Dog Walkers in Chestertown, MD

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

1. Alexandra

Trustworthy Animal Lover

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: Hello! Thank you for visiting my profile! I am a senior at Washington College who doubles as an experienced pet-sitter! My family has had a dog... (more)

Available this weekend
2. Angelene

Doggy Sleep Over Party

Edgewood, MD, 21040

Dog Boarding, Doggy Day Care

49 repeat clients

"Angelene always does a great job with Bailey!! Bailey is always excited when she gets in the car with me in the morning during the week, because she knows s... (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. Sierra

Experienced Dog Mom - Open Schedule

Middle River, MD, 21220

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

2 repeat clients

"Sierra loves all animals! She is a wonderful caring mother to her own dog! She treats her dog as a child and will do whatever she possibly can in order to ma... (more)"

5. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

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

"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)"

6. Amanda

Dog Walker

Middle River , MD, 21220

Drop-In Visits, Doggy Day Care, Dog Walking

"Amanda is an absolute animal lover! She has always wanted to have a rescue farm so she could take needy animals in and take care of them. She has two small d... (more)"

7. Elizabeth

Fur Ever Lover

Aberdeen, MD, 21001

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

2 repeat clients

"Over the past several years Elizabeth Garcia has assisted me in the care and grooming of my animals. Elizabeth seems to have a special way of communicating ... (more)"

8. Ashley

I am available to watch your pups!

Grasonville, MD, 21638

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

"My two energetic English Coxker Spaniel loved staying with Kelly! They came home happy, call and relaxed! I highly recommend! (more)"

9. Brittney

Love your dog like their my own

Essex, MD, 21221

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

About: I treat and care for you dog/puppy like their my own furr baby. My dog enjoys playing with other dogs and puppies. I want to be responsible so if y... (more)

Available this weekend
10. Emma

I love long walks with dogs

Bel Air, MD, 21015

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

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)

11. Karoline

Your "go to" when you need it

Greensboro, MD, 21639

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

About: I'm a stay at home wife who wants to be your "go to" when you need it. Although new to Rover, I'm not new to dogs and trying to understand them.... (more)

12. 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)

13. 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)"

14. Aleksandra

Playful energetic dog lover!

Stevensville, MD, 21666

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

About: Hello, my name is Aleks. I've had dogs my whole life, and always loved to babysit my friends animals. I love to interact with them like play fetch ... (more)

15. Lacey

Loving family to care for your pets

Perry hall, MD, 21128

Dog Boarding, Doggy Day Care

About: Hi. I'm Lacey. I'm a teacher and I have children in the home with me ages 7,2,7 months. I'm looking to help with summer plans with dog sitting in t... (more)

16. 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)

17. 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)

Available this weekend
18. 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.