Dog Walkers in Windsor, WI

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

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Top rated Windsor dog walkers

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: Lexi F.
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Lexi F.
from
$15
per walk
5.0 out of 5 stars
6 reviews
6 repeat clients
17 years of experience
Windsor, WI, 53598

Lexi is very punctual and easy to work with. She takes great care of our pup and went above and beyond with extra requests today to get him some water and put him in his crate when they got back from their walk. Thank you, Lexi!

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Megan H.
Sitter Profile Image: Allison A.
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Allison A.
from
$15
per walk
5.0 out of 5 stars
129 reviews
31 repeat clients
25 years of experience
DeForest, WI, 53532

Be prepared for a very thorough prep meeting and detailed updates- like you may expect with a babysitter for a child. Allison wouldn’t be a good fit for someone who is looking for an especially quick key transfer; she takes this very seriously. She worked with my pup on reinforcing some of the training we were doing and communicated about her behavior in detailed notes. She definitely went above and beyond- exactly what you would want for your fur baby.

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Allison H.
Sitter Profile Image: Heather S.
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Heather S.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
31 reviews
4 repeat clients
25 years of experience
Windsor, WI, 53598

Heather is so good at communicating with me, she always watches for anything unusual in Josie’s routine and makes sure to notify me. She’s been very flexible and extremely reliable. As an anxious dog mom, I am so at ease knowing she is taking care of Josie. And Josie is always happy after her walk days with Heather!

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Morgan K.
Sitter Profile Image: Taryn E.
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Taryn E.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
27 reviews
13 repeat clients
4 years of experience
Windsor, WI, 53598

About: I have had pet care experience with a neighbor for four years now. And I have also helped own a dog for 8 years. With my neighbor I do pet sitting/drop in visits, dog walking, and cat care. With my own dog, I have had him since he was a puppy, and he is my best friend. I have had experience living with him, walking him, feeding him, and bathing and grooming him as well. I would do anything for my dog, and I will transfer that love to all animals I meet. I am a college student and my plan is to do this during my winter break between semesters. Since I will not have school during this time, my schedule is very free and flexible. I am doing this to have something to look forward to every day during break. So I am very open on a daily basis to accommodate to your schedule. My plan is to do services that are in my clients home because my dog right now doesn't always work well with others. So when I am in my clients home I will treat all people, items, and pets with the utmost respect and kindness. I will care for your pets on drop-in visits and on walks like they are my own.

Sitter Profile Image: Della H.
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Della H.
from
$15
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
3 years of experience
Windsor, WI, 53598

About: I have three months of clinic experience as well as almost two years of boarding experience where I work closely with all kinds of dogs and cats. I have also been pet sitting for many years including with puppies as young as two months, and kittens as young as six months. I currently work part time, but I am super flexible so please reach out if you have any questions about my availability. Pet care is my number one priority! I don’t offer in home services, since I live with my parents. However I am able to come to your home to either walk or watch your dog/cat!

Sitter Profile Image: Michelle H.
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Michelle H.
from
$20
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
23 years of experience
DeForest, WI, 53532

So great with my pups-love the pics she sent!

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Cecelia S.
Sitter Profile Image: delaney a.
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delaney a.
from
$17
per walk
2 years of experience
DeForest, WI, 53532

About: I have had experience watching dogs since I was 12. My neighbors often have me walk their dogs when they are unable, and about a year ago I started watching my family and friend’s dogs when they are out of town. I currently work part-time and I don’t have school during the summer so I am free most week days. I am also available on various weekends depending on my other job’s schedule. I create a safe environment in client’s homes by ensuring the dog has nothing dangerous within reach. Keeping a clean and safe space helps the both the dog and owner feel more at ease.

Sitter Profile Image: Maria & Bryan P.
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Maria & Bryan P.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
30 years of experience
Waunakee, WI, 53597

About: We have been loving and caring for dogs for a long time. Big and small dogs; young and old. Our son and 7 year old dog are welcoming I am currently working from home and Bryan works part time. Our son is home schooled at this time, therefore, we have time and energy to help other dogs and other families We have a large yard in a quiet neighborhood; part of our yard is fenced and other part is open for additional exercise. We also walk our dog daily.

