Dog Walking Ashippun

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Ashippun, 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: Natalie K.
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Natalie K.
from
$14
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
12 years of experience
Oconomowoc, WI, 53066

Was great!l and fast response!!

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Natalie H.
Sitter Profile Image: Amanda C.
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Amanda C.
from
$20
per walk
30 years of experience
Neosho, WI, 53059

About: I have had pets all my life. I have 5 of my own dogs of various shape and size and foster for a couple different rescues! I am very flexible, I'm available most of the time and love to meet new pets. I try to fit the needs of pet owners where I can. I don’t plan on doing any home care. I have 5 dogs of my own and also foster. This just isn’t possible at this time.

Sitter Profile Image: Cooper B.
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Cooper B.
from
$18
per walk
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Hartland, WI, 53029

About: I've been taking care of all types of animals for several years. Including snakes, lizards, cats dogs, and even a tarantula. I've provided exercise, care and the same love I have for my animals at home. I care daily for my own two cats, and work part time as a pet/ house sitter. Please check with me for my upcoming availability. I can rearrange my schedule to suit your needs. I will take care of your animal's needs with attention and care. Whether that means following a special meal plan, going on ten walks a day, or anything else they require. I’m happy to provide references from past clients. If you ever have any questions or concerns, feel free to call or text me anytime. My phone is always open to you.

Sitter Profile Image: Regan R.
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Regan R.
from
$13
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
7 years of experience
Hartford, WI, 53027

About: As a dog owner myself, I understand how important it is to trust someone with your pet. Each animal deserves love and care! I've cared for dogs of all ages, sizes, and personalities, ensuring they get the attention they deserve. I treat every pet like my own and prioritize safety, patience, and communication with the owners! I currenty works nights as a waitress and spend my days staying active and doing online college. My days are super flexible for your furry friends! I will treat your fur babies as if they're my own! Safety is the most important thing as well. I can follow any directions and send updates and pictures to put your mind at ease!

Sitter Profile Image: Brendan B.
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Brendan B.
from
$10
per walk
2 repeat clients
1 year of experience
Hartland, WI, 53029

About: I'm comfortable with feeding, administering medications, and walks for dogs and cats. I understand how important it is to follow each pet's routine and making them feel safe and comfortable while your away. I'm flexible and available for any time of the week, including weekends. I'm happy to work with your schedule for drop-ins, walks, and extended care. When caring for pets in homes, I treat your space with respect and follow your instructions carefully. I stick to your pet's regular routine for feeding, walking, potty breaks, and playtime to keep things consistent and stress free.

Sitter Profile Image: Ella W.
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Ella W.
from
$14
per walk
5.0 out of 5 stars
3 reviews
10 years of experience
Oconomowoc, WI, 53066

My pup absolutely adored Ella! She was so excited to see her and just wanted to play and play. Ella gave me lots of picture and video updates and I could tell she treated my pup just like she would her own. Super easy to get along with a took great care of my baby!

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Julia M.
Sitter Profile Image: Bayli M.
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Bayli M.
from
$16
per walk
5.0 out of 5 stars
1 review
1 year of experience
Oconomowoc, WI, 53066

About: Hi! 🐾 I’m a teacher with summers off and a lifelong animal lover. As a dog mom myself, I know how important it is to have someone you trust caring for your pets. Whether your pet needs walks, playtime, cuddles, or dropin visits, I’ll make sure they feel safe, loved, and well cared for while you’re away. I can’t wait to meet your furry family members! 🐶🐱💕 During July, I teach summer school, so I’m available anytime after 12 PM for walks, drop-ins, and pet care. In August, my schedule becomes much more flexible, allowing for additional daytime availability. Once the school year begins, I’ll primarily be available on weekends and for evening/late-night care. As a teacher and animal lover, I enjoy spending my free time caring for pets and making sure they get plenty of attention, exercise, and love. I treat every pet like my own! I maintain routines, provide loving care, and create a safe, comfortable environment where pets feel happy and cared for while their families are away.

Sitter Profile Image: Katelyn W.
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Katelyn W.
from
$15
per walk
5.0 out of 5 stars
29 reviews
13 repeat clients
8 years of experience
Oconomowoc, WI, 53066

Katelyn is great with our dog. I appreciate her fitting us into her schedule and coming to walk him while we’re away at work.

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Marissa P.
Sitter Profile Image: Ramsey S.
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Ramsey S.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
53 reviews
12 repeat clients
40 years of experience
Oconomowoc, WI, 53066

Ramsey is fantastic! She was able to watch our 2 month old puppy on short notice and gave us updates every day. Will definitely be booking with her again!

