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

Allison has been walking our dog Mila for almost a year now and we could not be happier with the services she provides. She does an amazing job with our very energetic pup, who absolutely loves it when she comes over to take her for a walk. Allison is incredibly professional and very easy to get in touch with. Each walk she gives me a detailed update on how things are going and anything that may have happened on the walk. If I had the option of giving her 10 stars I absolutely would!

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Carolyn C.
Sitter Profile Image: Taryn E.
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Taryn E.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
26 reviews
12 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: Heather S.
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Heather S.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
28 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: Michelle H.
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Michelle H.
from
$15
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
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: Carrie R.
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Carrie R.
from
$15
per walk
18 years of experience
Deforest, WI, 53532

About: I grew up on a farm and around animals my whole life. I’ve dog sat for many friends and family members of mine and would love to be able to look after yours. I work in the mornings and I am home by noon most days and am around all weekend to look after any pets. I go for long walks most days. I have a large, in fenced backyard and I am close to the park and walking trails. I also love to go hiking and would like to able to take dogs with too.

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: Samantha S.
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Samantha S.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
40 reviews
16 repeat clients
25 years of experience
Madison, WI, 53704

Samantha is amazing! Our puppy Mowgli loves her. She is very easy to communicate with, keeps us updated, and takes great care of our dog.

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Nancy L.
Sitter Profile Image: Elizabeth S.
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Elizabeth S.
from
$20
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
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: Jamie K.
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Jamie K.
from
$20
per walk
5.0 out of 5 stars
53 reviews
16 repeat clients
14 years of experience
Madison, WI, 53704

Jamie is awesome! She went above and beyond our expectations while taking care of our boys!! She is very professional and took the time to meet the boys before our scheduled dates with her. We got great pictures from her!! We will definitely be using her again

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Megan R.
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: Alyssa T.
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Alyssa T.
from
$23
per walk
5.0 out of 5 stars
79 reviews
19 repeat clients
10 years of experience
Sun prairie, WI, 53590

Alyssa was communicative, easy-going & respectful. My pup Popsicle felt relaxed around her & enjoyed her walks. Would definitely hire Alyssa again!

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Josephine D.
Sitter Profile Image: Tammy T.
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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 great with our energetic beagle/heeler mix!

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Vicki I.
Sitter Profile Image: Jackie G.
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Jackie G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
59 reviews
16 repeat clients
20 years of experience
Madison, WI, 53718

Jackie is consistent and punctual she treats our lalu as her own takes good care of him and gives him a good walk. Lalu really looks forward to her walking him

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Leo B.
Sitter Profile Image: Ben G.
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Ben G.
from
$21
per walk
5.0 out of 5 stars
12 reviews
2 repeat clients
35 years of experience
Madison, WI, 53718

Excellent service. He took care of our dogs like they were his own. I think they would have rather we stay on vacation and Ben come walk them. Will definitely use again.

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Rachel D.
Sitter Profile Image: Elizabeth K.
Verified Enhanced Background Check
Elizabeth K.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
37 reviews
10 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: Rachael D.
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Rachael D.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
15 reviews
7 repeat clients
10 years of experience
Sun Prairie, WI, 53590

She’s amazing!

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Trent K.
Sitter Profile Image: Jasmine W.
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Jasmine W.
from
$20
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
20 years of experience
Deforest, WI, 53532

About: I've always had a soft spot for animals, for years I thought I was a cat person- until I raised my first puppy. NOW I know that love, that dedication and pure joy. I've found something I love! I currently work from home two days a week and those days are flexible. I work in the office three days a week, 7a-4p. Available most weekends. I am aware of all surroundings and always keep my pooch or yours top priority. Long walks along the Yahara river and lots of visits to local dog parks.

Sitter Profile Image: Brenda S.
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Brenda S.
from
$20
per walk
4.9 out of 5 stars
31 reviews
10 repeat clients
9 years of experience
Waunakee, WI, 53597

This was the second time working with Brenda. She did a great job again. I received updates and pictures with every walk/ visit and medication was administered according to instruction.

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Cashton C.
Sitter Profile Image: Yee Lam C.
Verified Enhanced Background Check
Yee Lam C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
10 reviews
2 repeat clients
20 years of experience
Sun Prairie, WI, 53590

About: Hi my name is Yee Lam but everyone calls me Suki. I grew up with dogs and am a dog lover. I had a beloved toy poodle named Seven for 15 years, who was truly the best dog and a cherished member of our family. I’m a full-time mom, and when my son (9) and daughter (7) are in school, I have plenty of free time to care for pets—playing with them, feeding them, and giving them all the attention they need. My kids love dogs too, and I think this is a wonderful way for them to learn the joys and responsibilities of having a puppy. I’m available for boarding on weekends and most weekdays after 9 a.m. We have a spacious yard for safe outdoor play, and our neighborhood is calm, family-friendly, and right next to a school, with no major roads nearby, so you can feel at ease knowing your dog will be safe on our walks.

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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?

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  • 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 May 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 May 2026, there are 1,298 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, 83% 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 1,298 dog walkers in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 91% 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.