Dog Walking Hillside

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

End
Search

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.

1 / 1
Sitter Profile Image: Jackie C.
Verified Enhanced Background Check
Jackie C.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
153 reviews
57 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

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.
Sitter Profile Image: Rebecca M.
Verified Enhanced Background Check
Rebecca M.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
12 reviews
5 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.

Profile image
Jeffrey K.
Sitter Profile Image: Madeline R.
Verified Enhanced Background Check
Madeline R.
from
$15
per walk
5.0 out of 5 stars
10 reviews
2 repeat clients
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!

Profile image
Jessica W.
Sitter Profile Image: Sophia B.
Verified Enhanced Background Check
Sophia B.
from
$15
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
4 years of experience
Kilbourn Town, Milwaukee, WI, 53203

Absolutely wonderful. Highly recommend

Profile image
Ravi J.
Sitter Profile Image: Jessica B.
Verified Enhanced Background Check
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!

Profile image
Chadwick and Mayara M.
Sitter Profile Image: Jodi C.
Verified Enhanced Background Check
Jodi C.
from
$20
per walk
5.0 out of 5 stars
37 reviews
13 repeat clients
40 years of experience
Harambee, Milwaukee, WI, 53212

Jodi is so great! She is very flexible with my last minute booking and has been great with our dog! She presents with great communication as well! Would recommend!

Profile image
Kinga P.
Sitter Profile Image: Jasmine R.
Verified Enhanced Background Check
Jasmine R.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
83 reviews
8 repeat clients
5 years of experience
Murray Hill, Milwaukee, WI, 53211

About: I have experience working with a wide range of different breed and sizes of dogs. I worked at a doggie daycare and it was an absolute joy. I have taken care of dogs since I was young. Been surrounded by pets my whole life! From dogs, cats, snakes, fish, hamsters, rabbits ect. People trusted me from a young age with their pets because they naturally floated towards me. From small dogs to big ones. I have taken care of family dogs and friends of family pets. I always volunteered to do anything that involved animals. Not only do I currently handle dogs as my job but I also do baths! I took care of horses and other farm animals down in SC when I would visit family. My family are know to have ranches so animals have been a keen part of my life I'm taking a break from my part-time at a doggy daycare so I got plenty of hours for you dogs needs! I'm available all week for majority of day. I'm able to follow regular routines if informed by my clients in order to minimize confusion and be more comforting for the pets. When it comes to my client's medications for their dogs, I am punctual with how it's administered to their dog. If given permission, I'd bring treats and have them do fun little tricks to build trust between the pets so I'm not just a stranger

Sitter Profile Image: Jessica K.
Verified Enhanced Background Check
Jessica K.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
47 reviews
14 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: Cathy L.
Verified Enhanced Background Check
Cathy L.
from
$25
per walk
5.0 out of 5 stars
76 reviews
24 repeat clients
20 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Cathy made sure to play with Pepper when she didn't want to walk at night! So helpful

Profile image
Rebecca R.
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Jessica Z.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
218 reviews
64 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! ☺️

Profile image
Markie J.
Sitter Profile Image: Maggie S.
Verified Enhanced Background Check
Maggie S.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
20 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.

Profile image
Jasmine S.
Sitter Profile Image: Alexandra I.
Verified Enhanced Background Check
Alexandra I.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
31 reviews
6 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.

Profile image
Amy N.
Sitter Profile Image: Chelsea R.
Verified Background Check
Chelsea R.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
72 reviews
31 repeat clients
20 years of experience
Harbor View, Milwaukee, WI, 53204

Chelsea did an amazing job walking my pup Leo. She was so responsive and sent updates which always makes me feel at ease. My pup is a nervous Nellie around other dogs and she did a wonderful job managing his behavior. Couldn’t recommend enough!!

