Dog Walking In Winsor Hills

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

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Top rated Winsor Hills 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: Sophie C.
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Sophie C.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
94 reviews
23 repeat clients
9 years of experience
Wakefield, Baltimore, MD, 21207

Sophie did an amazing job with my dogs per usual and I know they gave her more trouble than they would give me. I'm forever grateful for her and trust her to care for my dogs 🐕

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Diamond D.
Sitter Profile Image: Nautica E.
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Nautica E.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
50 reviews
13 repeat clients
11 years of experience
Forest Park, BALTIMORE, MD, 21216

Nautica was on time and pleasant. She walked my dogs and gave them a good walk to get their energy out. I will be using her again.

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Lakeyva S.
Sitter Profile Image: Cashae H.
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Cashae H.
Star Sitter
from
$21
per walk
5.0 out of 5 stars
10 reviews
4 repeat clients
2 years of experience
Hunting Ridge, Baltimore, MD, 21229

Milo can be a bit tempermental and a little over protective, Cashae's calm and serene aura has attributed to Milo being able to trust her and like his walks with her. I have tried other walkers in the past but they never worked out. Hooray for Cashae!!! She is also very polite and very punctual. I feel so blessed to have her.

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Linda
Sitter Profile Image: Iman K.
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Iman K.
from
$25
per walk
5.0 out of 5 stars
5 reviews
9 years of experience
Forest Park, Baltimore, MD, 21207

About: I’ve been caring for my dogs for about 9 years now, and they truly are my babies!! I currently have a Siberian Husky and a German Shepherd, and we recently added a Golden Retriever puppy to the family!! So my puppy skills are definitely fresh right now 😊 I’m very used to high energy dogs, lots of playtime, long walks, mental enrichment, cuddle sessions, and making sure every pup feels safe, happy, and loved. Whether your dog is super playful, shy, or just wants extra TLC, I’ll always treat them like one of my own. I recently graduated from UB with my bachelor's degree and am currently in the process of applying for jobs! That means I have a very flexible schedule and plenty of free time throughout the week, so I’m typically available whenever you need care. I’m happy to work around your schedule and make things as easy as possible for both you and your pup. Your pup's safety and comfort are always my number one priority. I make sure to follow your instructions exactly, whether that’s feeding routines, walks, meds, or small things that help your dog feel at ease. I’m very mindful during walks and outdoor time, always keeping dogs securely leashed and being 100% aware of our surroundings. When I’m in your home, I respect it like it’s my own space. I keep everything clean, double check doors and gates, and make sure your pup is safe and settled before I ever step out.

Sitter Profile Image: Briauna N.
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Briauna N.
from
$15
per walk
20 years of experience
Greater Rosemont, Baltimore, MD, 21216

About: I've lived with animals all my life, from dogs to cats, lizards, snakes, tortoise's and currently chickens. So fear not! Because I love all animals 🙂‍↕️ This is my main source of income since the job market isn't the best, so I'm always ready to take care of some pups and kitties Whether big or small, I'll always making sure your lil guy or gal feels comfortable, is properly fed and properly walked. And if needed, I am not opposed to bringing any external needs for your pet 🫵🏾🙂‍↕️

Sitter Profile Image: Victoria Y.
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Victoria Y.
from
$30
per walk
4.8 out of 5 stars
35 reviews
8 repeat clients
14 years of experience
Forest Park, Baltimore, MD, 21216

After I knew the Rover from another dog owner, I haven’t used. Our very senior Lab (16 years old) recently became very weak, in walking etc, unable to leave a pet hotel as we did just half years ago. During my family away, I needed to find somebody to come to my house, taking care of her, very gentle, using towel to leave to lawn etc. While working, she sent me how her walk with Jasmine attaching photos and message. I really appreciate Victoria in very nicely taking of our family dog with affection (I could feel this from her gentle messages, even though I haven’t met her at all. My wife met her for the first time then went to travel, but I didn’t cause I’m working when she comes.). This is the first time to use Rover, and not sure about other dog walker at all. Anyway, I’m satisfied the system of Rover very efficient to find a dog walke and could fine Victoria, and was very happy to have Victoria for the first time experience.

