Dog Walking Hillside

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

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Hillside, Find top rated dog walking

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: Alexandra I.
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Alexandra I.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
22 reviews
4 repeat clients
11 years of experience
Juneau Town, Milwaukee, WI, 53202

Alex is an excellent dog walker/caretaker. My dogs love her and she is 100% reliable. She goes out of her way to help her clients. Her communication is excellent and timely. Highly recommend.

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Amy N.
Sitter Profile Image: Mikalanne T.
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Mikalanne T.
from
$19
per walk
5.0 out of 5 stars
54 reviews
19 repeat clients
4 years of experience
Riverwest, Milwaukee, WI, 53212

Mika was amazing. They took the time to connect with my boy. My boy is hesitant about letting people getting him out of the crate and Mika was so sweet with Salvador. We will definitely be booking with them again!

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Paula O.
Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
147 reviews
54 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

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Steven C.
Sitter Profile Image: Ashley G.
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Ashley G.
from
$10
per walk
6 years of experience
Brewer's Hill, Milwaukee, WI, 53212

About: Ive always grown up having all sorts of pets, Yet because of the limited space in my apartment I can’t have as many pets as I wish right now- but i’d love to hang out, play and walks with nice doggos 🥰 I currently work a part time job in which my hours got cut back so now I have more free time and I know dog walking will be a good way to get my steps in while meeting and hanging out with fur babies🫶🏻 I have a cat and I love her to death- they are my babies and I look after them as if they were actual human babies and I’ve just felt this caring way to all animals ! 🤍🤍🐱🐶

Sitter Profile Image: Jake R.
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Jake R.
from
$20
per walk
5.0 out of 5 stars
13 reviews
4 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!

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Alison L.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
208 reviews
63 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica went above and beyond all expectations! She was great with Sullivan and even brought in a package off of our porch when she dropped sully off. Amazing walker and will definitely book again! ☺️

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Markie J.
Sitter Profile Image: Alana S.
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Alana S.
from
$20
per walk
5.0 out of 5 stars
23 reviews
6 repeat clients
5 years of experience
Lower East Side, Milwaukee, WI, 53202

Alana did an excellent job wearing out my dog! He was exhausted when he got home! I feel like she did a great job and he was safe and well looked after. I would recommend Alana to anyone!

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Lindsey W.
Sitter Profile Image: Rebecca M.
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Rebecca M.
from
$16
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

On time all the time! Very kind and professional!

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Rishi S.
Sitter Profile Image: Nina W.
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Nina W.
from
$18
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
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.
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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!

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Suzanne G.
Sitter Profile Image: Jessica B.
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Jessica B.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
16 reviews
12 repeat clients
17 years of experience
Milwaukee, WI, 53206

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!

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Amanda G.
Sitter Profile Image: Janneke C.
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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!

Sitter Profile Image: Leesa R.
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Leesa R.
from
$14
per walk
1 repeat client
10 years of experience
Juneau Town, Milwaukee, WI, 53202

About: I’ve always loved being around dogs and have hands-on experience caring for pets for family and friends. I’ve taken my brother’s dog on walks and potty breaks numerous times and understand the importance of exercise, routine, and giving dogs plenty of attention. I’ve also cared for my sister’s dog for several days at a time while she was out of town, managing feeding schedules, walks, playtime, and providing companionship. In addition, I’ve helped friends by stopping by during the day to let their dogs outside and make sure they were comfortable and cared for. I understand that every dog has a unique personality and needs, and I strive to provide patient, reliable, and loving care so both pets and owners feel at ease. Whether your dog needs a quick potty break, a fun walk, or some extra attention while you’re away, I’m committed to treating them like they’re my own. I'm currently in between jobs, so I am free any day of the week. I usually spend my mornings on my job hunt and then go for a walk or run and exercise. I'm very physically active and enjoy being outside, so I'm very open and flexible! I have a private dog park at my apartment building that is great! I am also open to whatever my clients' needs and wants are. If they need me to stay at their place for a little to help their pet feel comfortable, I can accommodate. As mentioned before, I love being outside for walks, or if you have a sporty dog that enjoys runs, I can help out as well! I have a great track record for trust worthiness and dependability. I'm very communicative and will always be available to send pictures or talk through any questions you may have.

Sitter Profile Image: Madeline R.
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Madeline R.
from
$15
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
11 years of experience
Lower East Side, Milwaukee, WI, 53202

Madeline did a great job walking my puppy Cody! Excellent communication and she followed all instructions well!

