Dog Walkers in Chestertown, MD

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

1. Taylor

Energetic and Experienced Care

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Taylor is responsible, caring and each dog she has encountered instantly falls in love with her. I can go away for a weekend knowing my sweet Annabelle is in... (more)"

Available this weekend
2. Angelene

Doggy Sleep Over Party

Edgewood, MD, 21040

Dog Boarding, Doggy Day Care

57 repeat clients

"Dimon has weekly daycare with Angelene. This was his first overnight stay. I must say that Angelene by far is the best doggy day care center that any person ... (more)"

3. Kate

Your dog will b loved & never bored

Baldwin, MD, 21013

Dog Boarding, Doggy Day Care

2 repeat clients

"Kate was wonderful! My pups came back happy and tired :-) (more)"

4. Amanda

Dog Walker

Middle River , MD, 21220

Drop-In Visits, Doggy Day Care, Dog Walking

"I’ve used Amanda several times over the past two years and she truly treats my furry child as if he were her own. My job requires long hours and frequent tra... (more)"

5. Maddie

pups, dogs, and elders!

Worton, MD, 21678

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

About: I adore dogs. They're my favorite animal in the world. I provide all the care and attention in the world for your puppy, dog or elder. No matter wh... (more)

6. Nikola

Fur babies are family too!

Abingdon, MD, 21009

Dog Boarding, Doggy Day Care

1 repeat client

"I have known Nikola for over four years and in that time I have been able to witness her excellent care and rapport with pets, particularly dogs. She is ver... (more)"

7. Josahara

Pawdates with Josie

Essex , MD, 21222

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

"I went away for my deployment back in October and I had Josie watch my dog Mary for 3 months while I was away. I felt completely safe leaving Mary with her! ... (more)"

8. Elizabeth

Fur Ever Lover

Aberdeen, MD, 21001

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

2 repeat clients

"I own two cats who are both pretty finicky. One is extremely nervous around strangers but Liz won him over pretty quickly. She is patient and treats your ani... (more)"

9. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

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

2 repeat clients

"Jen has watched my dog and cats several times and she does a great job!!! I have an English bulldog and she requires extra care and cleaning of her face and... (more)"

10. Jessica

Calling all Fur Babies!!!

Abingdon, MD, 21009

Drop-In Visits, Doggy Day Care, Dog Walking

About: I’m available all day to love, cuddle and play with all doggies. My dog loves to play with squeaky balls and tennis balls. So we can play with them... (more)

11. Terry

We Love Pets!

Pasadena, MD, 21122

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

13 repeat clients

About: We have been pet lovers all of our lives. Growing up we had dogs, cats, snakes, chameleons, birds, rabbits, a duck, fish, hamsters...and the list ... (more)

12. Debi

I'm a fur baby fanatic!

MIDDLE RIVER, MD, 21220

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

2 repeat clients

About: I love dogs. All of mine are rescues and I involve myself with various rescue organizations as much as I can. I currently run my own home based bu... (more)

13. Ashley

Farmland for Fun

Essex, MD, 21221

Drop-In Visits, Doggy Day Care, Dog Walking

About: I can travel to you and your dog(s) to walk, feed, groom, play with, and care for your dog. I currently live in White Marsh and am moving to Kingsv... (more)

14. Erin

Let me love yours like my own!

Belcamp , MD, 21017

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

About: I have experience ranging from 2 deliveries with 1 including parvovirus. I've assisted in training our grand and grand champion Pit Bills and have ... (more)

15. Emma

I love long walks with dogs

Bel Air, MD, 21015

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

1 repeat client

About: I've been dog sitting my boyfriend's families dog every time they're not home for quite some time now. Sometimes they'll bring her to my house as w... (more)

16. Jordan

Your Furbaby is part of the family.

Middle river , MD, 21220

Dog Boarding, Doggy Day Care

About: I am a dog lover. I have kids (three years and one year old.) who absolutely love dogs. And always ask to take a dog home. And I do love dogs but d... (more)

17. Tammie

Dog Walking & Pet Sitting Services

Abingdon , MD, 21009

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

3 repeat clients

"Tammie loves animals like they are her own! She is passionate and has a love for animals I have never seen! She has cared for my dog and kitten like they wer... (more)"

18. Kysteina

I'm his human ;-)

Edgewood , MD, 21040

Dog Boarding, House Sitting, Doggy Day Care

About: I grew up with dogs and I now have my own Long-haired Chihuahua, who I love to pieces. I do not have experience as a paid dog sitting, but I have e... (more)

19. Ken

I actually play with the dogs!

Middle River, MD, 21220

Drop-In Visits, Doggy Day Care, Dog Walking

About: For offsite visits, I'm on time and play with the dogs. If using day care, I live off the main road and have a large privacy fenced back yard that ... (more)

20. Christine

My family members have 4-legs

Belcamp, MD, 21017

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

"Christine did a wonderful job sitting for our dogs while we were unable to tend to them. We knew they were in safe and spoiled hands. (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

We've been there: rushing home during every lunch break to take the dog for a quick walk around the block. Good news: You can easily find and book Chestertown dog walking services on Rover. Whether you need a one-time dog walker or someone to take your dog for a stroll every day, we've got you covered. Exercise for your dog and peace of mind for you are just a few clicks away. Every walk is covered by premium pet insurance, at no extra cost to you. You can even ask your dog walker to send you a photo update. Whether you already have a favorite pet sitter on Rover or you're new to the site, we'd love to connect you with a dog walker in Chestertown the next time you're unavailable. We're confident you and your dog will love it.

Wondering what you should be paying for a walk? Check out our standard dog walking rates for a comparison.