Sitter Profile Image: Milan R.
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Milan R.
from
$15
per walk
10 years of experience
DeForest, WI, 53532

About: Hi! My name is Milan, and I am a dependable, caring, and responsible pet lover. I have experience caring for dogs, cats, and other pets for family, friends, and neighbors. I am comfortable feeding, walking, playing with pets, administering basic care, and following specific instructions to keep your pet happy and safe. As a CNA, I am detail-oriented, trustworthy, and used to providing compassionate care. I understand how important pets are to their families and will treat your pets like my own while you’re away. I have a very flexible schedule and am available most days, including weekdays, evenings, weekends, and holidays. Pet care fits easily into my daily routine, allowing me to provide plenty of attention, playtime, walks, feeding, and companionship. I am happy to accommodate different schedules and can often accept last-minute bookings when needed. Your pet’s safety, comfort, and happiness are my top priorities. I carefully follow all instructions regarding feeding, medications, exercise, and routines. I provide regular updates and photos so you can feel confident while you’re away. Whether caring for pets in your home or during walks and drop-in visits, I will treat your pet like family and ensure they receive loving, reliable care at all times.

Sitter Profile Image: Elizabeth S.
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Elizabeth S.
from
$20
per walk
5.0 out of 5 stars
8 reviews
2 repeat clients
9 years of experience
Madison, WI, 53718

About: I am a huge dog lover. I love all kinds of dogs and have grown up with all different kinds of dogs of varying size and temperment. My family has had 2 havanese dogs and 2 newfoundlands so I have experience with a variety of sizes. Recently, I lost my soul dog, Max. Max was a shepherd mix and was my whole world. My husband and I had Max since he was a puppy and are looking to get our dog fix by helping out others. We understand the stress finding care for your dog can create, and we would love to help provide a safe and fun environment for your dog when you need it. We have a large yard (unfenced) and safe neighborhood for walks. We also have 2 children, aged 5 and 3. I am a stay at home mom, so I am available most of the time from home any given week. I have 2 children, aged 5 and 3, and they would love to help care for and love on a doggy. I have a large, unfenced yard in a quiet, safe, and dog friendly neighborhood. Our dog Max was always free to run around the yard without any issues. Dogs are allowed inside, on our furniture and I still have Max’s dog bed for use as well. I am also happy to pop in by your house to walk your dog if that’s needed.

Sitter Profile Image: Samantha S.
Verified Enhanced Background Check
Samantha S.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
47 reviews
18 repeat clients
25 years of experience
Madison, WI, 53704

Great with my Cane Corso's. They love their walks.

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Ernst G.
Sitter Profile Image: Michel P.
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Michel P.
from
$24
per walk
5.0 out of 5 stars
79 reviews
31 repeat clients
30 years of experience
Sun Prairie, WI, 53590

Michel is so nice! She came over a few days before to meet me and talk about the dog walking I was hiring her for. The walk went great an she sent me pictures which I appreciated. She is very professional I will definitely be asking her for more services in the future!

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Julie D.
Sitter Profile Image: Krista I.
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Krista I.
from
$15
per walk
5.0 out of 5 stars
7 reviews
5 years of experience
Sun Prairie, WI, 53590

About: I've always had pet dogs and cats since childhood. At this time my husband and I are unable to have a pet of our own, but I frequently house sit and watch pets for friends and family. I work as a school counselor, so I have plenty of availability during the summer to care for your fur-buddies! I am energetic and enjoy playing with excited animal friends, and I also hold firm boundaries and can support your training. I work at a school, so I have plenty of time over the summer to love and care for your pets! I teach summer school from eight to noon a few weeks over the summer, and I also teach occasional yoga classes, but besides those commitments, my time belongs to the fur-babies! I am very energetic and happy to go for long walks or play with dogs to tire them out! I am also clean and detail-oriented so I will take good care of your home if you are away. During the school year I work as a school counselor so I value service to others, honesty, integrity, and sharing joy and kindness.

Sitter Profile Image: Rachael D.
Verified Enhanced Background Check
Rachael D.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
23 reviews
7 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Rachel is fantastic!

