Dog Walkers in Windyhill, MD

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

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Top rated Windyhill dog walkers

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Grace F.
Verified Background Check
Grace F.
from
$15
per walk
5.0 out of 5 stars
15 reviews
5 repeat clients
22 years of experience
Easton, MD, 21601

About: Hi my name is Grace F. I've been around dogs and other animals all my life.I currently work at Merck in Millsboro but previously worked at Savannah Animal hospital and Humane Animal Partners. I have experience with dog handling, and doggy daycare. I've dealt with every size dog from my years of dog experience. And numerous ages. Ways you can stay in contact with me is through my cell phone or email. I am open to doing overnights, visits, and walks. I've worked with dogs with aggression towards other dogs before. I have experience with giving prescription medicine through pills and needles. I live in Easton, MD but am willing to travel. Any questions feel free to ask me :) I currently work at Merck in Millsboro so I can only do sittings on the weekends, but I usually work from 6am -2:30pm. Thank you I unfortunately can’t have any dogs at my home, I can only watch dogs from your home. But I will take the best care of your pets.

Sitter Profile Image: Kirsten R.
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Kirsten R.
from
$20
per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
10 years of experience
Easton, MD, 21601

About: I am a college student looking for a part time job. I have taken care of dogs ever since I was a little girl. I took care of the family and the neighbor's dog. I would feed, walk, and occasionally give them baths. I have always loved taking care of animals and would love to take care of your beautiful pets. I’m currently at UNG, I mostly have online classes and have a lot of free time when I’m not at work. I take care of my three dogs and I take them on walks everyday. When I come to your home, I will ensure that your puppy gets all the love it needs. I will feed the puppy if needed and make sure that the puppy will not run away.

Sitter Profile Image: Imani W.
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Imani W.
from
$15
per walk
5.0 out of 5 stars
1 review
20 years of experience
Easton, MD, 21601

Imani is great and very considerate.

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Sayre M.
Sitter Profile Image: Marie W.
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Marie W.
from
$28
per walk
5.0 out of 5 stars
126 reviews
24 repeat clients
17 years of experience
Easton, MD, 21601

Marie has been invaluable to the growth and happiness of my puppy black lab! She consistently goes above and beyond with him, and has always been very consistent and flexible when I need to change our scheduled times/dates. She always leaves my dog satisfied, and I am very grateful that I found her for my baby! I highly, highly recommend her dog walking services. She takes him on various routes in my neighborhood to explore and she always makes sure that he has the exercise he needs, even in the rain!

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Jammie Y.
Sitter Profile Image: Jessica B.
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Jessica B.
from
$20
per walk
5.0 out of 5 stars
15 reviews
2 repeat clients
14 years of experience
East New Market, MD, 21631

About: Experience with multiple breeds of dogs. My heart is owned by our 5 boys and our 3 furbabies 16 year old Siberian Husky named Lola, a 2 year old husky/german Shepard mix named Skye and a 13 year old Australian shepherd named Apache . Firmly believe that pets are family and that it’s up to us humans to provide them with the best life possible. Without a doubt, I will treat your pet family members as if they were my own, with an abundance of love and attention. I know what it’s like to have a good pet sitter and I’ve been very fortunate to know what it’s like to have a peaceful vacation without worries, let me be the one to ease your mind when it comes to your pets care. I’m always doing something doggie related. In addition to Rover we also offer dog grooming so we stay pretty busy with the pooches every day of the week. I have crates to accommodate all sizes of pups for those that are crate trained. Those that need a human bed to sleep in, I’ve got plenty of those as well. Huge yard for lots of exercise.

Sitter Profile Image: Heather M.
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Heather M.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
54 reviews
19 repeat clients
12 years of experience
Linkwood, MD, 21835

Heather is a natural!! She was very calm and relaxed around my dogs. Even my little guy warmed right up to her and he hates everybody!! ?? I will definitely be using her for all my walks, visits and sitting needs. Thank you Heather!!

