Dog Sitting Windsor

Book a Windsor dog sitter to watch your dog in your sitter’s home or yours.

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Over 104
pet parents in Windsor have booked dog sitting

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Sitter Profile Image: Tucker S.
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Tucker S.
Star Sitter
from
$18
per visit
4.8 out of 5 stars
• 15 reviews
3 repeat clients
10 years of experience
Orchard Ridge Community, Madison, WI, 53711

About: I have had dogs since my childhood and have worked with breeds of different sizes and backgrounds, including some with special needs. In my home life, I have two cats that I adore and spend much of my free time with. I’m available all day on weekends, as well as from 5:30pm onward on weekdays (typically). If you have specific requirements for your animal let me know and we can create a schedule that works best for you! I can perform any specific needs that your pet may need. One of my own pets has special medical requirements, so I am familiar with taking care of animals that need extra care.

Sitter Profile Image: Anne F.
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Anne F.
from
$15
per visit
5.0 out of 5 stars
• 2 reviews
20 years of experience
Sun Prairie, WI, 53590

“Anne was very responsive and arrived as requested. Maizie looked happy in the check in pics and was in good spirits when I got home.”

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Paul H.
Sitter Profile Image: Jenna M.
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Jenna M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 8 reviews
3 repeat clients
10 years of experience
Capitol, Madison, WI, 53703

“Helped out during a family emergency. Very responsive and followed directions perfectly. I highly recommend her for drop in care!”

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Maggie A.
Sitter Profile Image: Alexandra H.
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Alexandra H.
from
$20
per visit
5.0 out of 5 stars
• 10 reviews
1 repeat client
5 years of experience
Madison, WI, 53704

“Lexy is a true dog lover. Nina warmed up to her right away. We felt totally comfortable having Lexy stop in for a drop in visit. She kept us update on her visit. Looking forward to using Lexy again to take care of Nina.”

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Sherie H.
Sitter Profile Image: Autumn P.
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Autumn P.
from
$20
per visit
5.0 out of 5 stars
• 11 reviews
2 repeat clients
15 years of experience
Middleton, WI, 53597

“We're very pleased with Autumn, and greatly appreciated her above and beyond services for our 2 cats, AND the stray barn cats from abandoned property next door! During the meet/greet they were on our deck, as it was the time I usually feed them, and Autumn eagerly offered to fill their bowls while she was here. Our request was for only 2 cats, she didn't have any obligation beyond that. THAT'S above and beyond! Thank you, Autumn! We'll reach out again when we're away next time! 🫶”

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Paula W.
Sitter Profile Image: Abigail A.
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Abigail A.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
• 16 reviews
2 repeat clients
17 years of experience
Middleton, WI, 53562

“We had a great experience with Abigail taking care of our two senior dogs over Memorial Day weekend! She was communicative, prompt, and consistently checked in when questions came up. We really appreciated her flexibility and willingness to accommodate our dogs’ individual needs and quirks. It gave us peace of mind knowing they were in reliable and attentive hands while we were away. We’d absolutely book with her again!”

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Brittany H.
Sitter Profile Image: Louisa S.
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Louisa S.
from
$35
per visit
5.0 out of 5 stars
• 9 reviews
3 repeat clients
15 years of experience
Heistand, Madison, WI, 53714

About: I’ve taken care of animals since I was a young girl occasionally pet sitting around the neighborhood. Now, I am an avid animal lover. I have years of volunteer experience at the Dane County Humane Society where I care for a variety of animals. I have experience caring for animals with diverse medical needs. I am a geriatric social worker in Dane County. I have most holidays off, but am available after 4pm during the work week. I am also available over the weekends for pet care. I believe that trust is essential in a petsitter. I will provide frequent updates, pictures, and videos of your pets as well as try my best to accommodate to specific requests.

Sitter Profile Image: Kiley O.
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Kiley O.
from
$14
per visit
18 years of experience
East Buckeye, Madison, WI, 53716

About: i’ve taken care of all kinda of animal, dogs, cats, and others! i’ve been taking care of many animals all of my life big or small☺️ i’m currently working a full time job, so I am required to either work after 10 pm and before 1pm during the day anytime between☺️ I have three cats all inside we groom them very regularly and feed them two times a day, we make sure to keep them stimulated and exercised so they live a long life!

Sitter Profile Image: Marcela M.
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Marcela M.
from
$27
per visit
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: Alliyah D.
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Alliyah D.
from
$18
per visit
5.0 out of 5 stars
• 10 reviews
3 repeat clients
2 years of experience
Wexford, Madison, WI, 53717

“Alliyah watched our 15 y/o dog for 12 days while we were on spring break. She was easy to schedule with and communicative. Georgie seemed to really enjoy her visits and we recommend her!”

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Paige N.
Sitter Profile Image: Dakota P.
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Dakota P.
from
$20
per visit
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.

Sitter Profile Image: Grace K.
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Grace K.
from
$15
per visit
10 years of experience
Fitchburg, WI, 53713

About: I've had 2 family dogs and 4 cats! As well as helping take care of friends and roommates pets. I love them and it's fun for me, just thought it'd be a cute and easy way to make a little extra money. I work full time so can only do quicker drop-ins in the mornings and/or evenings during the week but could drop by more over weekends! Am good to drop by homes/apartments and feed/walk/hang out with pets for a bit, not available to care for them from my apartment.

Sitter Profile Image: Robin B.
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Robin B.
from
$50
per visit
4.4 out of 5 stars
• 15 reviews
5 repeat clients
35 years of experience
Madison, WI

About: I have raised and trained dogs (cats, bunnies, & livestock) since a very young age. I am very active and love to run and play with critters. But I also love to chill and snuggle. I have farm experience, and spent some time working with dog breeders, groomers, and in animal healthcare. I have experience with dogs of all ages, sizes, and breeds. I have experience pet sitting for friends, family, and neighbors since I was a child. I have dealt with special needs, injuries, administering medication, and holistic health remedies. I understand that dogs require a considerable amount of attention and exercise, and I am up for the challenge. I am a professional business owner and I take my responsibilities to you and your pets very seriously. I am a small business owner so I get to make my own schedule. It allows me to break up the work day and pop in on pups. Every dog loves a mid day walk in the park! We have a fenced in yard and we take daily walks around the neighborhood. Our dogs are the biggest divas and have ALLLLLL the toys and treats and chews that a pup could dream of. (And backyard games of fetch to run off all those extra snacks)

Sitter Profile Image: Raven H.
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Raven H.
from
$40
per visit
4.9 out of 5 stars
• 11 reviews
4 repeat clients
5 years of experience
Madison, WI, 53704

“She was sooo amazing!! Could not have asked for a better sitter and peace of mind. Updates and pics and communication was great. Will definitely be using her again if she's willing and available.”

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Tracy P.
Sitter Profile Image: Sidney R.
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Sidney R.
from
$20
per visit
5.0 out of 5 stars
• 85 reviews
33 repeat clients
20 years of experience
Middleton, WI, 53562

“Sidney was so professional work with, and we appreciated her responding to us so quickly when we needed help on short notice. Layla loved her! We will definitely use Sidney again.”

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Brian K.
Sitter Profile Image: Travis M.
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Travis M.
from
$30
per visit
5.0 out of 5 stars
• 24 reviews
5 repeat clients
15 years of experience
MONONA, WI, 53713

“Travis stepped up at the last minute to provide drop in care over the holidays. He was communicative, great with Frankie, and very professional. We came home to a very happy pup!”

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Zayna T.
Sitter Profile Image: Milanne D.
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Milanne D.
from
$25
per visit
19 years of experience
Blackhawk, Middleton, WI, 53562

About: I’ve been around and taken care of dogs of every kind my entire life basically. Neighbors, friends and family have relied on me since I was a little girl to walk, feed and bathe their pets. I currently dog sit full time, so I’ll have plenty of time to play with your pups! I’m available for boarding all seven days of the week at anytime of need! I have a spacious yard and two friendly female dogs(both spayed) to keep your fur baby company. I can easily crate your dog if needed.

Sitter Profile Image: Kendra B.
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Kendra B.
from
$35
per visit
30 years of experience
Glendale, Madison, WI, 53716

About: I grew up with dogs, cats, and horses, and have experience in oral med administration with both cats and dogs. I have a soft spot for the big dogs (they're lap-sized if you commit!). I run half marathons so getting good exercise in will be no problem (even in Wisconsin weather!). I'm currently training for distance running, so you can expect great exercise for your pet! Whether it's a long meandering sniff-ari or an intense loop around the neighborhood, I would love to know what fits your dog best. As I'm in your home, your instructions are paramount. You know your pet better than anyone, and I am happy to keep their normal routines in place. I like getting to know each animal and their unique personality, and while I *love* giving snuggles and pets, I understand some pets prefer their space.

Sitter Profile Image: Miranda M.
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Miranda M.
from
$20
per visit
5.0 out of 5 stars
• 3 reviews
20 years of experience
Deerfield, WI, 53531

About: I am a loving, compassionate, and reliable person that has a love for animals. I am also athletic and can take your puppy companion for a jog! I have unlimited availability for pet care. The only time I am not available is at 3pm, when I pick up my two pet loving children from school. I have a fenced in yard in a nice neighborhood, and a lake across the street if your pet likes to swim. I am also available to come to your home as well. I am available in Rock County and Dane County.

Sitter Profile Image: Kylie E.
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Kylie E.
from
$25
per visit
5.0 out of 5 stars
• 12 reviews
6 repeat clients
20 years of experience
Stoughton, WI, 53589

“Kylie was a life saver taking a last minute appointment request. She was great with both of our cats for in-home visits. She went above and beyond with the quality of service provided. Would definitely use her as a sitter again.”

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Tracy L.
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The median cost per visit for dog sitting in Windsor is $20

Dog parents share their Rover experiences - Windsor

1 / 1
5.0 out of 5 stars

Heather did an exceptional job caring for our very active golden retriever. She is timely and loving! 💕

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Julie L.
Drop-In Visits
5.0 out of 5 stars

We had daily drop in visits with my dog and she was always there on time and gave Odin such great care. I would absolutely use her services again.

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Ryan H.
Drop-In Visits
5.0 out of 5 stars

Kelsey was great with our dog and his drop-in visits! I appreciated her flexibility with my visit time changes and her communication was awesome. I loved the pictures she included in her updates! Would definitely book her again

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Kristina J.
Drop-In Visits
5.0 out of 5 stars

Peyton was awesome with our puppy Luna! She let us know what they did, kept us updated, and even took her for a walk during our drop in visit. Would recommend and have her come again!

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Jenna G.
Drop-In Visits
5.0 out of 5 stars

Tiana has done such a good job letting our puppy out for her lunch time breaks and walks!! We trust her completely and are so happy we found her!

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Jenna G.
Drop-In Visits
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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.

Why Choose Rover?

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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.

How to book dog sitting

  1. 1. Search

    Browse profiles of sitters near you who offer dog sitting.
  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 sitting - Windsor

Select a filter and find qualifying sitters offering dog sitting.

Sitters in Windsor average 7
repeat dog sitting clients

FAQs for Dog Sitting - Windsor

Frequently asked questions about Rover

The average cost of Dog Sitting in Windsor is $19 per visit as of October 2026. Most bookings cost between $11 and $27 per visit. On Rover, sitters 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 1,373 sitters on Rover offering Dog Sitting across Windsor. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Windsor choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter 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 .

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.

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 sitter 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 sitter 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 sitter for longer stays or first-time bookings. Read our tips for your first .

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Windsor with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Windsor. On Rover:

  • 89% of sitters can help with special care needs
  • 93% can help with giving oral medications or injections
  • 94% 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.

sitters 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 sitter.

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