Dog Walkers in Winchester Estates, MD

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

1. Janet

Home full-time fenced yard and pool

Chester, MD, 21619

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

2 repeat clients

"Janet has been in my employ for over seven years. She has taken good care of my dogs as well as performed many different jobs in my garden and home. My dogs... (more)"

2. Amy

Your pooch is gonna love me!

Queenstown, MD, 21658

Drop-In Visits, Dog Walking

About: Hi! I am a mom of 3 human kids, 2 canine kids (Jackson - Bernese Mountain Dog, Phoebe - English Bulldog), 2 feline kids, 2 fish and 4 hermit crabs!... (more)

3. 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)"

4. Ashley

I am available to watch your pups!

Grasonville, MD, 21638

Drop-In Visits, Doggy Day Care, Dog Walking

"Ashley is an amazing mom to her own pets as well as the foster puppies she has cared for in the past. She is always taking them on walks, buying them treats... (more)"

5. Renea

Barker's B & B: A Canine Experience

Edgewater, MD, 21037

Dog Boarding, Drop-In Visits, Doggy Day Care

19 repeat clients

"I can't say enough how amazing Renea is. Daisy was in middle of a very bad cluster of seizures. It is extremely stressful for me and when I have no option ... (more)"

6. Jacob

Sandy Paws Dog Sitting

Edgewater, MD, 21037

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

"Jacob is a long time pet owner and has had pets for most of his life. He has an history with his pets Bailey and Piper. Bailey is a very loving dog and wel... (more)"

7. Bram

Your dog's home away from home

Annapolis, MD, 21403

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

1 repeat client

"Bram was awesome and totally accomodating. He is very caring and attentive as well. His pet dog, Ladybug is also a sweatheart. (more)"

8. Ashley

Experience animal caretaker

Annapolis, MD, 21403

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

"Ashley is a caring and attentive sitter. My dear Flower loved playing with Ashleys sweet Penelope dog (more)"

9. Natalie

Weekend Getaway

Shady Side, MD, 20764

Dog Boarding, Doggy Day Care

7 repeat clients

"This is the second time our dog stayed with Natalie. He ran up to the door & was so happy to see her again! (more)"

10. Pat

I serve ice cream on hot afternoons

Annapolis, MD, 21403

Dog Boarding, Doggy Day Care

68 repeat clients

"She was very flexible while my husband and I took a short notice day trip. She was very accommodating for drop off and pick up time. Our pups ran right into ... (more)"

11. Joanna

Edgewater Pup Palace

Edgewater, MD, 21037

Dog Boarding, Doggy Day Care

3 repeat clients

"Joanna was great! Not only was she INCREDIBLY flexible with drop-off and pick-up (especially when my work day ran 2 hours longer than expected), she took sp... (more)"

12. Erica

Logan's Paws & Play

Annapolis, MD, 21401

Dog Boarding, Doggy Day Care

"Molly had a delightful day with Erica in Annapolis. She saved the day for us as we visited with our new granddaughter. Next visit we will be calling her again. (more)"

13. Jack

Large Fenced Yard + Home Full-Time!

Arnold, MD, 21012

Dog Boarding, Doggy Day Care, Dog Walking

6 repeat clients

"Jack and his kids were great with our two Boston Terriers. We left them with them for a day to acclimate ahead of a 10 day stay later in the month. We were t... (more)"

14. Jennifer

Home full-time, great neighborhood!

Chestertown, MD, 21620

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

About: I am a 30 year old stay at home mom with two miniature dachshunds. They are super sweet and love other dogs and cats. I live in a house with a scre... (more)

15. Elaine

Elaine's Pampered Pets

Annapolis, MD, 21403

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

5 repeat clients

"Elaine is terrific--we are so comfortable leaving Bravo with her and he has a great time!! (more)"

16. Lauren

Fur baby lover

Annapolis , MD, 21401

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

1 repeat client

"Lauren was excellent and took wonderful care of Lady Bug. I will definitely reach out to her again. (more)"

17. Corey

Your dog and I will be best friends

Annapolis, MD, 21401

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

1 repeat client

"Corey has owned and loved dogs for as long as I can remember. She has been dog sitting for years. Coery treats every dog as if it were her own. If I ever nee... (more)"

18. Christa

Love long walks-larged fenced yard!

Annapolis, MD, 21409

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

About: I absolutely adore all dogs! We currently have an 11 month old pug who is our entire world and I would love to help out others by walking their pup... (more)

19. Greg

Dog Heaven in Downtown Easton

Easton, MD, 21601

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

About: If your dogs think they are people, they will fit right in at our place. Your dog will love visiting our little urban homestead. We have a fully ... (more)

20. Heidi

I have a huge heart for pups!

Annapolis, MD, 21401

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

9 repeat clients

"When our dog Finn stays with Heidi, it is like a vacation for him. This is our second time using Heidi and we already booked her for future dates. (more)"

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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 Winchester Estates 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 Winchester Estates 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.