Dog Walking In Hillside

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

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Hillside dog walkers

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

1 / 1
Sitter Profile Image: Riley L.
Verified Enhanced Background Check
Riley L.
from
$16
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
3 years of experience
Avenues West, Milwaukee, WI, 53233

Riley was wonderful with Rocky! It was great to receive pictures from their walks each day. I’d definitely recommend her to anyone looking for a reliable walker :)

Profile image
Emily D.
Sitter Profile Image: Jackie C.
Verified Enhanced Background Check
Jackie C.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
145 reviews
50 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Nothing but great things to say about Jackie! She was able to walk Jenko on a last minute request. Have used her on multiple occasions since. Great communication and follow up. Definitely recommended her for any dog walking needs

Profile image
Steven C.
Sitter Profile Image: Ixzel R.
Verified Enhanced Background Check
Ixzel R.
from
$14
per walk
7 years of experience
Milwaukee, WI, 53212

About: What sets me apart is both my personal and professional experience caring for animals of all ages, sizes, and personalities. I’ve grown up around dogs my entire life and currently work at Dogtopia, where I care for and supervise dogs daily. This has helped me become patient, attentive, and comfortable working with different temperaments and energy levels. I also have experience with both senior dogs and puppies. My senior dog, Otis, had arthritis, so I learned how important patience, comfort, and attentive care are for older pets. I also helped raise and train our pug puppy with basic training, routines, and socialization. Because of these experiences, I understand that every pet has different needs depending on their age and personality, and I always try to make pets feel safe, active, and cared for like they’re my own.⭐️😊 Pet care is already a big part of my daily routine. I work at Dogtopia, where I help maintain a safe, clean, and fun environment for dogs of all sizes and personalities. 🐾 My job has taught me the importance of paying close attention to dogs’ behavior, safety, and overall well-being throughout the day. When I’m home, I also spend a lot of time caring for my own dog. I enjoy taking him on long walks by the lake, staying active with him through runs and playtime, and making sure he gets plenty of attention, exercise, and care every day.🦮🏃‍♀️❤️ When caring for pets in my home or a client’s home, I always prioritize safety, comfort, and keeping pets on their normal routine as much as possible. I make sure the environment is clean and secure by checking doors, gates, food, and anything that could be unsafe or easily gotten into by curious pets.🤗 I also pay close attention to each pet’s behavior, energy level, and individual needs to help them feel comfortable and stress-free while their owner is away. Whether it’s feeding, walks, playtime, medication reminders, or simply giving them attention and companionship, I always try to make pets feel safe, cared for, and at home.

Sitter Profile Image: Alexandra I.
Verified Enhanced Background Check
Alexandra I.
from
$16
per walk
5.0 out of 5 stars
11 reviews
1 repeat client
10 years of experience
Juneau Town, Milwaukee, WI, 53202

About: I've grown up around animals my whole life, including horses, dogs, cats, birds, even miniature donkeys of all ages, and I've never gone a day with less than 8 pets! In addition to owning several loving pets, my mom and I have rescued many pets from unsafe situations and helped nurse them back to a healthy condition, which has given me experience with animals of all personalities, backgrounds, and needs. I've cared for dogs my entire life, and have experience caring for up to 5 dogs at once. I am very comfortable handling both high energy and more relaxed dogs, and I adjust my care to fit each dog's individual needs. My responsibilities have included feeding, walking, supervising playtime, bathtime, dispensing oral medication, and making sure each dog stays safe, happy, and well cared for. Back home with my parents, I have two loving dogs - Millie who is a highly energetic dog who can't get enough playtime and Fletch who just wants love and affection 24/7. Caring for them has given me experience understanding different temperments. I also have experience overnight pet sitting for a dog and cat simultaneously while also baby sitting three children all with different schedules as well as daily check ins on a farm which included caring for several dogs, cats, horses, rabbits, and birds, so I am very reliable and comfortable managing multiple tasks at once while maintaining routines and giving attention and exercise as needed. I treat every pet like my own and make sure they feel safe, comfortable, and well cared for while their owners are away. I am currently available full time every day of the week/weekend through August 31, 2026. My schedule may change, but I will make sure to update my profile if that is the case! I provide care in the client's home to keep pets comfortable in their familiar environment and maintain their normal routine. During daily check ins, I make sure pets are fed, have fresh water, and recieve attention, playtime, or walks depending on their needs. I also handle litter box cleaning for cats and any basic household care related to the pets. For overnight stays, I stay in the home to provide consistent care, companionship, and supervision throughout the day and night. I am very detail-oriented and follow instructions closely, maintaining feeding and exercising schedules and make sure pets feel safe, relaxed, and cared for while their owners are away. I also pay attention to each pet's individual personality and adjust my care to fit their comfort level, whether they are energetic and playful or more shy and independent. In addition to in house pet care, I have no trouble taking pets for walks outside of the area whether that is a dog park, around the neighborhood, or by the lake per owner request. I also have a dog park at my apartment complex and would be willing to take pets to a coffee shop for a pup cup if that is of the owner's interest! My top priority is to keep pets safe, healthy, and stress free by maintaining their routine and giving them reliable, attentive care.