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Kazuhiro Y.
Sitter Profile Image: Julia P.
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Julia P.
from
$15
per walk
2 years of experience
Beechfielf-Irvington Area, Baltimore, MD, 21223

About: I’ve taken care of dogs for a long time as I’ve had many dogs myself throughout my life! I love animals so much!! I work at a school full time from the end of August until the beginning of June. I will be available full time during the summer Monday-Friday all day! I have a fenced yard where your pupper will be able to walk around freely! I will also take them for walks around the neighborhood and to the park! I am willing to travel to you as well! My senior dog recently passed away and would love company!

Sitter Profile Image: Shakiyla H.
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Shakiyla H.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
27 reviews
11 repeat clients
10 years of experience
Park Heights, Baltimore, MD, 21215

About: I specialize in caring for large breeds, leveraging years of experience raising and training Rottweilers. I understand the unique needs of big dogs, from maintaining consistent training to managing their energy levels. Note: I have my own crated pets who will be present. Pet care is part of my everyday life. I work from home so I have a lot of flexibility! My own Rottweilers are on a consistent schedule, so it’s natural for me to fold guest pets right into that routine. Each day includes morning walks, feeding, supervised play, and crate rotations for safety, along with plenty of affection and downtime. I make safety, trust, and comfort the focus of every stay. In my home, pets enjoy a secure, spacious environment with constant supervision, plenty of enrichment, and clean, cozy areas for rest and play. Whether calm and quiet or high energy and active, your pet will be safe and secure with me!

Sitter Profile Image: Kelly C.
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Kelly C.
from
$30
per walk
4.8 out of 5 stars
110 reviews
49 repeat clients
15 years of experience
Greater Rosemont, baltimore, MD, 21216

Kelly was great! She was really responsive and took such great care of Bella. We will definitely hire her again!

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Susanne C.
Sitter Profile Image: Danielle H.
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Danielle H.
from
$17
per walk
10 years of experience
Howard Park, Baltimore, MD, 21207

About: I have taken care of two smaller dogs the past 3 years and have learned the hard work that comes with them. I have also volunteered at BARCS for dog days out. I am comfortable with leash trained dogs and understand feeding schedules, potty breaks, and playtime. Hello! I am currently a college student working a part-time internship and taking a summer class! I am often available on weekends and monday, wednesday, and friday nights. I know how to crate dogs if needed and have reliable transportation to an emergency vet if needed. I have grown up around cats and dogs all my life so I understand the importance of keeping your pet safe.

Sitter Profile Image: Janine J.
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Janine J.
Star Sitter
from
$30
per walk
4.9 out of 5 stars
456 reviews
227 repeat clients
4 years of experience
Woodlawn, MD, 21207

J is awesome! We're so happy we found her! She is super friendly and dependable and also patient (as i had a few regrettable spare key situations. She is also has super warm and good energy! Thanks for taking such good care of Ripley!

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Joseph I.
Sitter Profile Image: Grace M.
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Grace M.
from
$16
per walk
5.0 out of 5 stars
7 reviews
3 repeat clients
18 years of experience
Hampden-Woodberry-Remington, Baltimore, MD, 21211

About: Hi there! I’ve been caring for pets, be it my own or others, most of my life and it is one of those things in my life that fulfills me. I am a graduate student at JHU and this is my side hustle lol! I’m currently working part time and starting school in the fall, so i have those time commitments to work around, but i always have time for your animals:) Making sure that the animals I care for are fed and have water is important to me. Making sure that the animals I care for are given time to walk and play and feel loved is what I love about taking care of them.

Sitter Profile Image: Melissa A.
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Melissa A.
from
$15
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
5 years of experience
Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21217

About: Experienced pet sitter caring for dogs and cats, including my grand kitties at home, providing feeding, playtime, litter care, and a calm, loving, consistent environment daily Pet sitting fits naturally into my routine, with scheduled walks, feeding, playtime, and check-ins, ensuring pets receive consistent care, attention, and comfort every day I create a safe, calm space by following routines, monitoring behavior, securing surroundings, using gentle handling, and building trust through patience, consistency, and positive interactions daily

Sitter Profile Image: Jayden M.
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Jayden M.
from
$14
per walk
5.0 out of 5 stars
4 reviews
3 repeat clients
5 years of experience
Roland Parl-Homewood-Guilford, Baltimore, MD, 21211

About: I’ve had pets all of my life (18 years) and I’ve learned that I love animals and taking care of them just comes easy to me. I would love to watch and take care of dogs. I will treat your pet like it’s one of my own. I’m currently in the process of finding a new job so I will be free everyday of the week until then! If I could make dog walking/sitting my main job, I would love to do that! I handle pets with care and respect. I never want to hurt an animal. I will do whatever the pet owner needs me to do with no problem.

