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: Anna B.
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Anna B.
from
$16
per walk
5.0 out of 5 stars
• 5 reviews
6 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: Kendra M.
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Kendra M.
from
$25
per walk
5.0 out of 5 stars
• 16 reviews
3 repeat clients
3 years of experience
Oconomowoc, WI, 53066

About: I have always had a deep love for animals and truly believe every pet deserves patience, care, and lots of love. I’m comfortable caring for all kinds of animals and will take the time to understand each pet’s individual needs, personality, and routine. Whether your pet is young, old, energetic, shy, or needs extra attention, I’m dedicated to providing them with the same love and care I would give my own!🐾😊 I love caring for animals and have for years! I don’t have a job currently so my schedule is completely free and flexible with any day and time:) I always make safety and trust my top priorities when caring for pets. I follow each pet’s routine and their owner’s instructions closely, while making sure they feel comfortable, loved, and secure. I provide a calm, clean, and safe environment and give every pet the individual attention and care they need!!

Sitter Profile Image: Sadie S.
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Sadie S.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 14 reviews
4 repeat clients
16 years of experience
Watertown, WI, 53094

“Sadie is so sweet and kind! She's great with my highly energetic dog, Scout. She walks him all around my neighborhood and is kind to all of our neighbors she meets on our walk. She's very dependable and has great communication skills. I am so glad I found her to help me with Scout!”

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Sandy G.
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 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: Emily W.
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Emily W.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
15 years of experience
Oconomowoc, WI, 53066

“Super easy to communicate with and reliable!:)”

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Elizabeth R.
Sitter Profile Image: Avery Z.
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Avery Z.
from
$18
per walk
9 years of experience
Hartland, WI, 53029

About: Hello! My name is Avery and I have been an avid dog lover my whole life! Growing up my family had a goofy golden doodle and a loving golden retriever that were staples to my childhood memories. Currently, my family has two Aussies (a black tri and red merle, incase you were curious!) both under the age of 2. These past two years I have been my family's personal dog sitter for when they go on vacations, weekend getaways, and casual late-night dinners. For those of you who may know, Aussies are an incredibly energetic breed, fortunately, I am young, strong, and ALWAYS looking for an excuse to be outside. I am capable of caring for all types of dogs through the well-rounded experience I have with not only the dogs within my family but my neighborhood as well. I have been tasked with walking, feeding, training, and bathing countless times, and I'm looking for my next friend for the summer! After graduating from the University of Wisconsin-Madison this past spring, I have A LOT of free time this summer before my full time position starts! Living in the Madison area for the past 4 years, I know it is incredibly important to keep an eye out for cars and pedestrians at all times while walking a dog. When my own dogs would visit my apartment I keep a tight grip on their leash while still allowing them to have fun and get their energy out. Luckily!! Im super familiar with the Lake Country area and have some personal favorite spots for walks!!

Sitter Profile Image: Taylor S.
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Taylor S.
from
$25
per walk
5.0 out of 5 stars
• 10 reviews
5 repeat clients
25 years of experience
Delafield, WI, 53018

About: I have been taking care of dogs and cats since I was 5, my sister is a vet and I always have access to ask her any questions if something were to ever happen, I hope to own my own hobby farm one day! I recently accepted a new nail technician position in Richfield, and my current work hours will be Monday 11 to 6, Friday 11 to 6 and Saturday 9 to 4 starting July 6th over time I will be adding in more days. Any questions please ask! For my own pets I have a fenced in yard for them, I wash there faces and paws everyday, I feed them and bath them. I follow any instructions given to me by a clients, weather its about dietary restrictions, exercise requirements, meds etc

Sitter Profile Image: Brenna C.
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Brenna C.
from
$30
per walk
5.0 out of 5 stars
• 4 reviews
17 years of experience
Summit, WI, 53066

About: Hey there! I’ve grown up with dogs and had lots of cats all of my life! I would be happy to help you out with your loved family members! I’m great with drop ins, as well as staying at your house for overnights. I have availability every day, except for Tuesday and Wednesdays. Please let me know if I can be of any assistance with your fur babies! ❤️ Pet care fits into my routine because I only work Tuesday Wednesdays. I don’t mind dropping in to say Hi to pets, let them out, or take them for a walk. I care for your pet as if they were my own💕 pets are part of our family!!!!! I have 2 dogs of my own which mean the world to us!

Sitter Profile Image: Nathan S.
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Nathan S.
from
$25
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
9 years of experience
Oconomowoc, WI, 53066

About: Hello, my name is Nathan. Your pet's safety is my first priority. I enjoy walking, spending time with, and caring for dogs and all animals. I have experience with going on walks and hikes with a variety of animals. I have a large yard with lots of room for exploration and play. There is a lot of nature and some nice ponds and trails nearby that are a lot of fun to walk around if your dog wants to do that. Also, there are many friendly dogs in the neighborhood that would love to play. I am available to house dogs or other animals too; I have room for two dogs of any size. Feel free to contact me if you have any special requests or questions.

Sitter Profile Image: Kirstin B.
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Kirstin B.
from
$35
per walk
5.0 out of 5 stars
• 8 reviews
1 repeat client
20 years of experience
Hartland, WI, 53029

“Kirstin is very committed to caring for her dog friends. Great communication and follow through!”

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Sarah F.
Sitter Profile Image: Allison S.
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Allison S.
Star Sitter
from
$32
per walk
5.0 out of 5 stars
• 57 reviews
21 repeat clients
3 years of experience
Sussex, WI, 53089

“Allison was very timely and professional. She was quick to communicate and had no issues with any changes of plans. We would recommend her to others and plan to reach back out to her in the future!”

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Julianna L.
Sitter Profile Image: Hannah S.
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Hannah S.
from
$20
per walk
5.0 out of 5 stars
• 136 reviews
5 repeat clients
4 years of experience
Menomonee Falls, WI, 53051

“Hannah was great! Took the time with our puppy and excited for her to walk him on a regular basis.”

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Bridget H.
Sitter Profile Image: Tia R.
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Tia R.
from
$38
per walk
20 years of experience
Delafield, WI, 53018

About: I have had pets my whole life. Currently I have 3 cats, 3 dogs, a hamster, and fish. I have also had bunnies, hermit crabs, and many reptiles. There is not an animal I don't love caring for or being around. I am good with animals of all ages and sizes!! I currently am a homemaker with an open schedule. I am available morning til night and overnights if needed. I have lots of time to spend with your pets! I care for every pet like they’re part of the family. I follow their normal routines for feeding, walks, playtime, medications, and rest, while giving them plenty of love and attention. I keep their environment clean and safe, and I make sure they get the exercise, enrichment, and companionship they need to feel comfortable and happy while you’re away.

Sitter Profile Image: Olivia K.
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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.

Sitter Profile Image: Travis H.
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Travis H.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 382 reviews
117 repeat clients
35 years of experience
Riverwest, Milwaukee, WI, 53212

“Travis did a very good job walking my dog Mikah while I was away. He is very friendly and my dog warmed up to him instantly. He was very persistent with the report cards and sending photos. Definitely would work with him again and recommend!”

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Shari S.
Sitter Profile Image: Emily M.
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Emily M.
from
$30
per walk
5.0 out of 5 stars
• 45 reviews
12 repeat clients
30 years of experience
Milwaukee, WI, 53213

About: I’ve been pet sitting for over 15 years and have taken care of pets twice that long. I’m a pet owner myself and currently training to be a Certified Vet Tech. Currently training to be a Certified Vet Tech so I have lots of experience with all kinds of breeds/types of pets. I have a flexible schedule to meet your pet’s needs! I own a car and am able to make it to jobs throughout the week. Happy to give your pet the care they need! I’m happy to play with pets, check in on them, let them out for potty breaks or walk them! I love the different personalities of pets and have a passion for animals (I’m a Virgo/earth sign and we love animals!).

Sitter Profile Image: Maxwell W.
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Maxwell W.
from
$20
per walk
5 years of experience
West Allis, WI, 53214

About: I’ve grown up caring for cats and dogs and have always enjoyed spending time with animals. I have an active dog of my own who loves going on long walks, so I’m very comfortable keeping energetic dogs active and entertained. As a high-level athlete, I’m active myself and genuinely enjoy being outdoors, whether that’s walking, playing, or simply spending time with a pet. I’ve also helped neighbors care for their animals while they were away. Right now I’m training in Milwaukee and have practice at 3:30 so I can take care of your pet during the day but also after practice if needed. Would be preferred if I did at the clients house but I live in a apartment right now they have a dog park and sorts.

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🙂

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

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  • 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.

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    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

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Popular requests for dog walking - Ashippun

Select a filter and find qualifying sitters offering dog walking.

Sitters in Ashippun average 3
repeat dog walking clients

FAQs for Dog Walking - Ashippun

Frequently asked questions about Rover

As of October 2026, there are 1,732 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 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 Ashippun 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 Ashippun. On Rover:

  • 88% of walkers can help with special care needs
  • 95% 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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