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Melissa G.
Sitter Profile Image: Chloe T.
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Chloe T.
from
$25
per walk
4.9 out of 5 stars
8 reviews
1 repeat client
17 years of experience
Easton, MD, 21601

About: Hi! I’m Chloe, a reliable and caring pet sitter with a genuine love for animals of all kinds. Whether your pet needs daily walks, playtime, or just some extra affection while you’re away, I’m here to make sure they feel safe, comfortable, and loved. I’m attentive, patient, and experienced with pets who have special routines or unique personalities. Your furry family member will be in good hands! Im a Healthcare worker, beach lover and enjoy cruising in my Jeep. Doggy Daycare is $25 a hour for all day, min 8 hours. $32 an hour for less then 8 hours. Available Fridays,Saturdays and Sundays some mondays. I do work Tuesday Wednesday Thursday 12 hour shifts but I wouldn't mind stopping over before work or after work. I will treat pets like they are my own. I will feed them,play with them and make sure they are comfortable and happy before I leave.

Sitter Profile Image: Rebeka C.
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Rebeka C.
from
$30
per walk
4.8 out of 5 stars
21 reviews
5 repeat clients
20 years of experience
Easton, MD, 21601

This was our first time using Rebeka and she was phenomenal. Not only did she make arrangements at work to walk my dog super last minute but she was very sweet and conscious of my dog’s anxiety around other dogs. We will definitely be using her again! I have already referred her to family and friends.

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Ashley D.
Sitter Profile Image: Katelyn S.
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Katelyn S.
from
$30
per walk
5.0 out of 5 stars
18 reviews
1 repeat client
20 years of experience
Trappe, MD, 21673

About: With over 20 years of hands-on experience caring for dogs of all breeds, sizes, and personalities, I bring more than just basic pet care—I offer genuine companionship and a deep understanding of canine behavior. Whether it’s a high-energy puppy who needs structured walks or a senior dog who craves gentle attention and routine, I tailor each visit to your pet’s unique needs. My background includes working with rescue dogs, administering oral medications, and handling multi-dog households with calm confidence. While growing up, I lived in a home with multiple dogs and have cared for many dogs around my community. I currently own four dogs, two miniature dachshunds, one cane corso and my senior german shepherd. I have spent many of hours training my dogs, especially the cane corso who was a tad reactive, and they are all doing great! I would love to continue helping out around the community to care for your companions. I am currently working a full-time job in Easton, MD from 9-4:30 Monday through Friday. I would be open for mornings, evenings, and weekends. Sometimes, I am totally able to pop out for lunch time walks if it’s in Easton and know ahead of time. I am pretty flexible! In my home, I have three dogs that are crate trained and one that roams the home. I currently have a fenced in yard for my dogs as of recently, but have many years of experience with leashed walks and leash training with my own dogs and client’s dogs.

Sitter Profile Image: Maura M.
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Maura M.
from
$20
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
7 years of experience
Easton, MD, 21620

About: My husband, William, and I have 7 years experience with raising high drive working dogs starting as young as 8 weeks. We feel well equipped to provide the highest level care for your furry loved one while maintaining any training goals. Your dogs comfort and safety is our highest priority so we will try to match your dogs schedule to the best of our ability. I am currently offering care on my days off allowing me the opportunity to have a flexible schedule to fit your dog’s needs during both week days and weekends. I have a 6 foot fenced in yard for your dog to have some safe off leash playtime. Your dog will be home with our residential dog, Duke, during their visit. Duke is an intact male Labrador, so if your dog is in heat, we will keep them separate. All dog gear (toys, water bowls, etc) will be thoroughly cleaned between dog visits to prioritize the health and safety of your dog.

Sitter Profile Image: Gabby G.
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Gabby G.
from
$30
per walk
5.0 out of 5 stars
2 reviews
17 years of experience
Preston, MD, 21655

About: I have been around dogs my whole life. I will take care of your dog like they are my own. I love dogs I have fun taking care of them throughout their whole lives from 3 months to 12 years old. I have experience dog sitting. I am willing to stay at your house while you go on vacation or a business trip. I currently work Monday-Friday but I am available through out the week still. I get off earlier some days and I work later some but I am willing to go let your dog out before I go to work. I am available on the weekends as well. I have 4 dogs at my home 2 black labs, 1 chocolate lab and a little mixed dog. We have a fenced in back yard for them we also live on 20 acres that they are trained so we do not ever have to worry about them wandering off. I will gladly walk your dog on a leash if needed. My dogs are very friendly with new dogs coming to their home as well.

