Dog Walking in Hillside, Milwaukee, WI

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

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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.

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Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Jessica Z.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
188 reviews
54 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: Elise D.
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Elise D.
from
$14
per walk
1 repeat client
25 years of experience
Riverwest, Milwaukee, WI, 53212

On time and reliable!

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cameron l.
Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
134 reviews
47 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: Meghan E.
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Meghan E.
from
$20
per walk
5.0 out of 5 stars
20 reviews
2 repeat clients
8 years of experience
Avenues West, Milwaukee, WI, 53233

About: Graduate student. Very organized and an absolute animal lover! Feel free to reach out for any pet needs! Love your dog like I love my own I currently work part time and go to school so I have time to actively walk a dog and give it my full attention. I am usually free all day on weekends and mornings on weekdays I will create a safe space for your dog to play and pay full attention to your animal. Any necessary information given to my by the owner I will make sure to pay extra attention to jt

Sitter Profile Image: Christopher R.
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Christopher R.
from
$15
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Kilbourn Town, Milwaukee, WI, 53203

About: Hello! I am located in downtown Milwaukee and I work fully remote so I am able to stay for overnights/long weekends if needed! My remote work schedule allows me to work a very flexible schedule around the needs of your pets! I have grown up with various pets, both dogs and cats at the same time and individually. I currently live with 2 cats, and I regularly care for friends and coworkers dogs. I am fairly active and regularly work out; taking dogs on walks or runs will be no issue for me. I currently work fully remote, I am able to regularly stop off around lunch hour for any dog care needs. I am able to spent the entire day and night with any pets you have if you provide me 1 day notice to set up my workstation at your home and you have high speed internet. Due to the fact that I live in an apartment that does not allow dogs, unfortunately I will not be able to care for pets in my home. I am only open to care for your pets in your home at this time.

Sitter Profile Image: Lauren S.
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Lauren S.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
10 reviews
6 repeat clients
10 years of experience
Milwaukee, WI, 53203

First time using rover and this was a great beginning! Violet seemed happy and got her exercise in. Will be using Lauren again!

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Sarah H.
Sitter Profile Image: Ashley M.
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Ashley M.
from
$20
per walk
5.0 out of 5 stars
46 reviews
31 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

Thanks to Ashley for being available and flexible when we needed a last minute dog walking!

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Abby
Sitter Profile Image: Jamie S.
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Jamie S.
from
$14
per walk
5.0 out of 5 stars
26 reviews
11 repeat clients
17 years of experience
Avenues West, Milwaukee, WI, 53233

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

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Gabriel S.
Sitter Profile Image: Benjamin S.
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Benjamin S.
from
$15
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Lower East Side, Milwaukee, WI, 53202

About: I am a dog lover, have taken care of my own dogs and my parents for years. I love taking them for walks or especially to the park or beach to play fetch! I am a law student so my schedule is set but should be able to help regularly with any pet. Happy to accommodate most requests if they are within reason. Regular potty and walk breaks as needed and will provide food and water according to instructions given. No other pets in my home so it will be a very relaxed environment.

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

First time using Rover! Excellent experience. Travis was awesome. Prior to her first walk with him, he came over for a meet and greet which was very helpful. Right away, Whinnie could tell he was a dog lover. He also was very responsive to all of my questions I had in person and via the app. We will definitely use him again! It is such a good feeling to know our pup is being taken care of.

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Molly S.
Sitter Profile Image: Aubrey A.
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Aubrey A.
from
$20
per walk
5.0 out of 5 stars
61 reviews
16 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!

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Blake H.
Sitter Profile Image: Mikalanne T.
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Mikalanne T.
from
$18
per walk
5.0 out of 5 stars
43 reviews
13 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!

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Irene S.
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: 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

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!

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Sarah H.
Sitter Profile Image: Samuel G.
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Samuel G.
from
$16
per walk
10 years of experience
Lower East Side, Milwaukee, WI, 53202

About: Although I currently have two cats, I grew up with dogs and would love to take yours on a walk. I’m well versed with treat administration, petting, throwing balls, and playing tug of war. I pet sit for two of my friends’ dogs when they are out of town here in Milwaukee. I am a 4th year medical student so my schedule is flexible sometimes. I am basically free for the next two weeks every week day. After that my schedule will vary a bit. My kitties are indoor only and we play a lot with toys, laser pointers, and such. They are quite the little snugglers and love attention

Sitter Profile Image: Haley P.
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Haley P.
from
$18
per walk
7 years of experience
Brewer's Hill, Milwaukee, WI, 53212

About: I’ve taken care of cats and dogs for several years now. Friends and family will reach out to me to walk, feed, and play with their pets as well as tend to the poopy part of pet parenting. I work from home, so I have the flexibility to check in on your pets any time of day. I also have a car and like downtown, so I have access to the Milwaukee suburbs. Because I have a reliable car, I can easily drive to your home to tend to your pets. I will follow your instructions on how best to care for your pets while going above and beyond by simply just staying with your pet so they receive socialization.

