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: Clairissa H.
Verified Enhanced Background Check
Clairissa H.
from
$22
per walk
5.0 out of 5 stars
6 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!

Profile image
Virginia B.
Sitter Profile Image: Somer S.
Verified Enhanced Background Check
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: Natalie H.
Verified Background Check
Natalie H.
from
$15
per walk
4.8 out of 5 stars
10 reviews
2 repeat clients
10 years of experience
Cambridge, WI, 53523

About: I love playing with and keeping dogs active and healthy, and love to treat them like they’re my own. I really like going for walks, to the park, or wherever it is that makes them smile and have fun! I have been taking care/sitting for various friends dogs for a few years, and for my moms dog since I moved out, whenever she needs help. I also had numerous dogs growing up, and have a puppy now! I am very flexible and eager to please, and I love to help anyone out to make their and their dogs lives easier/better.*while you’re on a fun vacation away, your dog will be on a fun vacation back home with me!* I teach September-June during the day so I can let out before and after work, and during the summer I am free all day long!! I always provide a gentle and calming presence when visiting a pet’s home. I want to make sure they are comfortable with my being there, so patience and calmness is something I find really important. Of course if they’re happy to play and get snuggles, I am happy and SO willing to do that too! That’s my favorite.

Sitter Profile Image: Allison B.
Verified Enhanced Background Check
Allison B.
Star Sitter
from
$22
per walk
4.9 out of 5 stars
38 reviews
5 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!!

Profile image
Dillon D.
Sitter Profile Image: Kelly L.
Verified Background Check
Kelly L.
from
$20
per walk
5.0 out of 5 stars
16 reviews
2 repeat clients
23 years of experience
Stoughton, WI, 53589

Raphael has a great run with Kelly. Got to see lots of pictures of his adventures. Kelly feed Raffi lunch for me as well this time. Followed all directions to a t! Highly recommended!!!

Profile image
Jillian M.
Sitter Profile Image: Joni V.
Verified Enhanced Background Check
Joni V.
from
$16
per walk
5.0 out of 5 stars
2 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: Brianna L.
Verified Enhanced Background Check
Brianna L.
from
$20
per walk
5.0 out of 5 stars
1 review
7 years of experience
Edgerton, WI, 53534

About: I'm a lifelong animal lover with years of experience caring for dogs of all breeds and sizes. I offer a safe, comfortable, and fun environment for your furry friend while you're away. Your dog will enjoy daily walks, playtime in my fenced yard, and lots of love and attention. I'm also experienced in administering medication and handling special needs dogs. Book a meet-and-greet today to see if I'm the right fit for your pup! Need a sitter with a schedule that fits your unique needs? I offer flexible pet care services tailored to your routine. Whether it's a last-minute trip or a regular commitment, I'm here to provide reliable, attentive care. When caring for pets in your home, I prioritize maintaining their routine and comfort. I follow your instructions closely for feeding, walks, playtime, and any other specific needs. I also provide updates and photos to keep you informed. My goal is to make sure your pets feel safe, loved, and stress-free while you're away!

Sitter Profile Image: Sheena V.
Verified Enhanced Background Check
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: Ava N.
Verified Enhanced Background Check
Ava N.
from
$22
per walk
5.0 out of 5 stars
2 reviews
10 years of experience
Stoughton, WI, 53589

About: I’ve been caring for animals for over 10 years, starting with in-home dog sitting as a teenager and continuing ever since. I have extensive experience with larger breeds, including German Shepherds and other high-energy dogs, and I’m very comfortable handling strong, active personalities. I’m also a Malinois owner, so I understand the level of structure, exercise, and attention that working breeds need. Whether your dog loves long walks, playtime, or just consistent, reliable care, I’m someone you can trust to treat them like my own. In addition to dogs, I’ve also provided in-home care for cats and am comfortable with a variety of temperaments and needs. I pride myself on being dependable, attentive, and communicative so you always feel confident your pet is in good hands. I am a part-tome firefighter/paramedic and have a fairly flexible schedule. I typically end up having a lot of days free especially this summer. Reach out with your needs and we can see what we can work out! I take safety and trust very seriously when caring for your pets. As a firefighter/paramedic, I’m trained to stay calm, aware, and handle unexpected situations quickly and responsibly. I always follow your pet’s routine closely, including feeding, exercise, and any specific instructions you provide. I’m attentive to behavior changes and make sure your pet is always secure on walks and in the home. I’m experienced with large and high-energy dogs, so I’m confident handling strong or reactive dogs safely. Clear communication is important to me, and I’ll keep you updated so you always feel comfortable and informed while you’re away.

