Dog Walking Hillside

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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: Max M.
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Max M.
from
$15
per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
14 years of experience
Murray Hill, Milwaukee, WI, 53211

Max was AMAZING with my dog Blue. He was reliable & very trustworthy. He took my dog on a nice long walk and even played ball with him until he was tuckered out. Such peace of mind while I had long days at work. We will definitely be reaching out again for longer work days. Thank you, max!

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Julia F.
Sitter Profile Image: Alexandra I.
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Alexandra I.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
27 reviews
5 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: Jackie C.
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Jackie C.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
150 reviews
56 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: Rebecca M.
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Rebecca M.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

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.
Sitter Profile Image: Jessica B.
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Jessica B.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
19 reviews
12 repeat clients
17 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!

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Chadwick and Mayara M.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
214 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: Jessica K.
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Jessica K.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
44 reviews
12 repeat clients
15 years of experience
Northpoint, Milwaukee, WI, 53211

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.
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: 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: Jodi C.
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Jodi C.
from
$20
per walk
5.0 out of 5 stars
36 reviews
11 repeat clients
40 years of experience
Harambee, Milwaukee, WI, 53212

Thank you so much!! Helped me out on short notice!! :)

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Mariah S.
Sitter Profile Image: Madeline R.
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Madeline R.
from
$15
per walk
5.0 out of 5 stars
6 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: Melissa A.
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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

If you’re looking for a dog walker I highly recommend Melissa. She was prompt, professional, and took excellent care of my small dog. She asked relevant questions about my dog before leaving for the walk, and afterwards gave me a thorough update of the walk. I feel comfortable with her in charge of my beloved sweet furry friend!!

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Julie B.
Sitter Profile Image: Riley L.
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Riley L.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
8 reviews
3 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 :)

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Emily D.
Sitter Profile Image: Natalie K.
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Natalie K.
from
$16
per walk
1 repeat client
13 years of experience
Milwaukee, WI, 53202

About: I have been around dogs my whole life and have had lots of experience with walking dogs of all shapes and sizes! I enjoy going for walks with dogs. I’m a high school teacher on my summer break, so I am available almost everyday at all times of day, especially mornings and mid afternoon around 3 or 4pm I love to take dogs on walks in different areas! For example, I love to walk the bike path, neighborhoods, the beach, parks, etc! Any environment works.

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: Ixzel R.
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Ixzel R.
from
$14
per walk
5.0 out of 5 stars
2 reviews
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: Mikalanne T.
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Mikalanne T.
from
$19
per walk
5.0 out of 5 stars
56 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: Karina J.
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Karina J.
from
$10
per walk
6 years of experience
Kilbourn Town, Milwaukee, WI, 53205

About: My name is Karina and I've owned and cared for cats my entire life. While I've always wanted to add a dog into my family, my father is allergic. However, I never resist mingling with dogs whenever I can! I'm very experienced with caring for cats, including feeding, cleaning the litter box, etc. I am so open to home visits to check in on dogs as well as walk them. Outside of animals, I'm a pharmacist! Additionally, I love to travel, go to new restaurants, and cozy up with a good book. Feel free to contact me with any questions you may have! I do work full time (~ 11 hour shifts) so an animal who would need 24/7 care may not be the most ideal for my schedule, however I do have consecutive days off pretty frequently. I will listen to you and your wants/needs and how you care for your animals. I know some owners love to keep their dogs in the crate when they're away, and I would do the same.

Sitter Profile Image: Jake R.
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Jake R.
from
$20
per walk
5.0 out of 5 stars
14 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: Alexandria C.
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Alexandria C.
from
$20
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
15 years of experience
Yankee Hill, Milwaukee, WI, 53202

Alexandria has been amazing with our puppy! She’s very reliable and understanding of our puppy’s quirks! Can’t recommend enough 🙂

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Bronwyn & Sean D.
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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

Alex is completely reliable and cares about the dogs in her care. She goes above and beyond for her clients and is always friendly and easy to work with. You won’t find a better person to help with your pets.

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Amy N.
Dog Walking
5.0 out of 5 stars

I’ve booked Max a few times to walk my sweet dog blue while I have long days at work. He is SO happy to see him each time. Brings me such peace of mind knowing my boy blue is taken care of, loved and gets to go potty and throw ball while I’m working long days. We will continue to choose Max anytime I need mid day support. Bonus pictures of blue throughout his walk are so sweet. Thank you, max!!! 🫶🏼

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Julia F.
Dog Walking
5.0 out of 5 stars

Lea is awesome. She is very responsive and takes great care of our puppy. He loves her! Would recommend!

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Tori M.
Dog Walking
5.0 out of 5 stars

Miriah was great. We weren’t home and Miriah texted me when she arrived, during the walk, info about feeding Louie, etc. I felt very confident that our dog was well taken care of.

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Vicki H.
Dog Walking
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

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

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
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