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: Clairissa H.
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Clairissa H.
from
$22
per walk
5.0 out of 5 stars
• 7 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: Desirae W.
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Desirae W.
from
$25
per walk
5.0 out of 5 stars
• 9 reviews
6 repeat clients
20 years of experience
Edgerton, WI, 53534

About: You know those people that get obnoxiously excited whenever they see a dog out in public? Yup, that's me! I have been a dog lover/owner my whole life. They are my definition of pure joy and bliss. We rescued our pup, Bella, back in April and while she was pretty much perfect from the get-go, we did work with her so she could be the best dog she can be! Now we spend many days of the week traveling to the local dog parks or exploring and finding fun trails or places to go! I am currently working part time, usually the start to my shift is around 5pm if I work that day. I spend my days outside and being as active as I can with my pup and my son! I live in a cozy home where dogs are always welcomed on the furniture, we do crate Bella when we leave the home which is usually never for very long. We have a very large yard although it is not fenced, but I do have multiple cables for some running around time outside when we are not out and about.

Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$26
per walk
4.9 out of 5 stars
• 62 reviews
11 repeat clients
8 years of experience
Janesville, WI, 53546

“Overall a great person. Very easy to work with, easy to reach, fast reaponses, punctual... Took care of our dogs by giving them walks while we were on vacation. The pups loved Allison. Thank you for everything!!”

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Dillon D.
Sitter Profile Image: Dayna V.
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Dayna V.
from
$25
per walk
5.0 out of 5 stars
• 24 reviews
6 repeat clients
25 years of experience
Stoughton, WI, 53589

“Dayna took care of Sammy for two walks this week and she was so sweet to him. She followed the instructions perfectly and even gave him extra love and carrots. You can tell she really cares about the fur babies as we do and we really appreciated her kindness! Thanks so much again!”

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Alixandria C.
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: Somer S.
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Somer S.
from
$12
per walk
5 years of experience
Stoughton, WI, 53589

About: I grew up on a farm, which is pretty much where my animal obsession began! I was surrounded by cows, pigs, horses, chickens, cats, dogs — basically if it had fur, feathers, or hooves, I probably helped take care of it. Growing up around so many different animals taught me a lot about patience, responsibility, and how every animal has their own unique personality. Ever since then, animals have just naturally been a huge part of my life! I’m a full-time nurse with a flexible schedule, since I only work 3–4 days a week. That means I have plenty of time, energy, and attention to dedicate to your furry friends! Whether it’s walks, playtime, cuddles, or just keeping them company, I love making pets feel safe, happy, and cared for while you’re away. I accommodate to every pets needs! I have crates, I do structured playtime and go on long walks to exert energy. I also have a friendly dogs who would love to keep your pet company.

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: Joni V.
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Joni V.
from
$16
per walk
5.0 out of 5 stars
• 5 reviews
45 years of experience
Stoughton, WI, 53589

About: I have pet-sitting experience for all kinds of animals. I've always loved pets and have a house full of chickens, rabbits, cats, a snake, birds, fish and dogs. I am a respectful and accommodating person, happy to give you regular updates, send pictures, and if you would like, collect your mail or water your plants. I am organized and I will ensure your home is the same upon your return. I'll be glad to walk your dog(s) in the morning and/or in the evening. We can gather these finer details of your pets via email. I have experience with all kinds of animals. From raising them to providing proper space for them as well as long term care. Chickens, Great Danes, reptiles, you name it. I've owned many animals all my life and I want to continue to add more experience by sharing my time with other pets. Caring for all kinds of animals brings me incredible joy! Ensuring they have fresh food and water, exercise, stimulation, and love is of the utmost importance. I am flexible and can work with you to suit the needs of your pets. I'm comfortable giving medications too.

Sitter Profile Image: Madigan U.
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Madigan U.
from
$15
per walk
3 years of experience
Fort Atkinson, WI, 53538

About: I have taken care of dogs my whole life from family dogs to neighborhood dogs. From walks to just potty breaks I can provide the best care. I am currently training my own puppy to be the best hunting companion. He has learned to love his kennel and that it is his quiet space. I work part time Monday through Wednesday I am home by 2pm but need time to let my own puppy have some outside time. Thursday and Friday I am home all day other than the occasional appointments. I am able to spend up to two hours with your pet getting the wiggles out or learning some of the basics. Weekends are my family time so I am mostly unavailable other than a random Saturday if my partner ends up working. At my home we are fenced in on 3 sides from neighbors but I have a tie out available. At your home I am comfortable with crates or not and Im willing and able to clean up any mess your furry companion may make. I am comfortable with walking with a harness or not.

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: JESSICA P.
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JESSICA P.
from
$30
per walk
5.0 out of 5 stars
• 17 reviews
4 repeat clients
20 years of experience
McFarland, WI, 53558

“Good with our dogs. On time and helpful to work with.”