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Jessica W.
Sitter Profile Image: Casey V.
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Casey V.
from
$15
per walk
10 years of experience
Avenues West, Milwaukee, WI, 53233

About: I’ve been surrounded by animals for as long as I can remember. Growing up, my family was always fostering dogs in need of a home and spending time with them was my favorite part of the day. Family, friends, and neighbors always knew they could rely on me to watch, walk, and love their pets like my own (taking probably too many pictures of the adorable fluffers.) Because I’m currently between apartments, my schedule is incredibly open and flexible right now! I have plenty of free time during the day and week to focus entirely on your pet’s needs, routines, mid-day walks, and playtime. I care for pets in your home by adapting to the environment they are already comfortable in. Through the experience with pets of my own, I prioritize safety by double-checking locks and doors, following feeding instructions perfectly, and keeping a clean space. I make sure your pets get plenty of supervised playtime and attention, and I'll send you lots of pictures so you never have to worry about how they are doing!

Sitter Profile Image: Travis H.
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Travis H.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
355 reviews
111 repeat clients
35 years of experience
Riverwest, Milwaukee, WI, 53212

Travis is amazing with our two dogs! We feel lucky to have found him. He welcomes and follows our detailed dog care instructions. The dogs always seem happy and tired after spending time with him.

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Brent W.
Sitter Profile Image: Jessica K.
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Jessica K.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
43 reviews
12 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!

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Abigail B.
Sitter Profile Image: Maggie S.
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Maggie S.
from
$16
per walk
5.0 out of 5 stars
18 reviews
4 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.

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Jasmine S.
Sitter Profile Image: Emma G.
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Emma G.
from
$14
per walk
5.0 out of 5 stars
18 reviews
7 repeat clients
11 years of experience
Lower East Side, Milwaukee, WI, 53202

Emma was so great with our dog Gus! She was very professional, took the cutest photos and was super prompt with her responses. We will definitely book her again!

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Margaret A.
Sitter Profile Image: Emily V.
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Emily V.
from
$16
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
12 years of experience
Walker's Point, Milwaukee, WI, 53204

Emily was incredibly responsive to messages and was able to come by on short notice to do a meet and greet prior a few scheduled walks we unexpectedly needed later that day. In the pictures, it looked like our dog Ducky had a great time.

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Sabrina C.
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The median cost per walk for dog walking in Hillside is $20

Dog parents share their Rover experiences - Hillside

1 / 1
5.0 out of 5 stars

Yesterday was the first time walking our dog. Jessica communicated when she would arrive, when walking our dog, where they walked and shared photos of our dog taking a walk. I was out of town and felt very confident that Jessica was taking good care of our dog. We will have Jessica take care of Louie, our dog, again.

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Vicki H.
Dog Walking
5.0 out of 5 stars

Travis is so kind and knowledgeable, I felt comfortable with him right away. My dogs were also comfortable with him very quickly and that means a great deal to me. He has been reliable and a great communicator.

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Amy N.
Dog Walking
5.0 out of 5 stars

Madeline did a great job walking my puppy Cody! Excellent communication and she followed all instructions well!

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Jessica W.
Dog Walking
5.0 out of 5 stars

Great with Teddie! He was so tired at the end of his walk, much needed day for me lol 10/10 would book again

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Audree H.
Dog Walking
5.0 out of 5 stars

Maggie is great! She went above and beyond to build trust and comfort with Pippin and she always provides detailed messages on how their visits go.

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Mikala H.
Dog Walking
5.0 out of 5 stars

Alex is an excellent dog walker/caretaker. My dogs love her and she is 100% reliable. She goes out of her way to help her clients. Her communication is excellent and timely. Highly recommend.

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Amy N.
Dog Walking
5.0 out of 5 stars

Autumn was able to help me last min walk my dog and feed him. Very easy to communicate with. Will definitely use her in the future.

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Jeffrey K.
Dog Walking
5.0 out of 5 stars

Katie has been wonderful from the time we booked to walking our boys Pickles and Brownie. Thank you for taking care of them and your great communication.

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Cody Y.
Dog Walking
5.0 out of 5 stars

Rebecca was very good at communicating. Quickly got back to me when I was looking for a person to walk Knox. Very polite and nice.

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Jeffrey K.
Dog Walking
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!

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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!

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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.

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Sabrina C.
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!

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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!

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Elizabeth 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!

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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!

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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.

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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.

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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

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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!

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Noah S.
Dog Walking
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