Dog Walking Hillside

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Hillside, Find top rated dog walking

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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

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

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

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

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

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

Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 54 reviews
22 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: 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.

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

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

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Zorba P.
Sitter Profile Image: Lensy A.
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Lensy A.
from
$25
per walk
5.0 out of 5 stars
• 17 reviews
7 repeat clients
15 years of experience
DeForest, WI, 53532

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

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

Sitter Profile Image: Cassie K.
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Cassie K.
from
$16
per walk
10 years of experience
Dousman, WI, 53118

About: I have 10 years of experience house/pet-sitting. I do the best I can to continue your pet's routine while you're away including watering/feeding, walking, playing, taking your pet on outings like the dog-park for example, admistering medications, cleaning up pet waste, or anything else you'd like me to do! I have experience taking care of all different kinds of pets such as chickens, ducks, fish, cats, dogs, hamster, hermit crab, turtle, and hedgehog. I also can provide overnight care for your pets including housesitting if needed. Housesitting responsibilites include watering plants, getting your mail, mowing the grass, putting out your garbage, or any other household tasks you'd like done while you're away including taking care of your pet and/or pets. I'm also available this summer Monday through Friday to drop-in to take care of pets from 1:30pm-6:00pm. This could include watering/feeding, walking, or anything your pet may need. I'd be happy to give referneces if needed. Thank you for considering me! I'm available all week to provide pet care in your home-drop in, overnight care, and house-sitting.Thank you for your time and considering me for your pet and home care needs! I do not offer pet care in my home, but can provide pet care in your home including drop-in/overnight pet-care in your home/house-sitting and I'd be happy to provide references if you'd like.

Sitter Profile Image: Natalina T.
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Natalina T.
from
$15
per walk
5.0 out of 5 stars
• 8 reviews
2 repeat clients
4 years of experience
Madison, WI, 53719

About: I’ve grown up with both dogs and cats and I love getting to spent time with them and get to know them. I’ve dog and cat sit before for neighbors before and have had the best time with their pets. I have a puppy of my own now and he is my best friend:) I am currently home and working a part time job in the morning so my schedule is pretty flexible. You can always message me about my availability. I currently am not having other animals staying over because we have a hectic house of three. I care for pets in my clients home based on their preference and my knowledge of what animals like most.

Sitter Profile Image: Devin V.
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Devin V.
from
$20
per walk
10 years of experience
Elkhorn, WI, 53121

About: I've had a love/passion for dogs since I was born into this life. Growing up, I've always had a dog in the house, so it easily became the norm for me. I have experience with a wide variety of breeds, including doberman, pitbulls, great dane, labs, boxers, beagles, and mutts. I truly love them all. I'm open to taking care of all breeds. I don't discriminate! One thing I will note is that I specialize in high energy/working dogs and am very familiar with larger breeds. Just to give you a quick example, I raised a Doberman from a puppy which led to me learning A LOT throughout the process. Doberman are a working breed and require plenty of mental and physical stimulation & I think I cracked the code! I’ve developed a deep understanding of what high-energy dogs need to thrive. I'm good at stimulating their minds, keeping them active and most importantly, happy. I'm not a certified dog trainer, but I do understand the importance of balancing their physical and mental well-being, and I'm dedicated to ensuring each dog has a great time with me! I'm very engaging and mindful, so whatever your dog may need, whether it's staying active outside or relaxing at home, I will do my best to provide. That's a promise. When it comes to availability, I am free at the moment. You can contact me any time and I will get back to you asap. I will make sure you feel comfortable with leaving your pets with me. To ensure you of this, I will send you daily photos & videos to show you how good of a time they're having! Also, you can give me a call ANYTIME. I know what it's like to drop my dogs off at a pet sitter's house, so my job is to give you the relief of knowing that your pets are in great hands. I can guarantee you this🙂

Sitter Profile Image: Olivia K.
Verified Enhanced Background Check
Olivia K.
from
$15
per walk
5.0 out of 5 stars
• 5 reviews
1 repeat client
5 years of experience
Beaver Dam, WI, 53916

About: I have grown up around cats and dogs my entire life. I enjoy spending time taking care of others. I am patient and compassionate, your pets well-being will be my #1 priority. I work part time as a CNA in a long term care facility. I am also attending college part time to purse a career in nursing. Over the years I have cared for numerous of my own cats and dogs. Simply by spending quality time with them every day, walking my dogs and cuddling with my cats. I know the importance of spending time with animals and I understand their basic everyday needs.

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

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  • 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 to book dog walking

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for dog walking - Hillside

Select a filter and find qualifying sitters offering dog walking.

Sitters in Hillside average 3
repeat dog walking clients

FAQs for Dog Walking - Hillside

Frequently asked questions about Rover

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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