Dog Sitting Windsor
Book a Windsor dog sitter to watch your dog in your sitter’s home or yours.
Over 58 pet parents in Windsor have booked dog sitting
Windsor, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Lenys was amazing with my beagle. Very flexible and answered a last minute drop-in. She also sent updates and photos. Highly recommend her!! She will treat your baby like her own.”
“Erika was great! She was super accommodative and took care of our cats during the drop in visits. We also got a lot of cute photos of the cats while we were traveling. Highly recommend her if you're looking for a pet sitter !”
“Lynne was great and sent timely updates and took good care of our Kitties on a very short notice - she was friendly and quick and handled all items we asked of her and the pictures she took were very cute! Would book again!”
About: I’ve always loved dogs and genuinely enjoy spending time with them, whether that means going for a long walk, playing outside, or just keeping them company at home. I’m active and love being outdoors, so I’m especially happy to take dogs on walks and give them plenty of exercise and attention. I’m dependable, communicative, and will treat your pet and your home with the same care and respect I’d want someone to give mine. I’m comfortable following specific feeding, walking, and care routines, and I’ll always keep you updated while you’re away. I have a flexible schedule that gives me plenty of time to fit pet care into my week. I’m available for walks, drop-in visits, feeding, playtime, and check-ins throughout the week and on weekends. I’m happy to work with your pet’s normal routine and schedule! I know how important it is to trust the person caring for your pet and your home. I’ll follow your instructions closely and keep your pet’s normal routine as consistent as possible. I’m attentive, responsible, and happy to provide updates and photos so you know your pet is safe, comfortable, and getting plenty of attention.
About: I grew up with 3 cats and a golden retriever and am missing them since moving away from home! I’ve been watching my neighbors’ and friends’ cats for years — giving them pets, playtime, and all the cuddles they want. I also volunteer at Shelter from the Storm, where I help foster and take care of kitties in need. Whether your cat is super playful, a total lap cat, or a bit shy, I’ll make sure they feel safe, loved, and right at home with me! I work full-time but have good flexibility in the mornings, evenings, and weekends. This means I can easily do drop-in visits, walks, and overnight boarding on weekends. I’m usually available early mornings before work and evenings after work to care for your pets! I have a big yard where pets can safely play and explore. Your pet will get constant supervision, lots of playtime, and a calm, loving home environment. I can crate your dog if needed and will always follow your specific instructions.
About: I’ve taken care of animals since I was five years old. I’ve walked dogs since I was a child. I have had birds, gerbils, lizards, fish, cats, and dogs. My last animal companion was a rescued special needs Jindo dog from LA. I truly love all animals. I work for myself so my schedule is relatively flexible. I am available anytime with enough headway. Have car and can travel to clients. I can spend as much or as little time as your pet requires. I currently have no pets or housemates and a fenced in backyard for dogs. My house is safe and secure and situated in a quiet neighborhood. All furniture is pet friendly and accessible. Plenty of windows for cats to look out from.
“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! 🫶”
About: I have had pets since I was born. I grew up with dogs and a cat. I also have vet/daycare experience. I feel comfortable medicating if needed, and being around multiple dogs/cats at a time. I work full time, but I am free most Wednesday and Thursdays. For my own cat I typically play with him whenever I have free time. I make sure he gets good exercise because I know how important it is! I am patient with all animals. I know it can take time for them to warm up to new people. On walks I let dogs sniff around because that’s how they get the most enrichment out of it. Their walks are about them
About: Dogs control my life! By day I am a receptionist at a local vet clinic/rescue. At home, I have a rescue Chihuahua who is 8 years old and has been with me for 4 wonderful years. My whole day revolves around pets and I can't get enough. I'll treat your pets like the sweet baby angels they deserve to be! I work a later schedule most days of the week, Monday through Thursday I'm in the clinic until 7, and Fridays 9-5. I have plenty of time for morning and night walks, breakfast and dinnertime! I treat my clients home better than my own. You won't even know I was there! I'm clean, respectful and knowledgeable. I will stick with you and your pets daily schedules, so their routines don't get disturbed.
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.
“I have used Rissa in the past when I had changes going on and needed visits for my two dogs. Rissa came at very short notice. Provided photos. She is trustworthy and good.”