Sitter Profile Image: Jessica B.
Verified Enhanced Background Check
Jessica B.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
16 reviews
9 repeat clients
16 years of experience
Milwaukee, WI, 53206

Jessica is amazing! Our dog Gabby stayed with her during the day and they got to enjoy nice walks, go to the park and get lots of play time. Jessica kept us updated during the day and sent us lots of cute pictures. Gabby is excited to see her again!

Profile image
Chadwick and Mayara M.
Sitter Profile Image: Jamie S.
Verified Background Check
Jamie S.
from
$14
per walk
5.0 out of 5 stars
28 reviews
13 repeat clients
17 years of experience
Avenues West, Milwaukee, WI, 53233

Thanks again Jamie! Augie enjoyed his walk. We appreciate your help.

Profile image
Gabriel S.
Sitter Profile Image: Mikalanne T.
Verified Enhanced Background Check
Mikalanne T.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
51 reviews
16 repeat clients
4 years of experience
Riverwest, Milwaukee, WI, 53212

Mika is great! They are incredibly caring and good with my dog. They have helped tremendously with his loose leash walking while making sure he gets lots of energy out. My dog loves them!

Profile image
Irene S.
Sitter Profile Image: Jake R.
Verified Background Check
Jake R.
from
$20
per walk
5.0 out of 5 stars
13 reviews
3 repeat clients
10 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Jake has been fabulous with my dog— he clearly has a great energy with animals and his dog Atlas has been a major bonus as Hanu loves playing chase with him. Additionally, he’s prompt and professional with his replies and shares some adorable photos. Would definitely recommend for anyone looking for a walker!

Profile image
Alison L.
Sitter Profile Image: Nina W.
Verified Enhanced Background Check
Nina W.
from
$16
per walk
10 years of experience
Avenues West, Milwaukee, WI, 53233

About: I provide dependable, attentive care and treat every pet like they are my own. I understand that every animal has different needs and personalities, so I take the time to make pets feel comfortable, safe, and loved while their owners are away. I’m patient with shy or anxious pets, energetic with playful dogs, and gentle with senior animals who may need extra support and slower-paced care. I’m also very detail-oriented and make sure routines are followed closely, including feeding schedules, medications, walks, potty breaks, and playtime. I communicate consistently with pet owners through updates and photos so they always know their pet is happy and well cared for. What sets me apart most is the amount of genuine attention and affection I give to each pet. I don’t just “watch” animals — I spend quality time with them to make sure they feel comfortable, engaged, and cared for while you’re away. I'm currently nannying on weekdays from 8:00am - 4:30 pm, so I’m available for morning visits before work, evening walks/check-ins, and overnight care depending on the pet’s needs. I’m especially flexible on weekends and have much more availability for walks, drop-ins, extended stays, and quality playtime. When caring for pets in a client’s home, I focus on keeping their routine consistent, stress-free, and fun. I make sure pets are fed on schedule, get plenty of exercise, attention, and playtime, and feel comfortable while their owners are away. I have experience with dogs of all sizes. I have two large-breed dogs at home, so I’m comfortable handling bigger, high-energy dogs, and I have also frequently dog sat for smaller-breed dogs with different temperaments and care needs. I’m reliable, detail-oriented, and always follow owner instructions closely, including feeding schedules, walks, medications, and any special care requests.

