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
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: Lensy A.
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Lensy A.
from
$25
per walk
5.0 out of 5 stars
16 reviews
7 repeat clients
15 years of experience
Capitol, Madison, WI, 53703

Lensy is so wonderful! She’s consistently communicative and sends such fun photos. Absolutely incredible to have her care for Petey & shows above and beyond consideration for both my pets :) Look forward to having her walk again!

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Kristalyn B.
Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$22
per walk
4.9 out of 5 stars
48 reviews
8 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: Brianna L.
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Brianna L.
from
$20
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
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: Hailey M.
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Hailey M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
32 reviews
7 repeat clients
10 years of experience
Madison, WI, 53704

Hailey did a great job! She followed our instructions, and our dog rooster seemed to love her! Definitely will use her in the future and highly recommend!

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Rachael D.
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: Dayna V.
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Dayna V.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
20 reviews
5 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: Dawnlea W.
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Dawnlea W.
from
$15
per walk
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: Shatoria W.
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Shatoria W.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
35 reviews
12 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Shatoria was exceptional as a dog sitter for my pet. Being new to town, i reached out for recommendations and she totally lived up to her high praise. Big fan! Always on time and with proactive communication.

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Surya M.
Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
48 reviews
16 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: Baylee M.
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Baylee M.
from
$20
per walk
5.0 out of 5 stars
8 reviews
3 repeat clients
5 years of experience
Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53714

Baylee was awesome with my puppy dog, and my dog adored her. Very reliable, great communication, and she really did have my dog’s safety in mind while providing a fun and energetic walk. Highly recommended — will hire her again!

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David P.
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: 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, finish later in the afternoon so I am free later in the day. I enjoy being active, but always plan my schedule around pets to ensure consistent, loving care. 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: 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: Ginny H.
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Ginny H.
from
$25
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
30 years of experience
Sun Prairie, WI, 53590

About: I've had a fun-filled house with dogs and cats since I was in elementary school. I've worked professionally with pets as well, such as pet dental hygienist assistant, pet store associate and birthday party tour guide, and Chewy supervisor. I'm currently looking for opportunities to help out with pets of all sizes, ages, and abilities. I'm able to provide care to your fur baby all day. I can also devote nights and weekends to them! I have three dogs who are friendly. One has anxiety, so she keeps to herself mostly, but loves to snuggle with other dogs. I keep all foods and small items off of the floor, away from curious snouts. I have a fenced area in the back yard.

Sitter Profile Image: Jenn S.
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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: Julia S.
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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: Lynne O.
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Lynne O.
from
$20
per walk
30 years of experience
Oregon, WI, 53575

About: Animals have always been apart of my life in both big & small ways. Being able to care for other pets, is just an extension of me caring for my own. My goal is to make your pet(s) as comfortable, loved, and cared for as if you had never left. I pride myself in the small details & going above and beyond what is expected. ~ Experience with young puppies to senior dog, and diabetic dogs. Including giving insulin. ~ Extensive experience with cats including specialized medical needs. ~ Comfortable giving oral, topical, or injectable medications. MY BACKGROUND: At an early age while growing up on five acres in the country, I was often taking care of a variety of animals, including our dogs and many barn cats. I was a bit of a cat Momma, often times assisting with extra care like bottle feeding or treating illnesses as they came. Eventually I started taking care of our neighbors animals when they were away. Throughout childhood I had several special cats that became my indoor pets & my first adopted dog at the age of 13. After high school I worked at a stable. My ‘Cat Whisper’ abilities came in handy while here- tending to the cats & ensuring the kittens grew up & had a chance to be healthy, loved barn cats. As a young adult, I cared for my two indoor cats & my Boxer puppy - a dream come true. ADDITIONALLY: I have almost 10 years of experience as a CNA and have completed 1 year of nursing school. You can feel confident knowing that your pet is in capable hands. I’m currently working from home & homeschool my daughter, allowing my weekdays to be flexible. I’m also home most weekends. I’m available for house sitting, drop-in care, walks, and extended care. FOR THOSE LOOKING TO PLAN AHEAD… I have my Spring/ Summer 2027 currently unavailable as I don’t have enough information yet to determine my exact availability. If you have an upcoming trip you are planing and in need of care, or looking for reoccurring care during these dates, please message me directly to get priority booking as my availability opens. My goal is to make your pet(s) as comfortable, loved, and cared for as if you had never left, and to give you peace of mind while you’re away. I know that every family has a different way of caring for their pets. Therefore, I will work with you to find out how best to care for your animal by asking questions up front before I even step foot in your home. Communication is key. At the end of my visit, I will give you an overview of your pets time with me including sending pictures. If there’s anything else you’re looking for, just ask.

Sitter Profile Image: Ashley S.
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Ashley S.
from
$20
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
21 years of experience
Reeseville, WI, 53579

About: I have helped my family take care of our pets almost my whole life! Since moving out I’ve had my own pets (cats and dogs). I understand the importance of giving your pet attention while you’re gone, since they could be stressed with the change in routine! I’m a farm girl at heart! I’ve taken care of dogs, cats, horses, donkeys, sheep, ducks, chickens, cows, pigs, rats, hamsters….you name it! I work from home so I’m available to spend time with your pets throughout the day! As long as I have access to Wi-Fi I can work from anywhere! I am comfortable with crate training if your pet needs it. I follow direction very well so just leave me with a detailed note on how things run and I’ll keep it as consistent as possible for your pet!

Sitter Profile Image: Jimmy W.
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Jimmy W.
from
$25
per walk
5.0 out of 5 stars
24 reviews
7 repeat clients
25 years of experience
Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53704

Jimmy did amazing with Tucker! He took the time to come and meet the day before the walk to talk about Tuckers habits and dos/don'ts which made me feel really comfortable with letting someone else walk our dog. Tucker was extremely happy after the walk too!

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Spencer L.
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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 August 2026, there are 1,638 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
  • 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.

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