Dog Walking Windsor

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

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Over 35
pet parents in Windsor have booked dog walking

Windsor, 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: Taryn E.
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Taryn E.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
• 36 reviews
17 repeat clients
4 years of experience
Windsor, WI, 53598

“We've only had Taryn walking our golden retriever, Stark, for a couple of weeks, but it's already one of the best decisions we've made. It's been a huge relief knowing our dog is in great hands when we leave for work. Taryn is on time, great at communicating, and even goes above and beyond to do things such as bring in trash bins, Amazon packages etc. I highly recommend Taryn for any of your pet's needs.”

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Austin H.
Sitter Profile Image: Emily L.
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Emily L.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 43 reviews
14 repeat clients
25 years of experience
Sun Prairie, WI, 53590

“If I could give Emily a million stars I would! She was very communicative during her entire stay and sent SO MANY pictures!! Seriously, nothing made my day more at work than getting the picture of my dog AND kitties!! Very attentive to any need. I will always book Emily for future needs!”

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Ashley L.
Sitter Profile Image: Michel P.
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Michel P.
from
$24
per walk
5.0 out of 5 stars
• 80 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: Jackie G.
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Jackie G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 71 reviews
18 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
$25
per walk
5.0 out of 5 stars
• 13 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.
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Elizabeth K.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 54 reviews
23 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: Sarah W.
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Sarah W.
Star Sitter
from
$23
per walk
5.0 out of 5 stars
• 59 reviews
19 repeat clients
26 years of experience
Madison, WI, 53704

“Sarah took our 13 yo rescue dog for a walk which she really enjoyed. Sarah has taken care of our dog in the past for over night and has always been trustworthy.”

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Kathleen M.
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: Tiana B.
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Tiana B.
from
$30
per walk
5.0 out of 5 stars
• 32 reviews
13 repeat clients
5 years of experience
DeForest, WI, 53532

About: With years of experience in pet care, I go beyond just watching your dog - I create a personalized, fun, and safe environment tailored to your pet’s unique needs. Whether it’s daily walks, playtime, or cuddles, I offer a loving, attentive approach that ensures your dog feels right at home. Pet care is a natural part of my daily lifestyle. I plan my schedule around the pets I’m responsible for, making sure they receive consistent attention, exercise, and affection. For dogs, I build in time each morning, afternoon, and evening for walks, play, potty breaks, feeding, and enrichment. I’m active, reliable, and intentional about keeping them on their normal routine so they feel secure and cared for. For cats, I schedule dedicated visits for feeding, fresh water, litter box cleaning, playtime, and calm companionship. I’m patient with shy or independent cats and love giving extra enrichment to the social ones. I also create time for medication or special-care needs if required. I’m very routine-oriented, so adding pet care into my week fits naturally. Whether it’s multiple check-ins a day or longer stays, I make sure each visit is consistent, on time, and focused fully on your pet’s well-being. I create a safe space whether it be at my course or my client’s house by making sure they feel secure while also establishing a routine and sticking with what is familiar to them.

Sitter Profile Image: Morgan B.
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Morgan B.
from
$30
per walk
5.0 out of 5 stars
• 6 reviews
1 repeat client
15 years of experience
Bluff Acres, Madison, WI, 53704

About: I have been in the vet med field for about 7 years. During this time I have acquired many skills from that would set me apart from many other sitters. Hello everyone! I live a few minutes from Sun Prairie, although, I do work on the west side off of University Ave. I am typically available early morning or after working hours or on lunch breaks. I am also super flexible! We have 3 cats! I usually keep my pets in our finished basement during boarding stays. I am available for walks, potty breaks, meals/medications, and nail trims, at your request.

Sitter Profile Image: Jake D.
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Jake D.
from
$18
per walk
5.0 out of 5 stars
• 12 reviews
3 repeat clients
20 years of experience
Bluff Acres, Madison, WI, 53704

“Jake has been great! We have him recurring 2x per week walking our doggo, Matcha. At the meet and greet they got along great, matcha is a big puppy and loves to play. Jake takes him on nice long walks and reports anything unusual that we might need to know about matcha, (i.e. loose stool, etc.) He's great!”