Sitter Profile Image: Elise D.
Verified Enhanced Background Check
Elise D.
from
$14
per walk
5.0 out of 5 stars
7 reviews
3 repeat clients
25 years of experience
Riverwest, Milwaukee, WI, 53212

Elise walks my dog twice a week, and it’s been a fantastic experience. She is friendly, reliable, and genuinely loves dogs. My dog took to her right away and looks forward to her visits. I also appreciate the reports, pictures, and consistency—she go above and beyond. Highly recommend to anyone looking for dog walker! Highly recommend to anyone looking for a trustworthy and kind dog walker!

Profile image
Suzanne G.
Sitter Profile Image: Kayla A.
Verified Background Check
Kayla A.
from
$25
per walk
5.0 out of 5 stars
71 reviews
28 repeat clients
23 years of experience
Lower East Side, Milwaukee, WI, 53202

My puppy girl is always so excited to see Kayla for her walks! Kayla is great! She is an excellent communicator and has been reliable. I can tell she is good with my puppy based on how long they are able to walk for and the sweet pictures Kayla sends of her. Seriously the best dog photographer out there which is an added perk ;)

Profile image
Chalani E.
Sitter Profile Image: Maggie S.
Verified Enhanced Background Check
Maggie S.
from
$16
per walk
5.0 out of 5 stars
15 reviews
3 repeat clients
10 years of experience
Riverwest, Milwaukee, WI, 53212

Met with Maggie for a meet and greet and a walk. Maggie was very responsive and prompt. She was communicative in the app, providing pictures and updates on their potty breaks as well. I’m looking forward to working with her again.

Profile image
Jasmine S.
Sitter Profile Image: Madeline R.
Verified Enhanced Background Check
Madeline R.
from
$15
per walk
11 years of experience
Lower East Side, Milwaukee, WI, 53202

About: I love nurturing all living things from children (although I am not yet a parent to a human), to plants and animals alike! I tend to put all living things before my own needs to prioritize their well-being. In addition, I recently took in a crested gecko and have learned so much about caring for reptiles as well. Everyday before leaving my apartment I make sure that both of my pets have plenty of food and water. In addition, I check to ensure that my plants are out of reach from my cat and that my bioactive terrarium is maintaining humidity. I care for pets by making sure they have food, water, a clean liter box, a moist environment, and get taken out for potty breaks depending on which animal I am caring for. I am willing to care for your pets with the same considerations in mind.

Sitter Profile Image: Travis H.
Verified Background Check
Travis H.
from
$30
per walk
5.0 out of 5 stars
343 reviews
107 repeat clients
35 years of experience
Riverwest, Milwaukee, WI, 53212

Travis did a very good job walking my dog Mikah while I was away. He is very friendly and my dog warmed up to him instantly. He was very persistent with the report cards and sending photos. Definitely would work with him again and recommend!

Profile image
Shari S.
Sitter Profile Image: Addison S.
Verified Enhanced Background Check
Addison S.
from
$15
per walk
10 years of experience
Lower East Side, Milwaukee, WI, 53202

About: For the past 10 years, I’ve cared for neighbors’ and friends’ dogs—often for long stretches while they’re away—so I’ve worked with a variety of breeds and personalities. I grew up around dogs and currently have pets of my own, so I’m comfortable with daily routines, walks, feeding schedules, and giving plenty of exercise and playtime. Whether a dog is energetic, shy, or extra cuddly, I make sure they feel safe, loved, and entertained. I stick closely to owner instructions, keep things clean, and treat every dog like part of the family. Pet care fits easily into my routine because I work from home and have flexible hours. I can accommodate regular check-ins, feeding schedules, walks, and playtime throughout the day. I have my own transportation, so getting to and from clients’ homes is never an issue. I’m reliable, consistent, and able to adapt to each pet’s daily needs. Whether I’m caring for pets in my home or a client’s home, safety and comfort come first. I follow all owner instructions closely, keep routines consistent, and make sure pets are always secure—whether that means proper leash use, safe outdoor time, or monitoring food and water. In a client’s home, I treat the space with respect and leave things clean and organized. If pets are in my home, they get a calm, loving environment with plenty of attention, play, and rest. I always communicate clearly, send updates, and make sure owners feel confident their pets are in good hands.