Sitter Profile Image: Emily T.
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Emily T.
from
$30
per walk
5.0 out of 5 stars
37 reviews
11 repeat clients
15 years of experience
Greater Rosemont, Baltimore, MD, 21216

About: As an experienced pet sitter in both the Bay Area and Baltimore, I am be the perfect person to care for your pet! I’ve sat for many dogs of varying breeds, temperaments, and ages, and can be very flexible with my schedule as I work remotely full-time. Growing up in a big family, I have a lot of experience with pets and children. Over the course of my lifetime, my family has owned 4 dogs and 2 cats. I now have 2 dogs of my own, and know just how important it is to have quality care for your pets. I am honest, trustworthy, dependable, and caring - perfect for watching your dogs while you are away! I work from home and have a flexible schedule, which allows me to take great care of your dogs! I can usually accommodate 3 drop-ins per day. I will be sure to follow all house rules and guidelines, and I have experience with a wide variety of dog breeds. My two dogs are very high energy, and I am experienced in calming them down. If I am house-sitting for you, I do not need to bring my dogs - my husband will watch our dogs in our home.

Sitter Profile Image: Kevin D.
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Kevin D.
from
$25
per walk
5.0 out of 5 stars
11 reviews
7 repeat clients
25 years of experience
Greater Rosemont, Baltimore, MD, 21216

Kevin walked Charlie every evening while we were away for a week. She is dog reactive and Kevin was comfortables and competent and handing this issue. Thanks Kevin!

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Nisshani P.
Sitter Profile Image: Jahborne D.
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Jahborne D.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
92 reviews
13 repeat clients
7 years of experience
Catonsville, MD, 21228

He is wonderful! My dog loves him. He does a great job of being friendly and sweet with my animals but also keeps him in-line! He doesn't let him pull or run all over the place! He's also very respectful of my house and towards myself.

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Ashley B.
Sitter Profile Image: Susan M.
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Susan M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
10 reviews
27 repeat clients
3 years of experience
Catonsville, MD, 21228

Susan was a BLESSING for me and my dog when we needed a last minute check-in. She was so incredibly thorough and took great care to make sure she fit our routine and connected with Birdy. I recommend Susan to absolutely anyone who’s looking for competent care, a bubbly personality, and patience with an energetic and home-defending fuzz butt!!! We loved her!

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Allison T.
Sitter Profile Image: Bob D.
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Bob D.
from
$15
per walk
5.0 out of 5 stars
13 reviews
2 repeat clients
8 years of experience
Roland Parl-Homewood-Guilford, Baltimore, MD, 21210

About: My name is Bob, and I have been a dog owner for over 8 years, currently owning two energetic pups, Ellie and Watson! My wife works from home, so someone is almost always home, unless we all go ot in the evening! Our kids are 12 and over, and we all love spending time not only with our dogs(and cats!), but meeting new ones as well. Our rescue dogs, Ellie(18 month old female Australian Shepherd/Catahoula) and Watson(1 year old male Schnauzer/Terrier) enjoy spending time playing in the yard together when weather is nice, or horsing around together inside. They love socializing and playing at the dog park too, so having a 'play date' would be good fun for them! We have free access to water at all times, toys to play with, and healthy treats, if allowed by visiting pets' owners. Feedings for our dogs happen twice a day at 8 am and 5 pm; arrangements could be made regarding your pet's feeding needs, depending on time of day, and length of stay. Walks, playing, and lots of attention guaranteed! We can be flexible to meet your needs; please ask.

Sitter Profile Image: Samantha E.
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Samantha E.
from
$18
per walk
5.0 out of 5 stars
58 reviews
15 repeat clients
16 years of experience
Catonsville, MD, 21228

Samantha hooked me up last minute when we started an unexpected event and needed immediate recurring care. She's polite and responsive, and knows how to handle a weird finicky dog. My dog seems to love her!