Sitter Profile Image: Natasha W.
Verified Enhanced Background Check
Natasha W.
from
$20
per walk
3 years of experience
Cambridge, WI, 53523

About: Hi! I’m a college student at the University of Wisconsin–Stevens Point and a huge animal lover. I currently work in a doggy daycare and pet boarding facility, so caring for animals is something I do every day—not just as a hobby, but as a job I genuinely love.I have hands-on experience working with dogs of all sizes, breeds, and temperaments through my job in doggy daycare and boarding. This means I’m comfortable with: Handling multiple dogs at once Reading dog behavior and body language Managing high-energy and shy/anxious dogs Feeding routines and administering basic care I also come from a family farm, so I’ve been around animals my whole life and am used to responsibility, early mornings, and consistent care. I currently work part time as a CNA in Stevens Point. I’m looking for the opportunity to spend more time with animals whenever I can, as they are such a big part of my life. Personally, sitting in the clients home would work best for me, as I am a college student living with a few other roommates, which can be difficult for having pets here :)

Sitter Profile Image: Dayna V.
Verified Enhanced Background Check
Dayna V.
from
$25
per walk
5.0 out of 5 stars
17 reviews
4 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!

Profile image
Alixandria C.
Sitter Profile Image: Christine D.
Verified Enhanced Background Check
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: Laura O.
Verified Enhanced Background Check
Laura O.
from
$50
per walk
5.0 out of 5 stars
46 reviews
8 repeat clients
30 years of experience
Stoughton, WI, 53589

About: I’ve taken care of all kinds of animals my whole life, including my own, friends, and family’s pets. Through high school and college I volunteered at a rescue that specialized in cats. Most recently I worked at a county animal shelter as an animal caretaker. Through the shelter I have had training in handling and care of almost every pet imaginable, as well as extra training in dog behavior. I also have training in foster of special needs / challenging behavior dogs, as well as neonate kitten care. I have experience giving many types of medications as well as iv fluids. I am currently solely focusing on providing pet care, so it is very easy for me to adjust my schedule to accommodate whatever needs your pet may have. I will care for your babies in whichever way you want. In my home, my dog kids are allowed inside or outside whenever they want and are not kenneled. But I will do my best to be consistent with whatever schedule they are used to. I also enjoy jogging if your pup would prefer a faster paced walk.

Sitter Profile Image: Madigan U.
Verified Enhanced Background Check
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: Natalie G.
Verified Background Check
Natalie G.
from
$20
per walk
5.0 out of 5 stars
7 reviews
3 repeat clients
9 years of experience
Edgerton, WI, 53534

About: I have grown up with dogs, cats and pretty much any animal you can think of my whole life. I helped take care of a litter of 11 puppies ;1 day old up until they were all ready to go to their new homes. I can do baths, nail trimmings, walks you name it. I love dogs of all ages and breeds as I have a German Shepard so I have no fear of large dogs! I also have a Collie Spaniel mix so I am no stranger of high energy dogs. I have lots of dog sitting experience from house calls to over nights stays both at my house and theirs. I work full time and some remote but have flexibility in my schedule. I work full time but have flexibility in my schedule. I do not stay over night at your house or have animas come to mine but I do as many drop in visits as needed. I follow specific care instructions based on each animals need. I would tend to that animal the same way in their home or my own.

