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

1 / 1
Sitter Profile Image: Allison B.
Verified Enhanced Background Check
Allison B.
Star Sitter
from
$22
per walk
4.9 out of 5 stars
54 reviews
9 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: Clairissa H.
Verified Enhanced Background Check
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!

Profile image
Virginia B.
Sitter Profile Image: Dayna V.
Verified Enhanced Background Check
Dayna V.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
23 reviews
6 repeat clients
25 years of experience
Stoughton, WI, 53589

Thanks Dayna! We appreciate you taking care of Sammy today. Thanks for giving him snuggles and love while it rained! He likes perfect weather and that’s about it lol. Glad you guys got out before it started raining ! Thanks again !!

Profile image
Alixandria C.
Sitter Profile Image: Eric C.
Verified Enhanced Background Check
Eric C.
from
$20
per walk
5.0 out of 5 stars
5 reviews
40 years of experience
Madison, WI, 53711

About: I’ve had dogs in my life since I was a child, primarily Labs. I walk for exercise and would love to have your dog along. I’m a travel RN not on contract so my schedule is wide open. I drive to Madison daily to workout so I can easily exercise your pets at your convenience. I only offer walking services at the moment. I will ensure that your pet is safe from traffic and other animals. I will treat them as my own.

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: Joni V.
Verified Enhanced Background Check
Joni V.
from
$16
per walk
5.0 out of 5 stars
4 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: JESSICA P.
Verified Enhanced Background Check
JESSICA P.
from
$30
per walk
5.0 out of 5 stars
16 reviews
4 repeat clients
20 years of experience
McFarland, WI, 53558

About: I will absolutely spoil and love your pets like they are my own! I am a recent graduate from UW-Madison in Wildlife Ecology where I gained animal experience. I also graduated from Madison College with an Associate Degree for Veterinary Technician. I worked in the veterinary field for over a year before attending UW-Madison. I take pride in my ability to care for animals and the love I have for them. My schedule is currently completely open to take care of and spoil all the pets I can. I have a Chocolate Labrador named Jake that would need to come with me when house sitting. He is good with dogs and cats. I might not have a fenced yard, but there is so much space near my apartment for dogs to play and run. There is also a trail close by that I have taken my dog on, which she loves. I have a truck that can transport them. If I am caring for pets in the client's home I have no issue with taking them out to play or on walks. I absolutely love being around pets.

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: Hailey R.
Verified Enhanced Background Check
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.

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: Rosana M.
Verified Background Check
Rosana M.
from
$25
per walk
5.0 out of 5 stars
10 reviews
2 repeat clients
10 years of experience
McFarland, WI, 53558

About: Hi, I’m Rosana! I am 24 years old and just graduated with a bachelors degree at UW- Madison! I joined Rover because I have always wanted to do a career that involves dogs! I have always loved caring for animals. Dogs are my favorites and I am always good with them. I have spent years caring for my grandparents dogs, neighbors pets, and family friends dogs. I have had a lot of experience with dogs of many ages and sizes. I am always ready to play outside and take your dog for long walks. I am always ready for the challenge! Thank you for choosing me to take care of your beloved pet! I am ready to play, watch, and care for your dog! :) :) I have currently quit my job. I do side jobs like DoorDash and rover. I create my own schedule so it fits in my routine very easy! I give a lot of attention to the animals. They are my main priority! I make sure my environment is pet safe and that they feel loved!

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: Jennifer E.
Verified Enhanced Background Check
Jennifer E.
from
$15
per walk
12 years of experience
Deerfield, WI, 53531

About: Hi! My name is Jenny. My family has always had dogs. I got my own puppy when I was 14, and trained himself through 4H. I showed dogs throughout my 4H career, training in agility and obedience. I'm a college student and am currently working towards a veterinary technician degree. I previously worked at a vet clinic and i currently work at a pet shop part time. I have helped take care of animals in the store, including puppies, kittens, birds, reptiles, and small animals. I have experience with animals of all sizes and ages, including dogs, cats, small animals, ferrets, rodents, birds, and reptiles. I currently take care of 3 dogs, 2 cats, ferrets, parakeets, a cockatiel, a conure, guinea pigs, rabbits, and chickens of my own. I work full time, but can take care of animals before and after work and on my days off. I work 10-6 weekdays in Madison. *I'm not able to board dogs/cats at my house, but I can board guinea pigs, rabbits, ferrets (must be utd on rabies/distemper), birds, some reptiles and other small animals/exotics* I can take care of any animals at your home. I can feed/water/walk or anything else that needs to be done. I can also take care of farm animals, including backyard chickens and other poultry, breeders animals, and can handle large amounts of animals.

Sitter Profile Image: Julia S.
Verified Enhanced Background Check
Julia S.
from
$20
per walk
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: Jenn S.
Verified Background Check
Jenn S.
from
$40
per walk
5.0 out of 5 stars
22 reviews
6 repeat clients
20 years of experience
Lake Mills, WI, 53551

About: I grew up on a horse farm and always had a variety of animals around me. A cat and dog were our constant companions, so caring for animals has always felt natural to me. As an adult, I realize that growing up that way taught me responsibility from an early age. I understand how important it is to have someone you can rely on and trust when you’re away from home, and I want you to feel completely at ease knowing your pets are in my care. When I care for your pets, I’ll follow their normal routines as closely as possible so they feel comfortable and secure while you’re away. I’ll give them the attention, affection, exercise, food, and care they need—and of course, I’ll clean up after them and leave your home just as I found it, if not better.

Sitter Profile Image: Trinity G.
Verified Enhanced Background Check
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!

Profile image
Gillian H.
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: Erika M.
Verified Enhanced Background Check
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: Cara H.
Verified Background Check
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: Evan T.
Verified Enhanced Background Check
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!

1 / 1
View more

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.

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

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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge