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.
“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 🐕”

“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.”

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.

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 🫵🏾🙂↕️

“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.”


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!
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!

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.
“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! ”

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.

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
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.
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.
“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!”

“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.”

“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!”


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.
“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!”

Over 19 pet parents in Winsor Hills have booked dog walking
Winsor Hills dog parents share their Rover experiences
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 🐶❤️
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!

How Rover works

1. Search
Read verified reviews and choose a dog walker who’s a great match for you and your dog
2. Meet & Greet
Meet either virtually or in-person with a walker to discuss the level of care needed for your dog
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per walk for dog walking in Winsor Hills is $20
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog walker has to cancel, we’ll work with you to find a new walker.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
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.
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.












