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

6 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)"

2. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"My Dalmatians Yankee and Sam love there dog walker/sitter... they get super excited when they see her coming: She is punctual, committed and a loving dog wat... (more)"

3. Ashley

I am available to watch your pups!

Grasonville, MD, 21638

Drop-In Visits, Doggy Day Care, Dog Walking

"I would recommend Ashley without hesitation when it comes to being responsible and loving dog caregiver. You will definitely be able to relax and not stress... (more)"

4. Steve and Gin

Precious Pets

Easton, MD, 21601

Dog Boarding, Doggy Day Care

73 repeat clients

"Steve and Gin were gracious with their time and in getting to know Quincy at our 'meet and greet' and took wonderful care of Quincy in his first doggie dayca... (more)"

5. Bram

Your dog's home away from home

Annapolis, MD, 21403

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

5 repeat clients

"We're so grateful that Bram was able to accommodate our last minute daycare request. A kind and attentive sitter, a beautiful home, and a sweet and playful ... (more)"

Confirmed Thanksgiving Availability
6. Natalie

Weekend Getaway

Shady Side, MD, 20764

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

7 repeat clients

"Ginger was so happy to stay with Natalie I was afraid she may not come home with us! We loved the fact that we could stay with Natalie and Steve and they we... (more)"

7. Jack

Large Fenced Yard + Home Full-Time!

Arnold, MD, 21012

Dog Boarding, Doggy Day Care, Dog Walking

19 repeat clients

"Jack and his family were amazing! We were very nervous being away from our puppy the first day, but Jack lessened our fears by sending us frequent photos and... (more)"

8. 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 Thanksgiving Availability
9. Maria

We know about doggone good time!

Annapolis, MD, 21403

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

About: I have a dog myself (Beagle Mix) which I share custody of and I am Deaf myself. I love dogs like they are my children which I do not have any. Rai... (more)

Confirmed Thanksgiving Availability
10. 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)"

11. Pat

I serve ice cream on hot afternoons

Annapolis, MD, 21403

Dog Boarding, Doggy Day Care

72 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)"

12. 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)"

Confirmed Thanksgiving Availability
13. Ashlyn

Large yard and very caring

Ridgely, MD, 21660

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

"Ashlyn has cared for my dog for a few years. My dog is on a special diet and takes medication, and she always provides the best care! She is very responsible... (more)"

14. April

Lifelong dog lover w/o my own

Annapolis, MD, 21403

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

2 repeat clients

"Took great care of my fur baby! (more)"

15. Lauren

Fur baby lover

Annapolis , MD, 21401

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

2 repeat clients

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

16. Penny

Dogs make me happy :)

Annapolis, MD, 21403

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

"Penny would make an excellent pet sitter. Since birth, she has grown up with many different kinds of animals and had the responsibility of taking care of the... (more)"

17. Sam

Who let the dogs out?

Annapolis, MD, 21403

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

"Samantha is very loving to our dog, Bailey. She's responsible, punctual and trustworthy. I trust her with the keys to our house and know that Bailey is get... (more)"

18. Maura

I'll love your pup like my own!

Annapolis, MD, 21403

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

"Maura T. is great with with dogs! Maura has socialized and trained many dogs over the years. Maura uses positive reinforcement and was very knowledgeable wit... (more)"

19. Hailey

Energetic and caring dog care

Annapolis, MD, 21401

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

"Hailey is kind and compassionate dog sitter for my family. We have 2 dogs. Our 16 year old Schnoodle wears diapers and is deaf. Hailey treats her with patien... (more)"

Confirmed Thanksgiving Availability
20. Sydney

The Wag On Inn

Church Hill, MD, 21623

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

4 repeat clients

"Sydney has expertly cared for all of our farm animals: cattle, sheep, goats, cats, and hundreds of chickens at once, but most importantly, she has cared for ... (more)"


When you need dog walking services, we doubt you'll find a better experience than through Rover. Thanks to our wide selection of dog walkers in Winchester Estates, MD, you'll find that you're able to work with a dog walker who fits in with you, your dog, and your needs. With our start-to-finish approach, your walker can supply you with real-time dog walking updates with start and stop times, a GPS map of their walk, info about any bathroom, food, and water breaks, and pictures of what your dog's been up to. And on top of that, each Rover dog walking booking includes premium pet insurance, 24/7 support, and a reservation guarantee.

And even better: the price of dog walking in Winchester Estates, MD might not be as much as you thought. Whatever your price range, you'll find a dog walker on Rover for almost any budget. Interested in finding out what the typical Rover dog walker expects as a dog walking fee? Visit our average dog walking rates to see the general fees before checking out an individual dog walker's rates.

Looking for a quick solution to your dog walking needs when you're short on time? Then you'll love the Rover dog walking app. The Rover app features hundreds of highly rated, trusted dog walkers, and you can scroll through the options or simply rebook your regular dog walker in seconds. Your dog walker can share real-time photo updates via the Rover dog walking app, and with the app's cashless payment feature you'll be able to compensate your dog walker quickly and safely - no need for cash, checks or tips.

Need to find a dog walker near Winchester Estates, MD? Rover.com is the easy, effective way to discover and book reliable dog walking services. The Winchester Estates walkers on Rover love dogs, and 95% of reviewed stays and walks have received a perfect five-star rating. We also offer background checks to all Rover dog walkers in Winchester Estates, MD to ensure that you have total peace of mind - just look for the background check badge on your walker's profile.

In other words, when you use Rover to find Winchester Estates 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!