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: Clairissa H.
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Clairissa H.
from
$22
per walk
5.0 out of 5 stars
• 8 reviews
1 repeat client
5 years of experience
Cambridge, WI, 53523

“Clarissa was so great with my puppy! She was responsive, responsible and resourceful about keeping him entertained when I had to be gone for four days. I recommend her highly!”

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Virginia B.
Sitter Profile Image: Julia S.
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Julia S.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
7 years of experience
Stoughton, WI, 53589

About: My first job was as a kennel attendant at a local vet clinic where I learned a lot about animal care. I have also worked at a boarding facility. Since working there, I have started my own pet sitting service called “Bodens Buddies”. I started this service for a number of reasons; one, to give my dog Boden unique social opportunities, and two, because I believe pets thrive in a home setting even if it’s not their home. I am currently working part time as I continue my college studies, so I have plenty of time to commit to your pet(s)! My schedule is flexible! I have a fenced in yard and a friendly dog of my own. I also have two cats who can be spaced in another area if needed.

Sitter Profile Image: Trinity G.
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Trinity G.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
• 19 reviews
5 repeat clients
12 years of experience
Stoughton, WI, 53589

“Trinity has been wonderful with our kitty boy! She has consistently been walking him twice a week and she responds very quickly! Our pets love her!”

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Gillian H.
Sitter Profile Image: Sheena V.
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Sheena V.
from
$20
per walk
18 years of experience
Stoughton, WI, 53589

About: I’ve always enjoyed being around animals and caring for them. I have experience with dogs and cats, including feeding, walking, cleaning up after them, and spending time playing and keeping them comfortable. I pay close attention to each pet’s personality and needs, whether they’re energetic or more shy and relaxed. My goal is to make sure every pet feels safe, cared for, and loved while their owner is away. I’m reliable, patient, and treat every pet like family. Pet care fits naturally into my daily life. I currently have a flexible schedule, which allows me to be available throughout the week for walks, drop-ins, or extended care. With my background as a former dog groomer and long-term experience in the pet industry, I’m very comfortable caring for animals and enjoy making them feel safe, calm, and cared for. I care for pets by following their normal routine closely, including feeding, walking, playtime, and any medications. I prioritize safety, cleanliness, and comfort, and I’m experienced in handling different temperaments from my time working in boarding facilities and pet care. My goal is to make pets feel safe and cared for as if they were my own.

Sitter Profile Image: Madi D.
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Madi D.
from
$35
per walk
5.0 out of 5 stars
• 8 reviews
4 repeat clients
10 years of experience
Cottage Grove, WI, 53527

About: I have taken care of pets my whole life. My Dad went to school to be a Veterinarian, so we have always been around different animals. I have two cats at home, and recently just lost my beloved dog, Lexi! I currently work as a flight instructor so my schedule is very flexible! I typically start later in the day or early in the morning. Plenty of time to help out!! I can walk, feed, clean-up after any pets. I have no preference, little, big, cats and dogs. I am able to understand pets all have very special needs and want to fulfill those.

Sitter Profile Image: Evan T.
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Evan T.
from
$15
per walk
11 years of experience
Fort Atkinson, WI, 53538

About: I started taking care of animals, both cats and dogs, 11 years ago! I've provided animal care services for family members, friends, and for other families through referrals! It's extremely enjoyable to me when I get the privilege to take care of a new animal.! I never want a owner to worry their animal might be too much for me as I've dealt with a variety of dogs and cats in both size and temperament- I can handle practically anything! A majority of my animal care (if not all) has involved me staying the night for a week or two with the animal/s. I love to spend a lot of time and be active with the animals! Whatever was needed and instructed in care maintenance for a clients animal- I've happily handled with ease! As of right now I'm doing freelance work, so my availability is pretty open! If you select me for a specific pet care need, we can discuss it together and come up with a plan that best fits your needs! I care for my pets as if they were my own and through the clients instructions on how to care for their animal! Whatever the client is asking of me and for their animal needs, I will happily fulfill with ease and make sure their pet is taken care of!

Sitter Profile Image: Hailey M.
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Hailey M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 47 reviews
11 repeat clients
10 years of experience
Madison, WI, 53704

“Hailey is so great to work with and I’d hire her again anytime! She is extremely responsive and always gives great pupdates. Plus our pups seem to love her!”

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Claire H.
Sitter Profile Image: Lynne O.
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Lynne O.
from
$25
per walk
5.0 out of 5 stars
• 12 reviews
1 repeat client
30 years of experience
Fitchburg, WI, 53711

“She was the perfect person to walk my doggie.”

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Zorba P.
Sitter Profile Image: Emilee K.
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Emilee K.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
11 years of experience
DeForest, WI, 53532

About: I am an aspiring vet student who has 10 plus years of experience with cats and dogs both owning and sitting for. I have medical knowledge that other sitters may not have as I work at an ER for pets as a nurse! I am extremely flexible with my time and availability and will ensure that your pet gets the well-deserved love and care they need! As a bonus, I can offer nail trims, sanitary shaves, and ear cleanings during their stay if requested! I'm currently working part time night-shift, so I will have plenty of time to play with your pets! I make my own schedule during the day, so I can easily work around your pet's needs. I have a dog and cat myself at my apartment that are well socialized to be around other dogs. I can accommodate up to two dogs in my apartment if needed and can also go to your home if preferred. For cats, I find it best to go to them. I do not have a yard, but my apartment complex is pet friendly with a play area and lots of walking trails nearby.