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Rose C.
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Over 19
pet parents in Winsor Hills have booked dog walking

Winsor Hills dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Corinne is easy to work with. Great communicator. Great with our dog Einstein and he really loves her.

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Javier M.
Dog Walking
5.0 out of 5 stars

Jules is very professional, prompt and nice. My dog Boogs loves going on walks with Jules. Thank you.

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Birtena N.
Dog Walking
5.0 out of 5 stars

Sophie did an amazing job with my dogs per usual and I know they gave her more trouble than they would give me. I'm forever grateful for her and trust her to care for my dogs 🐕

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Diamond D.
Dog Walking
5.0 out of 5 stars

Kelly did a great job looking after our dog while we were out of town. This is our second time booking with her she’s responsive and makes sure I get pictures and videos while we are away.

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Immanuel V.
Dog Walking
5.0 out of 5 stars

I can't say enough about Ron! I'm not a morning person and neither is my pup. Ron takes great care of her and I feel entirely less hectic in the mornings. He's super easy to work with, my pup adores him, and he's communicative as well as reliable.

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Lance L.
Dog Walking
5.0 out of 5 stars

Sean is Sony’s BFF!! He is courteous and attentive to your dog’s needs and personality. I strongly reccommend Sean.

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Carole T.
Dog Walking
5.0 out of 5 stars

Ashley is amazing!! She’s consistent, flexible, professional, and super good with my rescue dog. Highly recommend!

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Alexis P.
Dog Walking
5.0 out of 5 stars

Laura has walked my dog 4 days a week for the past 2.5 years. She’s reliable and truly cares about Nora! I’d recommend her to anyone!

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Shelby C.
Dog Walking
5.0 out of 5 stars

Helen was so great and fast to pick up our last minute request while we were out of town and our scheduled walker had another emergency. Thank you thank you

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Kaytlynn M.
Dog Walking
5.0 out of 5 stars

Thank you for braving the cold for my pup! You have been so reliable and truly amazing! Thanks for all you do!

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Ashley B.
Dog Walking
5.0 out of 5 stars

Cashae is so sweet! You can tell she’s an animal lover and really cares for your pet. She’s also communicative and punctual. Feel lucky that we found her! Would definitely book Cashae again

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Bailey B.
Dog Walking
5.0 out of 5 stars

Our experience with Erika was extraordinary. She is caring, compassionate, and Egan gets excited each time she comes. Thank you for supporting our family in these challenging times and we will definitely be contacting you for our future needs and refer you to our friend group 🐶❤️

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Betty S.
Dog Walking
5.0 out of 5 stars

Erin and Michael are wonderful with my German Shepherd. I can always trust that she is in good hands when I book with Erin. Thank you!

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Dennis B.
Dog Walking
5.0 out of 5 stars

Kevin walked Charlie every evening while we were away for a week. She is dog reactive and Kevin was comfortables and competent and handing this issue. Thanks Kevin!

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Nisshani P.
Dog Walking
5.0 out of 5 stars

Miranda was prompt and very attentive to my 4 fur babies, she was able to remain calm as my babies can be a bit wild. She walked my animals and they all came in panting and ready for a nap!

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Maraina P.
Dog Walking
5.0 out of 5 stars

I never had a need to have someone else walk Greta before. She is energetic and loves to explore on hour long walks, so I had concerns about someone being able to handle her. Simon was outstanding and indulged Greta's inclinations to wander different paths around the area. I would highly recommend Simon!

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Marty S.
Dog Walking
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How Rover works

  1. 1. Search

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

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Sitters in Winsor Hills average 4
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 Winsor Hills 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 Winsor Hills 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 7,446 dog walkers in Winsor Hills. 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, 86% of Winsor Hills dog walkers respond in under an hour.

Dog walkers in Winsor Hills have an average of 14 years of experience. Dog walkers with repeat customers have an average of 4 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 Winsor Hills.

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 7,446 dog walkers in Winsor Hills on Rover, so you’re sure to find the perfect match for your dog! In Winsor Hills, 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.