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Irene C.
Sitter Profile Image: Kendra B.
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Kendra B.
from
$15
per walk
30 years of experience
Madison, WI, 53716

About: I grew up with dogs, cats, and horses, and have experience in oral med administration with both cats and dogs. I have a soft spot for the big dogs (they're lap-sized if you commit!) and am currently training for a half marathon, so getting good long walks or jogs in will be built into my day! I work remotely, so keeping your pretty company through the day is no problem! I start my mornings early work a run or walk so your dog will definitely get his steps in. As I'm in your home, your instructions are paramount. You know your pet better than anyone, and I am happy to keep their normal routines in place. I like getting to know each animal and their unique personality, and while I *love* giving snuggles and pets, I understand some pets prefer their space.

Sitter Profile Image: Christine D.
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Christine D.
from
$15
per walk
4.8 out of 5 stars
• 22 reviews
7 repeat clients
10 years of experience
Cottage grove, WI, 53527

About: I always had a dog. The house isn’t a home if you don’t have a dog. Family brings there dog over. Every one gets along I’m working part time . Will have time to play and walk your dog. I care for dogs. I have a dog name Louie. We’re always outside I have a big fenced in yard . I have a dog so my house is dog proof. I have a one story house on a quiet street.

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: Cara H.
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Cara H.
from
$15
per walk
5.0 out of 5 stars
• 2 reviews
2 repeat clients
1 year of experience
Jefferson, WI, 53549

About: I have a rescue dog so I have a lot of patients! I’ve always loved animals and I’m working towards volunteering for a foster company! I am working part time so I have a lot of time on my hands to help take care of others pets! I will be able to spend a lot of quality time with your pup! I have a crate if needed for your dog. I do have a fenced in backyard that has multiple toys for dogs. If I come to your house I will follow any rule you have for animals and people in your home.

Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 51 reviews
20 repeat clients
30 years of experience
Brentwood Village, Madison, WI, 53704

“Elizabeth was great with our dog Cash giving us updates with pictures and giving him nice long walks. Will definitely be using her again and highly recommend her.”

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Amy L.
Sitter Profile Image: Erin V.
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Erin V.
from
$20
per walk
5.0 out of 5 stars
• 6 reviews
1 repeat client
10 years of experience
Marshall, WI, 53559

“Did a fine job filling in for my usual walker. Thank you!”

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David L.
Sitter Profile Image: Erika M.
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Erika M.
from
$30
per walk
5.0 out of 5 stars
• 5 reviews
5 years of experience
Fort Atkinson, WI, 53538

About: Caring for others (especially animals) is truly my passion! I was a nanny for over 5 years which opened me up to pet care as well. Since most families I worked for had pets, I took on the responsibility of caring for them as well as their children. Hi there! Just a little bit about me! Caring for others (especially animals) is genuinely my passion! I was a nanny for over four years which opened me up to pet care as well. Since most families I worked for had pets, I took on the responsibility of caring for them as well as their children. I do not work outside of the home which means I can dedicate all of my time to your pet! I usually take one booking at a time, so if your pet doesn’t get along with other pets that’s no problem.

Sitter Profile Image: Carolina H.
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Carolina H.
from
$20
per walk
3 years of experience
Janesville, WI, 53545

About: I have experience caring for a variety of pets with different needs and routines. I have taken care of a 1-year-old cat along with 3 other adult cats, including a cat who required at least 30 minutes of playtime and interaction every day. I have also cared for a large dog who ate home-cooked soup mixed with his food at specific feeding times, as well as a husky who stayed in an air-conditioned dog house unit and required daily vitamins and attentive care. I am good at following direction for the desired care you and your pet need. I work remotely and any activities I plan I would plan around a schedule if at all with the pet in mind. I will plan in advance for the openings I have in my schedule to permit me to be with the pet. I typically stay in the pets home to create a less stressful environment for the pet and go about its daily routine as instructed by the pet owner. I will stay as long as required by the pet owner or stay in a guest bedroom all day depending on what makes the pet owner most comfortable with.

Sitter Profile Image: Hailey R.
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Hailey R.
from
$15
per walk
5.0 out of 5 stars
• 4 reviews
2 repeat clients
9 years of experience
Sun Prairie, WI, 53590

About: What sets me apart is my dependable, loving care. I treat every dog like family, giving patient attention, walks, playtime, cuddles, and plenty of love. I work mornings in retail. Then have college classes in the mornings and later in the afternoon into the evening. Some days I am done with classes early. I have more flexibility on the weekends. I adapt to each pets needs. I grew up with cats and dogs, and provide walks, cuddles, space if needed, plus updates, photos, and lots of love, care, and attention.

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

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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 September 2026, there are 1,637 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 services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Hillside.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s 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 Rover Guarantee , 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 Rover's Trust & Safety page .

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

  • 91% of walkers can help with special care needs
  • 96% 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 short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

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

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