Sitter Profile Image: Raina T.
Verified Enhanced Background Check
Raina T.
from
$15
per walk
1 repeat client
1 year of experience
Harbor View, Milwaukee, WI, 53201

About: I grew up with both dogs and cats. I currently have two cats of my own that I love with my entire heart! I know what it’s like to have pet parent guilt leaving your fur babies alone at home, and I would love to help take that weight off your heart! I am a professional volleyball player. I live here in Milwaukee during the off-season and don't have much to do in the summer. I workout in the mornings at 9am, but after that I am completely free. My gym is out in Wauwatosa, so it is no problem for me to make a trip out to the suburbs every day! I am usually busy on weekends, but weekdays are almost always wide open! I will follow whatever plan/schedule that you have laid out for your fur babies! I would feel most comfortable walking and caring for dogs that are trained on leash!

Sitter Profile Image: Aubrey A.
Verified Enhanced Background Check
Aubrey A.
from
$20
per walk
5.0 out of 5 stars
64 reviews
18 repeat clients
27 years of experience
Lower East Side, Milwaukee, WI, 53202

Aubrey did a great job communicating when she had issues getting into our apartment. She was able to get in and let Sunny out to go potty which is exactly what we needed!

Profile image
Blake H.
Sitter Profile Image: Melissa A.
Verified Enhanced Background Check
Melissa A.
from
$18
per walk
5.0 out of 5 stars
22 reviews
9 repeat clients
12 years of experience
Northpoint, Milwaukee, WI, 53202

Melissa did a great job watching my dog while I was out of town. She was prompt, reliable, communicative, and I'd definitely ask Melissa to watch him again!

Profile image
Sarah H.
Sitter Profile Image: Jessica K.
Verified Enhanced Background Check
Jessica K.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
39 reviews
11 repeat clients
15 years of experience
Northpoint, Milwaukee, WI, 53211

Jessica took the best care of Max! Her communication was impeccable and you could see the quality in her care she provided for our dog. We could tell Max looked forward to his walks with her. We would highly recommend her care with anyone’s pet!

Profile image
Abigail B.
Sitter Profile Image: Janneke C.
Verified Enhanced Background Check
Janneke C.
from
$15
per walk
15 years of experience
Kilbourn Town, Milwaukee, WI, 53205

About: I have taken care of animals since I was in middle school! I have cared for all types of dogs, from lap dogs to Irish Wolfhounds! I have also cared for all ages of cats! I am an animal lover who has a 7 year old Dachshund named Finn, who I have raised since he was a puppy! I currently have a full time office job but am free after work and on weekends! I also work from home on Friday's and can come during the day on those days! I will treat your pet like my own and always do my best! Let me know any special care or peculiarities and I will accommodate!

1 / 1
View more sitters

Hillside dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Great things to say about Riley! Will definitely use her again. Very professional and timely and was great with my dog!

Profile image
Alayna H.
Dog Walking
5.0 out of 5 stars

Jessica is great! On time every day and very communicative with any changes. She was understanding of any modifications we needed to make with days or times and our Mona looked forward to seeing her!

Profile image
Amanda G.
Dog Walking
5.0 out of 5 stars

This is the third time we have had Emily come help take care of our dog and I have nothing but great things to share. She is always on time, sends great pictures, but most importantly I know that she is attentive to our dog and her needs. For example, a few weeks ago, Emily watched our dog for a weekend when we were out of town. At that time, I gave instructions to let the dog out in the backyard before going on the first walk of the day because our dog always has a few zoomies first thing in the morning and it will make the walk smoother. When she came to do an AM walk this time, she remembered about the zoomies and let our dog out back for a few minutes before heading out. I hadn’t remembered to remind Emily of that, so it felt great knowing that she took initiative and catered to our dog’s specific habits/needs. Additionally, I had a neighbor share (unprompted) that they noticed how wonderful the interactions were between Emily and our dog. They said that they heard Emily talking to our dog when they were together and really focused on her, not just going through the movements of taking a dog for a walk. I will continue to book Emily and can confidently recommend her.

Profile image
Sabrina C.
Dog Walking
5.0 out of 5 stars

Jessica takes my high energy puppy on good long walks. She makes an effort to get her clean before heading out too which is appreciated.

Profile image
Andi G.
Dog Walking
5.0 out of 5 stars

Carole was a great communicator, took wonderful care of Monte and sent us a pic and follow/up. We’d rely on her again in a heartbeat!