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Trent K.
Sitter Profile Image: Alyssa T.
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Alyssa T.
from
$20
per walk
5.0 out of 5 stars
81 reviews
19 repeat clients
10 years of experience
Sun prairie, WI, 53590

Alyssa was easy to communicate with and great with our dog Cora. She took her for a cold walk in the snow while we were at work and left a detailed review with photos as well which is always appreciated!

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Jordan F.
Sitter Profile Image: Erika M.
Verified Background Check
Erika M.
from
$21
per walk
4.9 out of 5 stars
163 reviews
77 repeat clients
13 years of experience
Sun Prairie, WI, 53590

Erika is great! She was very prompt in replying to my inquiry and very accommodating for a day visit on Thanksgiving! Lucy took to her right away! It was welcoming to know Lucy was in good hands and was calm and relaxed when I returned. We're looking forward to having Erika come again!!

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Cheryl J.
Sitter Profile Image: Brandi V.
Verified Enhanced Background Check
Brandi V.
from
$20
per walk
8 years of experience
Windsor, WI, 53598

About: I’ve been dog sitting for a couple years now. I’ve had experience from little to big dogs. From a basenji, labrador, german shepherd, great pyrenees mix, a yorkie, and a few other breeds! Friends rely on me to exercise, feed, and give attention to their fur baby. 😊 I have plenty of time on the weekends! I’m currently available at any time Friday-Sunday to take care of your sweet pets! Can start at any point of the day or night! I take care of pets as if they were my own! 🥰 I care about their safety, what they eat, who comes around them, how much outside time they get. I promise to take care of them and give them all the attention. I want to be able to give them some love and snuggles while watching some tv. I make sure to stick to their food schedule and like to let them out every 2-4 hours. Daily exercise is important to me, I like to go on walks and can always use a walking buddy! 🐶

Sitter Profile Image: Tammy T.
Verified Enhanced Background Check
Tammy T.
from
$30
per walk
5.0 out of 5 stars
10 reviews
5 repeat clients
13 years of experience
Deforest, WI, 53532

Tammy was wonderful and we will absolutely ask her to walk our pups again!

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Eric E.
Sitter Profile Image: Jade R.
Verified Enhanced Background Check
Jade R.
from
$15
per walk
2 years of experience
DeForest, WI, 53532

About: Hello! My name is Jade, I am a freshman in college at UWW. I have watched my neighbors, friends, extended family, and even co workers dogs before. I trained the dog that I have now and even some puppies. I absolutely love animals (especially dogs). I can feed them, take you dog out on walks, train, play with them, and get them to settle down. I am a very loving and extroverted person so it will not take me long to get to know your animal. I am hoping to start soon so if you are interested or have any more questions message me! I’m available for morning dog walks on Fridays, Saturdays, and Sundays. On Mondays, I’m free in the morning as well. During the week, Tuesday through Thursday, I’m available for walks in the early afternoons before 4 PM. I treat every dog like my own. Whether I’m staying overnight to keep them comfortable in their own home or popping in for a walk, I focus on making them feel safe, happy, and loved. I’m attentive to each dog’s routine, energy level, and quirks—ensuring they get personalized care.

Sitter Profile Image: Wystria C.
Verified Enhanced Background Check
Wystria C.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
10 years of experience
Ridgewood, Madison, WI, 53704

Wystria does a great job!

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Trent K.
1 / 1
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Over 19
pet parents in Windsor have booked dog walking

Windsor dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Lexi was amazing at accommodating us for a last-minute additional walk this week! She's very responsive and great to work with, and she loves our pup!

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Megan H.
Dog Walking
1 / 1
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How Rover works

  1. 1. Search

    Read verified reviews and choose a dog walker who’s a great match for you and your dog
  2. 2. Meet & Greet

    Meet either virtually or in-person with a walker to discuss the level of care needed for your dog
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 dog walker has to cancel, we’ll work with you to find a new walker.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Windsor average 3
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Windsor on Rover as of Jun 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Windsor dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 1,334 dog walkers in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 82% of Windsor dog walkers respond in under an hour.

Dog walkers in Windsor have an average of 15 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Windsor.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 1,334 dog walkers in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 90% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.