Sitter Profile Image: Emily T.
Verified Enhanced Background Check
Emily T.
from
$20
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
13 years of experience
Trappe, MD, 21673

About: Current Veterinary Technician (2 yr) Previous Veterinary Assistant (1 yr) Recent University of Maryland graduation with a Bachelors of Animal Science degree - Pre Veterinary track Current veterinary school applicant Current animal care assistant of University of Maryland Avian Behavioral Neuroscience Laboratory Pending Masters of Animal Health and Industry program Life long pet experience - various species, breeds, sizes, and demeanors I value the importance of not only caring for pets on visits, but also in spending time engaging in enriching and quality time - it is just as important as potty breaks and feeding times! I am confident in my ability to accommodate each client and pets personal needs and routine! I do work during the week (Mon-Fri). Depending on the pet and owners permission I have the ability to bring my pets to the work with me in the veterinary hospital. Otherwise, I am able to be around weekends and drop in morning and evening (noon if in Easton, MD), and overnights if arranged I follow deeply to clients request, I encourage leaving a note/list of needs, directions, requests! It’s very handy and personable to my care for you and your pet!

Sitter Profile Image: Kristin R.
Verified Enhanced Background Check
Kristin R.
from
$25
per walk
5.0 out of 5 stars
27 reviews
7 repeat clients
29 years of experience
Hurlock, MD, 21643

About: I have taken care of cats and dogs my entire life. My family has always had pets, and I’m a natural pet lover. About two years ago I got my first domestic bunny, and now have two (of course Humphrey needed a bunwife). So I am experienced in bunny care as well. I am so excited to gain your trust by treating your fur babies like my own, and promise to make you feel secure leaving them with me! My schedule is pretty flexible. I babysit for a family in Preston three days a week but the times vary. It evens out to about 18/20 hours spread throughout three days so if your pet is here during those days they may be here without me for a few hours. My fiance does help when he’s off of work so as long as he’s home they would have him too. I own my home with my fiance, and we have a fenced in yard. The fence is about half of the height of your typical fenced in yard, so if your pet is curious and you think they would jump it we can accommodate a lead for your pet to be on just in case. This way they can still get the exercise and freedom a fenced in yard would provide. If your pet is used to going on walks, let me know so we can keep that same routine here. All outside playtime will be supervised as well. Our home contains a very friendly lab who is two and very high energy and gets excited easily, an older chihuahua mix (around 14 years old) and a middle aged chihuahua mix (6 years old). All pets in my home are vaccinated. I am also a nursing student and my boyfriend is a police officer, so we like to think this helps make us trustworthy and professional people who will give you peace of mind while you’re away.

Sitter Profile Image: Stephanie R.
Verified Background Check
Stephanie R.
from
$35
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Oxford, MD, 21654

About: Loving family for your furry friend. Walks and tummy rubs. We are located in the perfect walkabout town with beaches, dog park, and open spaces. Know that your furry family member will be well cared for in our home. Last minute or scheduled in advance. We accept them big and small. We just lost our beloved Zoey, our little shichon. If your pet prefers to chill alone there is plenty of room for everyone to have their own space. Stop by today for a meet and greet. We are a small family. We at the periwinkle bungalow in Oxford are at your service to make your life on the shore swell! I work from home. We like quiet mornings doing the crossword puzzle, usually cooking something yummy. We spend most of our time in the open kitchen living room space. Small home and pets are allowed everywhere except on my bed. Big yard and proximity to everything in a very quaint little town by the water. Our cats live upstairs on their own floor when we have guests, so no worries.

Sitter Profile Image: Lindsey B.
Verified Enhanced Background Check
Lindsey B.
from
$15
per walk
5.0 out of 5 stars
2 reviews
10 years of experience
Cordova, MD, 21625

About: I’ve taken care of all types of animals since I started high school. I grew up with dogs, cats and poultry and those are the animals I’ve taken care of most. I’m comfortable with senior care for sure but young puppies and extremely young kittens are outside of my comfort zone. I’m currently commuting to SU for this last semester and finishing off a major doesn’t allow for a lot of job opportunities that were available previously due to the amount of at-home work required. Pet sitting allows a lot more flexibility and brings the brain break of hanging out with fur babies to fit into the class work chaos. I currently have a cat of my own who stays with me as well as my childhood cat and dog who live with my parents. I’ve often pet sat for family and am comfortable with all ages except young puppies and very young kittens.

Sitter Profile Image: Hunter G.
Verified Enhanced Background Check
Hunter G.
from
$15
per walk
4 years of experience
Cambridge, MD, 21613

About: I enjoy walking at least once a day so why not bring your pets along with me ? I enjoy doing it so you know the job will get done correctly and I have a flexible schedule so I’m down to walk whenever I can I’m available normally early mornings, or evening if I am busy it’s because I’m at my restaurant job but I am more than willing to work with whatever schedule a client has ! I do have a cat myself but I don’t really see a reason to have someone else’s pet inside my own home, I am happy to pick up any droppings, refill water bowls and tidy up inside of someone else’s home when I am picking up a clients pet!