Profile image
Nicole P.
Sitter Profile Image: Ixzel R.
Verified Enhanced Background Check
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: 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: Riley L.
Verified Enhanced Background Check
Riley L.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
8 reviews
5 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: Shannon G.
Verified Enhanced Background Check
Shannon G.
from
$20
per walk
5.0 out of 5 stars
1 review
20 years of experience
Kilbourn Town, Milwaukee, WI, 53202

About: Hello! My name is Shannon and I’m available for dog walking, dog sitting and house sitting in the Yankee Hill neighborhood. I work during the day, but my schedule is flexible. I’m a 39 year-old female new to the neighborhood. Please feel free to connect with me through Rover! I'm self-employed and am flexible to dogsit or dogwalk on a daily basis. I'm located in Elm Grove and can make myself available as needed. Thank you! Shannon I occasionally dogsit, dogwalk and sometimes catsit for friends, family and clients. I'm located in Elm Grove and can make myself available as you need. Thank you! Shannon

Sitter Profile Image: Mikalanne T.
Verified Enhanced Background Check
Mikalanne T.
from
$19
per walk
5.0 out of 5 stars
57 reviews
20 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: Romeo V.
Verified Enhanced Background Check
Romeo V.
from
$20
per walk
2 years of experience
Kilbourn Town, Milwaukee, WI, 53205

About: I own two cats of my own with my partner, so I’m very experienced in caring for cats. Additionally, growing up I have cared for dogs of all sizes. Right now, my schedule is very open as I work on developing my own company. This leaves lots of time for quick check-ins with your pets and extended overnight stays. I am very clean in my own home, and I will ensure that I am the same in yours. I will always clean up after myself and after your pets (which goes without mentioning)

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.
1 / 1
View more

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

Dana has been fantastic to work with and has taken great care of my dog, Vincent! She is thorough, attentive to details, and always sends reliable updates during/after her visits. She is also very responsive and flexible whenever last-minute schedule changes come up, which I really appreciate. Vincent and I would highly recommend Dana to anyone in the Milwaukee and Third Ward area looking for a reliable, trustworthy person to care for their pet!

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

Maggie is awesome! Grizzly is a very nervous pup and Maggie was extremely patient, understanding, and kind to him. I highly recommend Maggie to anyone!!

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

Jessica did a great job. Louie (the dog) loves her and was happy and content when we got home. Pictures and walk report Jessica sent to us was very helpful. Takes the worry out of being away. Definitely hope to use her again.

Profile image
Mark W.
Dog Walking
5.0 out of 5 stars

Jacob is the best I will ALWAYS reach out to him first. He went the extra mile and my babies loved him! He took great cate of them.❤️

Profile image
Cathy K.
Dog Walking
5.0 out of 5 stars

Emily came through for me last minute to walk my two dogs this week! She was responsive and provided nice updates. Would highly recommend her. Thank you Emily!

Profile image
Savannah T.
Dog Walking
5.0 out of 5 stars

Jodi is so great! She is very flexible with my last minute booking and has been great with our dog! She presents with great communication as well! Would recommend!

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

Emma was great with our dogs! She gave them the care they needed and lots of extra love, too. She sent updates and photos and was very reliable. We would highly recommend her for pet care.

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

Miriah agreeing to walk Louie was very helpful to my husband and me. She’s very reliable. Second time Miriah walked Louie and plan on having her walk Lou again in the future.

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

I needed a walker yesterday because I couldn’t be physically away from my home, so I was there when Andrew arrived. He texted when he was on his way, arrived promptly, and spent a couple of extra minutes greeting Rosie, on her level, letting her check him out and get comfortable with him - I was pleased. When they were out walking, a friend happened to see them and called me to tell me that she was impressed with how patient and gentle he was with her. He obviously made a positive impression on Rosie because she was very excited when he returned in the afternoon for her 2nd walk. I will definitely use Andrew for my future needs.

Profile image
Susan A F.
Dog Walking
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.

Profile image
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!!! 🫶🏼

Profile image
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!

Profile image
Tori M.
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.

Profile image
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!

Profile image
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

Profile image
Audree 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.

Profile image
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.

Profile image
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.

Profile image
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!

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
1 / 1
Find pet care near you

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local walkers who will treat your dogs like family

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for dog walking - Hillside

Select a filter and find qualifying sitters offering dog walking.

Sitters in Hillside average 3
repeat dog walking clients

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge