Dog Walking Windsor

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

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Over 27
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
• 32 reviews
15 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
• 45 reviews
8 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
$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: Emily L.
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Emily L.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 39 reviews
14 repeat clients
25 years of experience
Sun Prairie, WI, 53590

“Emily was wonderful to work with. She was very flexible and loved my dog. She did what I asked for her to do with my dog. This was my first time using Rover 🐾 and I will definitely use it again because of my experience with Emily.”

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Dona G.
Sitter Profile Image: Jackie G.
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Jackie G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 68 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: Lensy A.
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Lensy A.
from
$25
per walk
5.0 out of 5 stars
• 16 reviews
7 repeat clients
15 years of experience
DeForest, WI, 53532

“Lensy is so wonderful! She’s consistently communicative and sends such fun photos. Absolutely incredible to have her care for Petey & shows above and beyond consideration for both my pets :) Look forward to having her walk again!”

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Kristalyn B.
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: 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: Tricia D.
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Tricia D.
from
$22
per walk
5.0 out of 5 stars
• 1 review
2 repeat clients
14 years of experience
DeForest, WI, 53532

“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.
Sitter Profile Image: Hailey M.
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Hailey M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 45 reviews
11 repeat clients
10 years of experience
Madison, WI, 53704

“Hailey did a great job! She followed our instructions, and our dog rooster seemed to love her! Definitely will use her in the future and highly recommend!”

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Rachael D.
Sitter Profile Image: Mira D.
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Mira D.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
• 10 reviews
3 repeat clients
10 years of experience
Waunakee, WI, 53597

About: As a pet owner myself, I understand how important it is to trust the person caring for your fur babies. I currently have my sweet girl Nova at home and am comfortable with pets of different temperaments and needs. I strive to create a safe, stress free experience while keeping owners updated with lots of photos and messages. Whether your pet needs playtime, cuddles, medication, or just a consistent routine, I’ll make sure they receive attentive care. I’m currently a SAHM with a very flexible schedule, allowing me to provide reliable care and accommodate a variety of pet care needs throughout the day. Your pets are treated like family! I have 1 cat in my home currently that is okay with dogs that visit. I maintain a clean, safe, and pet-friendly environment and carefully supervise interactions at all times.

Sitter Profile Image: Erika M.
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Erika M.
Star Sitter
from
$23
per walk
4.9 out of 5 stars
• 147 reviews
80 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: Emilee K.
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Emilee K.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
11 years of experience
DeForest, WI, 53532

About: I am an aspiring vet student who has 10 plus years of experience with cats and dogs both owning and sitting for. I have medical knowledge that other sitters may not have as I work at an ER for pets as a nurse! I am extremely flexible with my time and availability and will ensure that your pet gets the well-deserved love and care they need! As a bonus, I can offer nail trims, sanitary shaves, and ear cleanings during their stay if requested! I'm currently working part time night-shift, so I will have plenty of time to play with your pets! I make my own schedule during the day, so I can easily work around your pet's needs. I have a dog and cat myself at my apartment that are well socialized to be around other dogs. I can accommodate up to two dogs in my apartment if needed and can also go to your home if preferred. For cats, I find it best to go to them. I do not have a yard, but my apartment complex is pet friendly with a play area and lots of walking trails nearby.

Sitter Profile Image: Ben G.
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Ben G.
from
$25
per walk
5.0 out of 5 stars
• 12 reviews
2 repeat clients
35 years of experience
Madison, WI, 53718

“Ben was great with my large standard poodles. He did a previsit and asked a lot of good questions. He knew how to slowly earn their trust. Ben sent pictures and updates from each visit. He also administered medication. We will definitely have him care for them again.”

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Jean L.
Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 52 reviews
20 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: TAYLOR P.
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TAYLOR P.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 43 reviews
17 repeat clients
15 years of experience
Madison, WI, 53704

“Taylor was very kind with Kora and let her take out her frisbee, which she loves to play with in the afternoons.”

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María Paula 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: Jordan F.
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Jordan F.
from
$22
per walk
5.0 out of 5 stars
• 1 review
1 repeat client
10 years of experience
DeForest, WI, 53532

About: Hello! My family and I currently have a beautiful silver Laborador Retriever, Mae, who brings so much happiness and energy to our lives. I’m a firm believer that a house is not a home without a furry friend! I have a pretty flexible schedule during the day, and would love to help out some pet owners in need of anything from short potty break, midday play, or walk while you’re out! I’ve grown up with dogs my entire life and am super comfortable with pets of all ages and sizes and have a lot of experience, including caring for older pups who might need a little extra TLC. I also have experience caring for cats (including those who have medication needs). Looking forward to hearing more of your pet care needs and meeting some new furry friends!

Sitter Profile Image: Yee Lam C.
Verified Enhanced Background Check
Yee Lam C.
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.

Sitter Profile Image: Donovan S.
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Donovan S.
from
$15
per walk
18 years of experience
Sun Prairie, WI, 53590

About: I've had dogs every year of my life. Moved around the country with them, and taken care of them like family since before I could walk. I've taken care of all ages. I'm currently working part time to help put me through college, so I have plenty of time most days to come in and take care of your dogs. I know how to make sure your dogs is safe and taken care of, and will follow any instructions about how you specifically want things done. Everyone does things differently, and I want to try and keep their habits as similar to normal as possible.

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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

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

Taryn was so great walking our puppy! She was on time, was great with communicating and took Luna for a great walk around our neighborhood. We can’t wait to have her in the future!

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Jenna G.
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
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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • 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.

Why Choose Rover?

  • Cashless payments

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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.

  • World-class support

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

Meet local walkers who will treat your dogs like family

  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

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for dog walking - Windsor

Select a filter and find qualifying sitters offering dog walking.

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 on Rover is $17 per walk as of September 2026. Most bookings cost between $0 and $28 per walk. 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 September 2026, there are 1,420 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 a map of the walking route , 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 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 Windsor. 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 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 Meet & Greet .

walkers on Rover set their own cancellation policy , 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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