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Holly N.
Sitter Profile Image: Ben K.
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Ben K.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 133 reviews
29 repeat clients
15 years of experience
Eken Park, Madison, WI, 53704

“Our Great Dane loves Ben. He has had great communication with us during all of his walks and has made sure that Bruno has “done his business” in the mornings. He is our favorite walker”

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Stephanie C.
Sitter Profile Image: Jess M.
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Jess M.
from
$20
per walk
5.0 out of 5 stars
• 37 reviews
6 repeat clients
1 year of experience
Waunakee, WI, 53597

“Jess kept me updated and sent a lot of photos of Boo. This was his first time having someone from rover come over and it went really well. Thanks!”

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Brian S.
Sitter Profile Image: Mary T.
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Mary T.
from
$20
per walk
5.0 out of 5 stars
• 14 reviews
3 repeat clients
4 years of experience
Marquette, Madison, WI, 53703

“Gives Mowgli lots of love and is so easy to communicate with!!!”

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Nancy 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: Lisa R.
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Lisa R.
from
$25
per walk
5.0 out of 5 stars
• 7 reviews
30 years of experience
Waunakee, WI, 53597

“Lisa was great with my lab and her puppy energy. She was great to work with - caring, attentive, and flexible”

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Andrea S.
Sitter Profile Image: Marcela M.
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Marcela M.
from
$23
per walk
5.0 out of 5 stars
• 1 review
4 years of experience
Eken Park, Madison, WI, 53704

About: Hi! My name is Marcela, and I’m a lifelong animal lover with a special place in my heart for both dogs and cats. I have two dogs of my own, Chester and Athena. Chester is my small rescue dog, and I’ve had him since I was 9 years old. I truly grew up with him, and he has been by my side for most of my life. Chester is deaf, and as he’s gotten older, he has also developed anxiety and takes medication to help manage it. Over the years, I’ve learned how important patience, consistency, and understanding an animal’s individual needs can be. I communicate with Chester using hand signals and gentle body language, and caring for him has taught me so much about connecting with animals at every stage of life. Athena is my pit bull, and we love spending time outdoors with our animals. Whether we’re going for walks, playing, or simply enjoying the fresh air, I genuinely love giving animals attention, exercise, and plenty of affection. Athena has also had difficulty getting along with other dogs, so we worked with her through training to help her become more comfortable and learn how to interact appropriately. This has given me firsthand experience with the patience, structure, and careful management that some dogs need when around other animals. I also have hands on experience caring for a cat with significant medical needs. My cat, Fergi, was diagnosed with HCM and eventually developed end stage heart failure. During his illness, I became very familiar with the day to day care that comes with heart failure, including administering medications, monitoring his breathing, appetite, energy, and behavior, and paying close attention to small changes in his condition. Going through that experience also taught me how difficult it can be to leave your pet in someone else’s care when they’re sick or have special needs. I know how much worry can come with wondering if they’re okay while you’re away. Because of that, I want to be the kind of person who gives another pet parent that same sense of comfort and reassurance, knowing their pet is being watched over with patience, love, and genuine care. I absolutely love cats, and after recently losing Fergi, I’m not quite ready to bring another cat into my home yet. I would, however, love the opportunity to care for and spend time with other people’s cats. It would be really special to have that connection again while giving your cat the love and attention they deserve. I also take pride in the everyday care I give my own pets, including brushing my dogs’ teeth daily. I’m happy to provide routine care like this when requested, along with walks, playtime, feeding, medication, and plenty of companionship. Whether your pet is young, a senior, anxious, shy, energetic, or needs medication or extra patience, I’ll treat them with the same kindness and attentiveness I give my own. I know how much trust it takes to leave your pets with someone, and my goal is for both you and your pet to feel safe, comfortable, and cared for while you’re apart. I can’t wait to meet you and your pets! ❤️ I have a flexible schedule since my partner and I run our own microgreens farm. This allows me to work pet care into my schedule and be flexible with walks, drop ins, and stays. I’ll care for your pet(s) based on their individual needs and any instructions you provide—every situation is different, and I’m happy to adapt to what’s best for them.

Sitter Profile Image: Hailey V.
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Hailey V.
from
$15
per walk
15 years of experience
Tenney-Lapham, Madison, WI, 53703

About: I’ve taken care of all kinds of dogs! Small or Big not a worry! I love being outside on a long walk but also don’t mind snuggling on the couch if needed!:) I do work a full time job but it’s quite flexible with being able to leave for them to be let out quick if needed! I’m free most days after 4pm and don’t start until 9am most days! I’m the kind of person to act like your dog is my dog! Only the best for your pets because I get it you want the best for them!:) I love to play and give scratches but I’m also willing to cuddle like I said !