Sitter Profile Image: Elizabeth M.
Verified Enhanced Background Check
Elizabeth M.
from
$19
per walk
17 years of experience
Jefferson, WI, 53549

About: I had a German Shepard growing up and he was mainly my responsibility, taking him outside, feeding, walking, playtime. I currently have a senior cat that I've had since she was a kitten. I also have a male cat he's 5years old. I currently go to school part-time on Monday & Wednesday's, I have a part-time job as well that is very flexible and would give me all the time I'd like to help others with there pets. I love plants, making sure all my plants are pet friendly and everyone I safe. My living room is a good size to roll around and play. I have a patio if they wish to hang out side in the sun.

Sitter Profile Image: Trinity G.
Verified Enhanced Background Check
Trinity G.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
18 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!

Profile image
Gillian H.
Sitter Profile Image: Phillip W.
Verified Enhanced Background Check
Phillip W.
from
$30
per walk
5.0 out of 5 stars
21 reviews
8 repeat clients
23 years of experience
Stoughton, WI, 53589

About: I’ve had dogs in my life for as long as I can remember, and I currently have two of my own...Tripp and Lilly! Dogs are such an important part of my life, and I’ll care for your pup like they’re one of my own. I always go above and beyond to make sure dogs feel safe, loved, exercised, and happy while you’re away. Whether that means long walks, playtime, cuddles, or extra attention, I’m committed to providing the best care possible. I also have a reliable vehicle and can transport dogs to local dog parks if they need more exercise than a walk can provide or if you don’t have a yard available. I work full-time in Madison Monday through Friday during standard business hours, so I may not be the best fit for services that require potty breaks or walks during those times. However, I do occasionally have flexibility in my schedule and may be able to accommodate certain requests, so please don't hesitate to ask if I can make it work. My evenings and weekends are typically very flexible and available. If you have any questions, feel free to reach out. I’d love to chat and see if I’d be a good fit for your pup! :)

Sitter Profile Image: Laura Z.
Verified Enhanced Background Check
Laura Z.
from
$18
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
30 years of experience
Edgerton, WI, 53534

About: Hi! I’m Laura, a stay at home mom and lifelong dog lover who truly believes pets are family. Because I’m home full time, your dog will receive consistent attention, supervision, and loving care throughout the day. I offer boarding, daycare, and walks, and I’m comfortable caring for dogs of all breeds and sizes. I love going on walks throughout the neighborhood to give pups fresh air, exercise, and time to explore. Whether your dog is energetic and playful or prefers a slower pace, I’m happy to match their routine and individual needs. I have experience caring for both puppies and senior dogs and understand that each stage of life requires different levels of patience, structure, and comfort. My goal is to provide a safe, calm, and nurturing environment where your dog feels right at home. Why Choose Me? As a full time at home caregiver, your dog will never be left alone for long periods. I provide a loving, family style environment with daily walks, personalized attention, and plenty of affection. I also send regular updates and photos so you can have peace of mind knowing your family member is happy and well cared for. I look forward to meeting you and your sweet pup! Feel free to reach out to schedule a meet and greet so we can make sure it’s the perfect fit! I offer boarding, daycare, walks, and I’m comfortable caring for dogs of all breeds and sizes. I love going on walks throughout the neighborhood to give pups fresh air, exercise, and time to explore. Whether your dog is energetic and playful or prefers a slower pace, I’m happy to match their routine and individual needs. I have experience caring for both puppies and senior dogs and understand that each stage of life requires different levels of patience, structure, and comfort. My goal is to provide a safe, calm, and nurturing environment where your dog feels right at home.

Sitter Profile Image: Avery C.
Verified Background Check
Avery C.
from
$30
per walk
5.0 out of 5 stars
71 reviews
21 repeat clients
25 years of experience
Stoughton, WI, 53589

Avery was terrific! She was so patient and gentle with my two older pups. Her communication was outstanding and my dogs loved her. Thank you!!

Profile image
Lee E.
1 / 1
View more sitters

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

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.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer dog walking
  2. 2. Meet & Greet

    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

Sitters in Hillside average 3
repeat dog walking clients

FAQs for Dog Walking - Hillside

Frequently asked questions about Rover

As of July 2026, there are 1,714 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
  • 97% can help with giving oral medications or injections
  • 98% 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge