent photo updates and wrote a solid report on the dog ... (more)"

Confirmed Holiday Availability
5. Norah

Energetic and ready for your dogs

Stevensville, MD, 21666

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"I have known Norah for many years and found her to be a hard and open worker. She will ensure the safety and comfort of your pets and ask questions when need... (more)"

6. Kirsten

I'll run/hike/SUP with your pup!

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Kirsten is amazing with animals! She's owned many different animals, she's worked as a vet tech, she's walked my dog for me, and she pet sits for friends. Sh... (more)"

7. Kate

Must love dogs...Yes, that's me!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Reliable & cheerful (more)"

Confirmed Holiday Availability
8. Carly

Reliable dog walker/ sitter!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"Carly is an active outgoing dog walker. She loves being outside and enjoys taking my dogs on long walks. She has watched my dogs on numerous occasions while ... (more)"

Available this weekend
9. Hanna

I love long walks on the beach

Annapolis, MD, 21403

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Hanna is an excellent dog sitter. She is very compassionate and empathetic so she takes great care. She is very responsible and mindful, so you can leave you... (more)"

Confirmed Holiday Availability
10. Kathleen

Your dog's safety is my priority!

Stevensville, MD, 21666

Drop-In Visits, Dog Walking

"Kathleen has been a trusted and responsible employee of Animal Resource Foundation (ARF) since 2010. Over the years Kathy has proved to be dependable and he... (more)"

Confirmed Holiday Availability
11. Madison

Dependable Doggie Sitter/Walker :-)

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Madison was very sweet and thorough with our 1 year old Crackle. She immediately assessed that he was a little nervous for their first play with out his pare... (more)"

12. Caitlin

flexible student who loves animals

Arnold, MD, 21012

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Caitlin is s hard working, responsible, pet loving individual. She has a fantastic relationship with my lab and watches him frequently. Her love of animals i... (more)"

Confirmed Holiday Availability
13. Mackenzie

Ill treat your dog as my own

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"I have know Mackenzie for over 10 years and she’s always been loving and caring towards any animal . She has walked my shepherd mix chessie multiple times an... (more)"

Confirmed Holiday Availability
14. Sydney

Owner and Lover of dogs

Annapolis, MD, 21403

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Sydney always took great care of my pets and was super quick with responding to texts and calls and could always help at the last minute. Would highly recomm... (more)"

Confirmed Holiday Availability
15. Sarah

For the Love of Dogs <3

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

"I am a lifelong dog lover and met Sarah 6 years ago as she was working at "The Canine Fitness Center" in Crownsville, MD. My dog Honey was rehabilitating an ... (more)"

16. Kareen

Animal Lover

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

1 repeat client

"We have used Kareen several times to take care of our loving dog Oscar when we've been on vacations or during the day if we were hung up with work or other c... (more)"

17. Kelli

Dog lover! Home full-time

Stevensville, MD, 21666

Drop-In Visits, Dog Walking

"Kelli is the best doggy care giver I could ever hope for!! Starting from when my pup, Mulligan, was a young puppy, Kelli has taken care of him. She always co... (more)"

Confirmed Christmas Availability
18. Eilish

FUR MOMMA OF 3! I LOVE ALL DOGS!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Eilish took great care of our doggy and always sent pictures. Would definitely recommend to other owners. (more)"

19. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Words can not express how grateful I am for the wonderful care Jennifer has provided for Maverick, our chocolate lab. Due to my husbands illness, requiring h... (more)"

Confirmed Holiday Availability
20. Leah

Flexible, Will be BFFS w/ your dog!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"Leah really knows what she's doing when it comes to dogs. This girl is the biggest dog lover i know and has always expressed her love for dogs for as long as... (more)"


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!