About: Hi! My name is Maricel I have a lot of experience with dogs with special needs and separation anxiety.I can give shots,fluids and medication. My two dogs unfortunately passed away had kidney failure So I have a lot of experience with that too. I work from 8 am untill 2-3 pm every day and I have free time after that. I'm free on weekends. Reach out to me and I can work around your schedule. Thank you! I don't have a fance yard but I'm sorrouned by parks that I will take them on walks or I can stay in your house where they will be in their environment. I will provide lots of love,walks and attention.
About: What sets me apart from other sitters is my personalized approach and extensive experiences with dogs and puppies. I have two dogs of my own right now one is a beagle and the other is a rescue. My family has had many dogs over the years including many labs and lab shelter mix which I have soft spots for. I also have a genuine love for animals and I love to take them for walks and play with them. I have dogsat for many different families and dogs over the past several years for both shorter times and extended periods of time from toy aussies to st Bernard’s and Newfoundland. I have experience with dogs of all ages, shapes, and sizes. I have helped to administer medications to pets when needed, helped with mobility, potty training, and providing comfort. I always make sure to create a loving, cozy, and playful environment where your pets feel safe, happy, and loved while you’re away! I am a nurse. I prioritize time management and plan my days to ensure I can dedicate quality time to pet care. Whether it is in the morning, evenings, or on the weekends I am happy to accommodate and find time for your pets needs. I will always try to make time and balance my responsibilities so that your pets receive the attention love and care they deserve. Your pets well-being is important to me, and I’m committed to providing them with consistent and reliable care. When caring for pets in my clients’ homes, I make sure to create a safe and comfortable environment where your pets receive feels right at home. I ensure there is a consistent routine, whether it is feeding times, walking, visits, playtime, etc. so your pet feels secure and happy. In your home, I’m careful to follow any specific guidelines you’ve set, ensuring your pets receive feels stays in their familiar environment with as much routine as possible. Whether it is providing fresh water, administering medications, or offering love and attention, I am committed to keeping your pet happy and healthy!
About: Many years of experience with family and friend pet care. I always have a great vibe with animals. I will treat your pet like family. I currently work 2 part time jobs The Madison Club downtown and Underdog Pet Rescue of Wisconsin. I do occasionally work weekend nights at one job. Times of availability may vary depending on the day of the week needed. If giving enough notice I can work around my schedule to help out. Thursday's I know my weekly schedule for the following week. I do have a fenced in back yard if any pets come over. Lots of room to run around. I live in a great neighborhood on the Eastside of Madison for walking any dogs. I will also sit and relax with your pet if that's what is needed. I like knowing all the things they love to do with you.
About: Pets bring us all kinds of joy and unconditional love. It's hard to relax on vacation or focus on an event with a piece of you missing . Be able to be present and ease your mind knowing another caring soul will show your pet the same love and attention they enjoy. I have 10 years of experience with all different breeds and sizes. I work remotely. My office is where the WIFI is the strongest. I have time to spend with animals. My children are grown leaving me with an abundance of free time Soft voices and lots of love and attention. Dogs I like to run and make sure that they have the exercise they need. Plenty of tug of war! Social cats I give lap time and bring a feather.
About: I grew up with dogs my whole life since then I have been taking care of my own, neighbors, friends and families fur babies too! I’m currently working from home but have flexibility. I am able to stop in throughout the day to assist with walks, potty breaks, and feedings too! Taking care of your dog is my main priority making sure to make their and your day go smoothly I will follow any directions that you’d like for your fur baby!
The median cost per visit for dog sitting in Windsor is $20
Dog parents share their Rover experiences - Windsor
Niyah and I appreciated the break up during the day to allow her get some free time. What an awesome service and Taryn was an excellent caretaker. She did an outstanding job caring for Niyah. The daily rover cards were proof as I could see the happiness. Thank again!
Book with peace of mind
- 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
Book and pay through Rover’s secured platform—no cash or checks required.
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. Search
Browse profiles of sitters near you who offer dog sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
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 $17 per visit as of November 2026. Most bookings cost between $8 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 November 2026, there are 1,392 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 Rover's Trust & Safety page.
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.
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 Meet & Greet.
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
- 92% 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 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 sitter.
Connect anywhere with the Rover app