Profile image
Shacey P.
Dog Walking
5.0 out of 5 stars

Carrianne helped us out with a last minute walk for our dog, Otto. We appreciate the photos. It looks like he had a great time!

Profile image
Elizabeth S.
Dog Walking
5.0 out of 5 stars

Travis is very easy to communicate with and very flexible as well! We appreciate him being available so last minute for us and our dog had a great time with him!

Profile image
Kinga P.
Dog Walking
5.0 out of 5 stars

Met with Maggie for a meet and greet and a walk. Maggie was very responsive and prompt. She was communicative in the app, providing pictures and updates on their potty breaks as well. I’m looking forward to working with her again.

Profile image
Jasmine S.
Dog Walking
5.0 out of 5 stars

Jackie was extremely attentive and great with our Daisy! Our dog warmed up to Jackie right away, and thoroughly enjoyed the walk with her. We are looking forward to many more!

Profile image
Nina S.
Dog Walking
5.0 out of 5 stars

Isabella is a prompt and efficient dog walker. My pup was excited to see me when returning home from work and I was excited that my apartment showed no signs that he was stressed or anxious since he saw a friend midday!

Profile image
Noah S.
Dog Walking
5.0 out of 5 stars

I have had my sweet little dog for over 15 years. No one has walked her except for family members and the people at doggy daycare. She is also deaf and partially blind. So I was extremely nervous to have somebody else walk her. But this was perfect! Leandrea did a great job with Jolie! She was on time, didn’t mind Jolie dragging her around the condo building several times, and give her kisses. It was wonderful to hear and to see Jolie happy and excited in all the pictures.

Profile image
Melissa S.
Dog Walking
5.0 out of 5 stars

Jessica is fantastic! She is on time, gives my dogs a good walk and excellent care and is 100% reliable. She notifies me if something out of the ordinary happened (like my dog counter surfing and eating a pie!) and even brought in a package that was left by my door. I’m so glad we found her.

Profile image
Amy N.
Dog Walking
5.0 out of 5 stars

Hope is so great! Very good with communication and helping out with all the details. Highly recommend

Profile image
Benji M.
Dog Walking
5.0 out of 5 stars

Samuel did a wonderful job making sure my puppy was able to exercise and let loose during my long day at work. He was easy to communicate with and was reliable when obstacles came up during my dog’s first walk!

Profile image
Noah S.
Dog Walking
5.0 out of 5 stars

Steven was fantastic! As a first-time dog owner, I’ve never left my puppy alone or with anyone else until now, so this was a big step for me. I’m so grateful to have found someone I (and Moose!) trust and feel comfortable with. He took great care of Moose, and it definitely showed - Moose is happy and completely worn out after the day. Thank you for taking such good care of him!

Profile image
Gillian H.
Dog Walking
5.0 out of 5 stars

Elise walks my dog twice a week, and it’s been a fantastic experience. She is friendly, reliable, and genuinely loves dogs. My dog took to her right away and looks forward to her visits. I also appreciate the reports, pictures, and consistency—she go above and beyond. Highly recommend to anyone looking for dog walker! Highly recommend to anyone looking for a trustworthy and kind dog walker!

Profile image
Suzanne G.
Dog Walking
5.0 out of 5 stars

The dogs like him and he can handle the dogs! Very polite and very reasonable when I asked about changing the schedule. Much appreciated!

Profile image
Amber J.
Dog Walking
5.0 out of 5 stars

Is great with Strummer and has been quick to respond with any questions I have had and updating with pictures and feedback after walking Strummer.

Profile image
Eric A.
Dog Walking
5.0 out of 5 stars

Aubrey has been my recurring dog walker. She’s great!! I know my dog is safe with her and she is easy to communicate with. Highly recommend!

Profile image
Emily L.
Dog Walking
5.0 out of 5 stars

Best dog walker we have ever had. Ashley was amazing with Rhubarb and always sent the best pictures and walk notes. Will be looking to hire her again in the future!

Profile image
Jackson R.
Dog Walking
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a dog walker who’s a great match for you and your dog
  2. 2. Meet & Greet

    Meet either virtually or in-person with a walker to discuss the level of care needed for your dog
  3. 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!

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.

Dog Walking FAQs

Frequently asked questions about Rover

If you’re searching for a Hillside 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.

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

Experience can vary widely from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when comparing dog walkers available in Hillside.

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

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.