Sitter Profile Image: Quinesha F.
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Quinesha F.
from
$16
per walk
5.0 out of 5 stars
31 reviews
4 repeat clients
20 years of experience
Riverwest, Milwaukee, WI, 53212

About: welcome! 🔔 please confirm you have read my profile entirely when sending your booking request 🔔 Dogs have been apart of my life for over 25 years. I learned body language, how to care for them, and how to be patient and communicate with them from my amazing Grandfather. They truly bring me joy! I treat each pup as if they’re my own during our time together. 🐾 I will do everything I can to accommodate your pup’s needs & your desires. Whether it’s walks vs runs in the yard, administering medication, or preparing food, if I’m able to do it consider it done! As a pet parent, I know how stressful it can be to find reliable care. With that in mind, I strive to provide the BEST care for your dog the first time in order to lighten your load; giving you the peace of mind knowing your fur baby is in excellent hands. 🐶 I no longer work remotely, so I’m not available for drop ins, walks, or daycare M - Th prior to 5PM. I am willing to board throughout the week, but please note your pup will be home alone for about 11 hours. Fri-Sun, I am available all hours. 🚨 MEET & GREETS ARE MANDATORY FOR ALL SERVICES 🚨 Daycare & Boarding: - Please be mindful that I do have a dog of my own. If you know your dog does not do well with other dogs, please do not request a boarding or daycare. I am open to doing daycare in your home for the pups that prefer to be alone. request house sitting & I will adjust the rate! - my home is best suited for the chill guys and gals. lots of soothing music, lounging, & cuddles 💓. Honey Bun is very reserved inside & gets stressed around high energy dogs. To keep all involved happy & safe, please do not book daycare or boarding if your dog is an energizer bunny. I will be glad to drop in, walk, or do daycare in your home though! 😃 - I have a secured, fenced in yard. I am not willing to take any dog to the dog park. Both the front and back doors have additional doors down the stairs, so the chance of an escape is very close to zero! - I crate all dogs when I’m leaving the home, including Honey B even though she typically is not crated. in special situations, I’m okay leaving your dog to roam a designated area, but that is rare and will be discussed prior to the booking. - I do not have any guests while your dog is in my care. Drop Ins/Walks/House Sitting: - I ask that no other humans are in your home when I come over for drop ins, walks, or housesitting unless previously discussed. - Please book a drop in if care outside of walking is needed. - Please assure all animals that need care are listed individually on your profile. I love surprises, but not when it comes to this! - When coming into your home, I will always leave it just as I found it. I will only enter authorized areas as necessary to care for your pet(s). Please assure that all supplies are provided. 🐾 - We will discuss specific schedules for each housit. Some people prefer longer day time care with no overnight, or moderate daytime care + nights. We will workout the perfect schedule for you, your pup, and me 😊. I am NOT available for constant care (24 hours) as I will need to check in with my own dog & maintain my personal life with errands + self care.

Sitter Profile Image: Valerie S.
Verified Enhanced Background Check
Valerie S.
Star Sitter
from
$23
per walk
5.0 out of 5 stars
62 reviews
16 repeat clients
11 years of experience
Milwaukee, WI, 53202

Marvin is a Parsons Russel terrier mix. He's usually cautious of strangers and will bark and bark. Valene quickly gained his trust. By the third walk, he was bolting out the door with her. Valene was always on time and reported on his "activities" when they returned. I can highly recommend Valene.

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William B.
Sitter Profile Image: Kayla A.
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Kayla A.
from
$25
per walk
5.0 out of 5 stars
70 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 ;)

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Chalani E.
Sitter Profile Image: Benjamin R.
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Benjamin R.
from
$20
per walk
5.0 out of 5 stars
1 review
4 repeat clients
2 years of experience
Milwaukee, WI, 53202

About: Experienced in long term pet care, taking care of dogs for extended time periods when owners are on vacation and everyday experience taking care of pets while families are working, including drop ins and dog walks I work remotely and have a lot of free time open during the day for drop ins and dog walks. I’m available in the mornings, afternoons, and nights! Will respect any rules of the house and am very open to watch / play with the dogs in any way they’re comfortable with and used to

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Hillside dog parents share their Rover experiences

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5.0 out of 5 stars

Dogs enjoyed their walk and got the chance to poop and pee lots! Also impressed she handled both of my larger dogs with such ease, will absolutely be booking with her for any future walks !

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Izzy D.
Dog Walking
5.0 out of 5 stars

Sydney has been great! She’s amazing with my dog, communicative, and flexible. I would definitely book her again!

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Bethany D.
Dog Walking
5.0 out of 5 stars

Elise did a fantastic job taking care of Luci this week! Reliable, punctual, and a great communicator.

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Katie H.
Dog Walking
5.0 out of 5 stars

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.
Dog Walking
5.0 out of 5 stars

I really appreciated Elizabeth's willingness to do a meet and greet before the first walk. She was super patient and understanding with my anxious pup. Would recommend!

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Melissa D.
Dog Walking
5.0 out of 5 stars

Carrianne is professional and very responsive! My dog absolutely loved her. Could not recommend more!

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Emily K.
Dog Walking
5.0 out of 5 stars

Hannah is very personable. She is easy to communicate and work with and very obviously loves critters. I am so grateful for her entertaining my ranbunctious dog while I am at work.

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Silas S.
Dog Walking
5.0 out of 5 stars

Selena is so amazing! She is super reliable and takes such good care of my puppy. She treats him like her own and he loves her so much. She always send me pictures while they’re out walking and I love to get updates like that. It brings me a lot of peace of mind to know he’s in such good hands when he’s with her.

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Amy N.
Dog Walking
5.0 out of 5 stars

We just moved to the area and were nervous to get someone new to take care of Zuko but everything went so well and we appreciate the communication, meet and greet, and the overall care! 😊😊

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jordan r.
Dog Walking
5.0 out of 5 stars

Nikki was a life saver for my anxious Pomeranian! The owner of the ARBNB complained my dog barked when we left( I did not know my dog barked or that the owner lived on premises). I had Nikki another time we visited for Wi State Fair last year and I had peace of mind. She is the best pet sitter you could ever have! She sends pictures too!

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Holly B.
Dog Walking
5.0 out of 5 stars

Catherine was great! I booked her for a last minute 30-min walk. She arrived on time and provided detail updates and photos of her time with Penny.

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Shelby I.
Dog Walking
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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.