Sitter Profile Image: Alexandra H.
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Alexandra H.
from
$20
per walk
5.0 out of 5 stars
• 10 reviews
1 repeat client
5 years of experience
Madison, WI, 53704

About: Hi everyone! My name is Alexandra but I tend to go by Lexy. I have had dogs and cats and so many other animals in my household since before I was even born. My mom grew up on a big farm so she was used to being around animals. She wanted to make sure she had the same experience for my brother and I. I have been a part time dog sitter through word of mouth mainly. I just recently graduated from college with my bachelors in Public Health and am looking for a fun filler throughout my summer while I plan next steps. Animals (especially dogs) are my safe space. So please, entrust in me with your fury friend and I promise you will not regret it! I am currently only working part-time on weekends. So schedule is extremely open and extremely flexible. I am also available to do over nights as I have someone at my house who can watch my animals! I will not be offering any services at my own home as I have a pretty full house of animals. To sustain their comfort I want to keep this separate. At my house I have a fenced in yard but a large yard outside that fence the dogs are able to roam. They have an electric fence so they know how far they are supposed to go.

Sitter Profile Image: Dawnlea W.
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Dawnlea W.
from
$15
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Janesville, WI, 53546

About: I’ve grown up with pets my entire life, cats and dogs. I have experience with all age ranges of pets. I enjoy taking care of mine and my family members pets! I often watch my parents 2 year old energetic boxer mix, as well as 3 cats, one who has heart failure. I also love spending time with my sisters 5 year old mini doxie. I’m comfortable cleaning up messes, cleaning litter boxes and providing basic medical needs. I look forward to meeting the furry important members of your family and providing the best care I can! I have an open availability for Monday-Friday from 6am-3pm. I’m available for longer walks if needed or short in and out trips. I take my parents dog Willie on walks around local parks, he’s a very energetic dog and likes to pull. So I take it one step at a time with him and give him ample time to soak in all the enrichment of the environment around us.

Sitter Profile Image: Allison C.
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Allison C.
from
$20
per walk
5.0 out of 5 stars
• 3 reviews
20 years of experience
Fitchburg, WI, 53711

About: I love any and all animals. I have consistently been around animals since the day I was born. I have grown up with dogs and have 20+ years of experience caring and being responsible for them. I now have my own dog, a four year old corgi named Millie. I recently switched to a remote position, so I am available to care for your pet at home any day of the week with any kind of schedule. When I am not at work, I am home enjoying the day with my dog, Millie. Depending on the animal, Millie likes to play or will give them the space that they need. We go on lots of walks, play fetch, and work on puppy puzzles. I have a dog run in my building in case the weather doesn’t allow a long, outdoor potty break. There is a park that I frequently visit with my dog a couple of blocks away. Because I am a nurse, I can care for any of your pets medical needs and I will always keep an eye on them to make sure they are safe.

Sitter Profile Image: Taylor K.
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Taylor K.
from
$27
per walk
5.0 out of 5 stars
• 2 reviews
10 years of experience
Regent, Madison, WI, 53726

About: I’ve been taking care of dogs for 10+ years, and have two of my very own! I am extremely passionate about my love for dogs, and would love to be able to meet more and help you out! I currently work from home doing social media and marketing, so my schedule can be pretty flexible. Once June starts, my Tuesday and Thursday nights are full from about 3-8 but can always let your dog out before and/or after! Once end of August hits I head back to school in Madison, WI! I care for pets very deeply. I believe that all pets deserve the best life they can possibly live. My two dogs are taken on at least 1-2 walks a day, while getting play time in our back yard. Exercise is extremely important to dogs, as well as chill time:)

Sitter Profile Image: Kirstin B.
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Kirstin B.
from
$35
per walk
5.0 out of 5 stars
• 8 reviews
1 repeat client
20 years of experience
Hartland, WI, 53029

“Kirstin is very committed to caring for her dog friends. Great communication and follow through!”

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Sarah F.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$20
per walk
5.0 out of 5 stars
• 13 reviews
1 repeat client
16 years of experience
Alverno, Milwaukee, WI, 53220

About: My unconditional love for all animals. Every cat or dog that I meet I treat and cherish as if they were my own fur baby. I do work a full time job, 8-4 Mon-Fri. However, I am looking to use some of my free time taking care of your fur baby! I do my best to maintain whatever routine you have with your fur baby. I am willing to go the extra mile to make your pup feel safe and comfortable while you are away.

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

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  • 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.

How to book dog walking

  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

FAQs for Dog Walking - Hillside

Frequently asked questions about Rover

As of October 2026, there are 1,610 sitters on Rover offering Dog Walking across Hillside. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Hillside. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include , the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Hillside after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the walk begins.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the , which provides up to 25,000 in eligible veterinary care reimbursement.

Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to 25,000 in eligible veterinary care. For more details, visit .

Yes, you can find walkers who have experience with handling special pet needs in Hillside. On Rover:

  • 88% of walkers can help with special care needs
  • 92% can help with giving oral medications or injections
  • 97% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first .

walkers on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.

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