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Lyndsay L.
Sitter Profile Image: Raegan S.
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Raegan S.
from
$25
per walk
5.0 out of 5 stars
2 reviews
9 years of experience
Oconomowoc, WI, 53066

About: I’ve take care of dogs my whole life. I’ve taken care of puppy’s to senior dogs. I groom, clean up, and shower them in love I work part time but have a bunch of free time to take care of dogs. I am commuting to college so when school starts but I still have plenty of time to take care of dogs I always show dogs love and give them space when needed. I have two dogs and many more before that, so I have experience with dog behavior

Sitter Profile Image: Shay H.
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Shay H.
from
$20
per walk
5.0 out of 5 stars
22 reviews
10 repeat clients
25 years of experience
Summit, WI, 53066

Shay is absolutely amazing! My only request is don’t book her because we need her… j/k not kidding… seriously 200% puppy approved satisfaction!

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Sy S.
Sitter Profile Image: Anna B.
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Anna B.
from
$16
per walk
5.0 out of 5 stars
2 reviews
2 repeat clients
18 years of experience
Oconomowoc, WI, 53066

My baby absolutely adores Anna and she’s been so good about sending pictures while on their walks and been 10/10 with communication. Absolute gem of a find we love her!!!

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Julia M.
Sitter Profile Image: Brooke G.
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Brooke G.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
29 reviews
2 repeat clients
20 years of experience
Oconomowoc, WI, 53066

About: We recently moved back to our roots to a spot right off South St. In Oconomowoc. We had our dog sitting business in San Diego, CA and will miss our furry friends so much! My husband and I both love animals very much and have the perfect set-up to host. We enjoy morning and evening cuddles and allow dogs on the couch and bed :) We will take care of your pup just the same as we care for our own. We have a 4 year old mutt that we adopted 3 years ago who has brought so much joy to our life! She loves to play and enjoys the dog park/hanging around other dogs as much as she can. She loves walks around the lake as I am sure your pup will too! We both have experience taking care of other dogs and have dog sit for many of our friends and family members for extended periods of time when they are out of town. We can provide pictures as little or as often as you would like. Excited to meet your furry friend soon! I currently work 4 days of the week and have every Thursday off. My husband works remotely from home so he is able to tend to your pups needs all day. This schedule works great for our pups that need frequent potty breaks and attention. We have long leashes attached to our back deck so the dogs can enjoy the sun and being outdoors as much or as little as they would like without having to worry about them wandering off! Moxie loves basking in the sun and shade out there as I am sure yours would too! Water bowls always provided and refreshed as needed.

Sitter Profile Image: Emma R.
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Emma R.
from
$20
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Pewaukee, WI, 53072

About: I've lived with animals my entire life. Growing up, we had five dogs, four cats, bunnies and guinea pigs, snakes and lizards, fish, and chickens. Currently, while living at home in the summers, we have snakes, lizards, spiders, a cat, and three dogs, one of which is mine. My dog Winston is a service dog in training that my mom and I are owner-training. While I'm in no way a professional trainer, I can help with teaching or maintaining the basics with any dog. I'm currently home for the summer from school and waiting on an application for a part-time job. I am free most of the day right now, as I haven't started working yet. So, I can come over and take care of any pet's needs most any time. I can take care of your animals' needs any time, whether it's taking them on a walk, letting them outside, feeding, cleaning up, or playing with them. My dogs at home are crate trained, so if your dog also stays in a crate at certain points of the day or night, I can easily crate them.

Sitter Profile Image: Cindy S.
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Cindy S.
from
$28
per walk
5.0 out of 5 stars
51 reviews
14 repeat clients
45 years of experience
Oconomowoc, WI, 53066

Cindy is reliable and great with our dogs!

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Gina R.
Sitter Profile Image: Anna H.
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Anna H.
from
$25
per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
12 years of experience
Oconomowoc, WI, 53066

Anna took the best care of Winston! Our puppy can be shy and nervous, but she treats him like one of her own regardless and we are so thankful to have her spend time with him while we are at work. Thank you again Anna!