Sitter Profile Image: Rebekah L.
Verified Background Check
Rebekah L.
from
$33
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
9 years of experience
Trappe, MD, 21673

About: Not only do I just genuinely love dogs, I also have prior experience working with dogs at a doggy day care and veterinary hospitals. I’ve dealt with dogs from 5lbs-150+lbs. I have experience with diabetic dogs, blind dogs, seizure dogs, etc. I am capable of anything you need me to do for your furry kids! From giving them medication at certain times, to feeding them a specific diet, anything they need. I will love on them while you are away and give them all of the attention they need, as well as updating you with cute pictures! As always, I am only a text or phone call away. If for any reason, they have a medical emergency, I will call you right away and take them to your vet. If they have any grooming or vet appointments that you need me to take them to or pick them up from, I offer those type of services too. Any questions you have, please feel free to ask and we can surely discuss options that suit you and your babies best! I can’t wait to meet and learn everything I need in order to provide the best care for your furry kids!!!! I work at a vet clinic currently so throughout the day I am taking care of many peoples pets and fur babies. Whenever I’m dog sitting, I try my hardest to be there for other peoples pets whenever they are away as I treat everyone’s pet as if they were my own. Every pet deserves love and care. I try my hardest to provide clear communication with myself and the owners of the pets I sit for. I would expect nothing less then detailed communication as well as pictures so that my clients trust that their pets are in great care while they are away.

Sitter Profile Image: Bridget M.
Verified Enhanced Background Check
Bridget M.
from
$20
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
15 years of experience
McDaniel, MD, 21647

Ruby came back so sleepy! Exactly what I want from an hour walk. Bridget asks good questions and gives you updates about how your dog is doing. She is very aware of her surroundings and making sure Ruby is able to have her best walk. Ruby is afraid of cars and kids- I heard Bridget praise and redirect Ruby when encountering a scary thing. She really cares about my dog and it is noticeable. 10/10- highly recommend!

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Rose C.
Sitter Profile Image: Christie R.
Verified Enhanced Background Check
Christie R.
from
$40
per walk
4.9 out of 5 stars
30 reviews
16 repeat clients
10 years of experience
Church creek, MD, 21622

Christie was excellent! She arrived on time, provided all the requested services, and gave good notes on their time together. I appreciated the thorough account of the care she provided during her visit for my pup’s walk and the pictures!

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Tina M.
Sitter Profile Image: Rachael B.
Verified Enhanced Background Check
Rachael B.
from
$25
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Queen anne, MD, 21657

About: I have 7 animals of my own, both dogs and cats. I also work part time as a Kennel Technician so I am very familiar with different animal personalities and how I’m expected to care for them! Neighbors, friends, family & clients have relied on me to care for their furry friends and I’ve loved getting to know each one. I am pet CPR & First aid Certified. I walk for 3-4 houses around noon Monday- Friday as well as dog sitting overnights frequently. I am very flexible and will not have to spend long periods of time away from your pets. I work part time as a kennel tech and attend college. College is online so that won’t be a problem right now. My scheduled days can change but shifts are no longer than 6 hours at a time. I usually work every other day. I live in Queen Anne so I’m about the same distance to everyone. I have a few clients that I walk dogs for during the afternoon and am always on time! I will take wonderful care of your pets as if they were my own. My pups love to play outside and get lots of attention so I want to share the love!! It’s always fun getting to know your dogs and cats. I have built a trusted clientele over the last 2 years of being on Rover. I am very responsible and will care for your house just as well as your pets! I know it takes a lot to entrust someone in your home so I won’t let you regret it.

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The median cost per walk for dog walking in Windyhill is $20

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Sitters in Windyhill average 2
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Windyhill on Rover as of Jun 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Windyhill dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 160 dog walkers in Windyhill. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 77% of Windyhill dog walkers respond in under an hour.

Dog walkers in Windyhill have an average of 19 years of experience. Dog walkers with repeat customers have an average of 2 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Windyhill.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 160 dog walkers in Windyhill on Rover, so you’re sure to find the perfect match for your dog! In Windyhill, 92% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.