Sitter Profile Image: Rebecca P.
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Rebecca P.
from
$27
per walk
5.0 out of 5 stars
• 8 reviews
4 repeat clients
10 years of experience
Middleton, WI, 53562

“Rebecca was great with Milo, on time, and provided detailed update on the walk. Will definitely want to hire her again.”

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Greg B.
Sitter Profile Image: Dakota P.
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Dakota P.
from
$20
per walk
10 years of experience
Marquette, Madison, WI, 53703

About: Dogs have been part of my life for as long as I can remember! I grew up with multiple family dogs, mostly larger breeds. After college, I adopted a dog of my own who was by my side for 10 wonderful years. I've also spent the past decade volunteering at local animal shelters, which has given me hands-on experience with dogs of every size and temperament, from tiny pups to gentle giants. Along the way, I've learned how to work with nervous or anxious dogs, administer medication, and care for the specific needs of senior dogs. Whatever your dog needs, chances are I've handled something similar. I can't wait to meet your pup and give them all the love they deserve! My schedule is very flexible, which makes it easy for me to work pet care into my day. My day job is fully remote, so I'm able to build walks and drop-in visits around my work rather than being tied to a rigid 9-to-5. Right now I have even more flexibility, since I'm between roles, so I can typically accommodate last-minute requests or visits at times that might be trickier for others to fit in. Since I offer drop-in visits, walks, and house sitting, I spend most of my time in your home rather than mine — so keeping things safe and familiar for your pet is my main focus. - I go over feeding, medication, and routine details with you before I start, so nothing gets missed - I double-check leashes, harnesses, and collars before every walk - I lock up and secure the house every time I come and go - I'm comfortable with nervous or anxious dogs — I read their body language and never rush them - I can manage medication schedules and give senior dogs the extra care they need - I send photo and video updates so you always know how your pup is doing - I keep your vet's info on hand just in case Your home, your routine, your dog — I just fold right in and keep things running smoothly while you're away.

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

Dog parents share their Rover experiences - Windsor

1 / 1
5.0 out of 5 stars

We've only had Taryn walking our golden retriever, Stark, for a couple of weeks, but it's already one of the best decisions we've made. It's been a huge relief knowing our dog is in great hands when we leave for work. Taryn is on time, great at communicating, and even goes above and beyond to do things such as bring in trash bins, Amazon packages etc. I highly recommend Taryn for any of your pet's needs.

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Austin H.
Dog Walking
5.0 out of 5 stars

Tricia has been wonderful with Cinco! We were a little nervous about hiring a dog walker for the first time, but Tricia immediately made us feel comfortable. She took the time to get to know Cinco, listened carefully to all of our instructions, and has been incredibly patient about letting Cinco set the pace and build trust with her. Cinco can be reactive to other dogs and can also be nervous around loud noises, so finding someone we trusted to walk her was very important to us. Tricia pays attention to her cues and adjusts the walk when Cinco is uncomfortable rather than pushing her. After only two visits, Cinco was already excited to see her! Tricia is also a great communicator and clearly cares about making sure both Cinco and we are comfortable. We feel very lucky to have found her and are looking forward to having her continue walking Cinco. Highly recommend!

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Kit S.
Dog Walking
5.0 out of 5 stars

Lensy takes Petey on such great walks! She’ll consistently communicate about how the walks go. Definitely look forward to her walking for us again!

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Kristalyn B.
Dog Walking
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
5.0 out of 5 stars

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.
Dog Walking
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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.
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Popular requests for dog walking - Windsor

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Sitters in Windsor average 3
repeat dog walking clients

FAQs for Dog Walking - Windsor

Frequently asked questions about Rover

The average cost of Dog Walking in Windsor is $17 per walk as of October 2026. Most bookings cost between $0 and $28 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 1,395 sitters on Rover offering Dog Walking across Windsor. 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 Windsor. 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 Windsor 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 Windsor. On Rover:

  • 88% of walkers can help with special care needs
  • 92% can help with giving oral medications or injections
  • 96% 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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