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Kristen M.
Sitter Profile Image: Roger W.
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Roger W.
from
$25
per walk
5.0 out of 5 stars
41 reviews
14 repeat clients
30 years of experience
Hartland, WI, 53029

About: A little about me - I grew up in the area. As a child we always had a dog and a cat in our home. So from a young age I felt like I had a knack for understanding pets and training them. I even trained my last cat to sit, lay down, and play dead like a dog. Friends would come by to film him with their phones doing the tricks because they said their friends didn't believe it was true. Unfortunately he passed away a few months ago. I am recently re-semi-retired. So this is a great way for me to keep busy, get some exercise, and enjoy some pet time since I lost my little buddy. Also, because I am semi-retired I can spend all of my time (other than occasionally ducking out for a fish fry or an errand) with your pet. They won't be locked in a crate for 8+ hours while I'm at work. I hope you and your family are healthy and safe. Feel free to contact me with any questions :)

Sitter Profile Image: Jenna S.
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Jenna S.
from
$30
per walk
4.7 out of 5 stars
19 reviews
6 repeat clients
16 years of experience
Oconomowoc, WI, 53066

About: About Me: Hello! I’m Jenna. After taking some time off to focus on early motherhood, I am thrilled to be back on Rover offering house sitting, drop-in visits, and dog walking! I hold a BA in Corporate Communications and Human Resource Management from UW-Whitewater and work remotely for my corporate job. Because my office goes wherever my laptop goes, I can provide flexibility, frequent check-ins, and daytime companionship for your pets right in the comfort of their own home. My Experience & Specialties: Animals have been a part of my life since day one. I grew up on a farm surrounded by dogs, cats, cows, and pigs, and spent years fostering puppies. Over my 15+ years of pet care experience (including 6 wonderful years on Rover). I have also cared for a few farm animals such as horses, donkeys, goats, and chickens! Whether you have a household pup, kitty, or a small hobby farm, I have the hands-on experience to keep everyone happy and fed. Home Care & House Sitting: When house sitting, I treat your home with the utmost respect. I am highly organized, clean, and detail-oriented. I’ve done this plenty of times and am always happy to handle extra tasks like watering your plants, bringing in the mail, and keeping your space tidy while you are away. Note: Back at my own home, I'm a proud mom to an 8 year old cat named Bear and a toddler. For drop-in visits and walks, my toddler might occasionally tag along in a stroller, so I love working with pets who are comfortable and friendly around kids! I can't wait to give your pets the best care possible. You can travel with total peace of mind knowing your home and your fur babies are in excellent hands! I work remotely, which gives me the opportunity to be there whenever for your pet. I can be present caring for your dog all day while working from my laptop from home! I have a cat at home. She is very spoiled. She enjoys her cat tree watching birds outside and her many naps. I’m home all day every day usually so she gets plenty of attention. While Dogsitting working from home will allow me to provide the best attention and care for your pets!

Sitter Profile Image: Malia K.
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Malia K.
from
$20
per walk
10 years of experience
Oconomowoc, WI, 53066

About: Hi there! My name is Malia, and I’m a dedicated dog lover ready to care for your furry friends as if they were my own. With a reliable, caring, and energetic approach, I ensure your pup gets the attention, exercise, and love they deserve while you’re away. Whether it’s long walks, playtime, or cozy companionship, I customize my care to match your dog’s unique needs and personality. I’m experienced with dogs of all sizes and energy levels, from playful puppies to senior companions. Why choose me? • Flexible availability to fit your schedule • Passionate about creating a safe and happy environment for pets • Plenty of outdoor activity and cuddles guaranteed Let’s chat to discuss how I can help you and your pup! I am a stay at home mom who is raising a beautiful baby boy ! Easy to make my own schedule! Always can be home! I am always watching the dogs, when outside must be on a leash and being watched as well! When inside always entertained and monitored throughout the day

Sitter Profile Image: Amber P.
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Amber P.
from
$40
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
28 years of experience
Oconomowoc, WI, 53066

About: I have grown up with all kinds of animals, dogs being the main one. Love carin for dogs and always making them feel loved, even when owners may have to be away. What better way to spoil your pet then to make sure they have a great day too! I am the kind of person that would go to a party and hang out with the dog. I have excoerience in caring for both people and animals and hope that I may be able to help care for more. I will always be focused on what you are looking for for your dog and making sure that they get the time and love they deserve each day. Hope to talk to you soon. ? ❤️ We are a working household but have staggered start and end times so very little time is left alone. During that time dogs can remain out if possible or can be crated. Our dogs are crate trained for this time as well, though not always done. We have two friendly, though large dogs to keep yours company. We also have 2 cats, but can be placed in a different area of the house as needed. Have 2 meal times per day and can adjust to fit needs. Always have water available and frequent outside time.

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

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Popular requests for dog walking - Ashippun

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Sitters in Ashippun average 3
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FAQs for Dog Walking - Ashippun

Frequently asked questions about Rover

As of August 2026, there are 1,793 sitters on Rover offering Dog Walking across Ashippun. 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 Ashippun. 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 Ashippun.

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 Ashippun. 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.

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