Dog Sitting Windsor
Book a Windsor dog sitter to watch your dog in your sitter’s home or yours.
Over 100 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.
“Jackie was a perfect fit for my drop in visits and day care. She was thorough in getting to know Apollo and his needs. She followed my recommendations and went above and beyond to make sure Apollo was taken care of, some people are just naturals when it comes to caring for pets, and I believe Jackie is one of them, 100/10 recommend!”
About: Hi! My name is Lensy, and I’m excited about the opportunity to care for your pet. A little about me: I am in grad school (online) and work a hybrid job which gives me flexibility/ allows me to be remote a good amount so your furry friend isn’t alone day! I have plenty of experience looking after neighbors’ pets, from playful puppies to full-grown dogs. I also have experience with birds and cats. I can’t wait to take your furry friend out for walks, keep them entertained, and meet their unique needs. I understand it can be hard to trust someone new with your beloved pet, so please don’t hesitate to share any concerns or specific instructions. I’m here to make both you and your pet feel comfortable! I’m flexible, understanding, and passionate about keeping pets happy and active. I look forward to meeting your little companion! PS you will see a lot of photos on my profile of my family golden doodle Coco, who is my whole world😌 I I often have the flexibility to work remotely and do grad school online which allows me to be quite adaptable. I am available to do in-person visits and check-ins throughout the day, though I’m unable to provide lodging. My weekends are currently free, so I’m happy to arrange care for your pets during that time as well. Please feel free to reach out to discuss how I can best accommodate your needs! When caring for pets in my home or in my client's home, I prioritize creating a safe, comfortable, and stimulating environment tailored to each pet's needs. In my client's home, I want to be sure to know their routines. I focus on providing a stress-free experience, ensuring your pet feels comfortable and cared for in familiar surroundings. At home, I have a pet of my own, a mini golden doodle named Coco, who has taught me a lot about pet care and the importance of personalized attention. I ensure a calm, pet-friendly space where all animals can relax and feel at ease. I also maintain consistency in feeding times, play sessions, and any special care routines. I always ensure their safety and well-being is my top priority, no matter the setting.
“Shatoria was so great with my cats. She is very responsive and a great listener. I had a lot of changes in care instructions, and she handled everything patiently and without any issues. She kept me updated, followed all the details carefully, and made me feel completely at ease while I was away. I could tell my cats were well cared for and comfortable with her. I would absolutely trust her again and highly recommend her to anyone looking for a reliable and attentive pet sitter.”
“My second time booking with Carley. She is an amazing pet sitter. Takes care of my boykitty like her own and is mindful of my place as well. Very professional and I highly recommend her when she is available. I dont need to worry to much if am away because she is reassuring me with amazing photos. I will book her again.”
About: I’m experienced with both cats and dogs, house sitting and plant sitting if needed. I have a senior cat myself and two other younger cats but I also grew up around dogs and love to dog sit and take dogs on walks when the weather permits. My schedule is usually very flexible. I’m a full time student and I’m working part time from home in the Miami area. As long as I have a solid Wi-Fi or data connection for a hotspot I’m good to go. If there isn’t already explicit instructions my usual schedule would be to walk the dogs every 2-4 hours (puppies more than that till their potty trained) and feed the animals as instructed. Cats and dogs both need their daily playtime as well. I’m willing to spend the night if you’d prefer or just come and spend the workday with them 12+ hours a day.
About: I grew up with dogs and miss having them in my life dearly! I have experience, walking, feeding and bathing dogs. I have experience with them all — from tiny schnauzers to giant goldendoodles that pull you along — and I would love to meet your furry friend! I have a full-time job so I’m available in the evenings and weekends for dog walking and visits. I could potentially take a calm doggo to work with me for pet sitting during the day, and I could also do early morning walks or visits when needed! When not in a fenced-in yard or dog park, I keep dogs on a leash to keep them safe. I can also adapt to your practices such as putting the dog in a harness, getting them into a crate, or closing certain doors when needed.
“Brenda took great care of my recently adopted feline, Atticus, when I was suddenly called out of town. I found her punctuality and dependability assuring, and her approach to providing care to a skittish kitty in alignment with mine; when I arrived home, Atticus was in great shape, physically and emotionally. Absolutely recommend her with enthusiasm.”
“Leah did a great job checking in on my cats while we were away. She was communicative, super nice, and followed through with what we asked. She sent lots of pictures of our cats when she checked in on them. When we got home, nothing was out of place and our cats had a clean litter box plus plenty of food and water. I definitely plan on booking Leah again in the future.”
“Christy did a great job with my cats! It was a very last minute trip and Chrissy responded to my request right away and followed all of my care instructions. Arthur and Zelda looked like they enjoyed their time with Chrissy!”
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!
“Kylie was absolutely wonderful with our cats, Georgie and Weezy!! She was punctual, attentive, and kept us updated with photos and messages during her drop-in visits. Georgie really liked her and she tends to be more timid with strangers. We’ll definitely book with Kylie again!”
About: Eric and Rachel share a love for their beloved Aussie-beagle Lilo and fostering rescue dogs together. We know that it is never easy to leave your beloved dog with someone new, and in a new place. As our own Lilo has struggled with separation anxiety before, we know how important it is to have a pet sitter who is present, patient, and able to cater their care towards a dog’s specific needs. Rachel has taken care of 6 different family dogs growing up, including a border collie, golden retriever, Boston terrier, 2 mixed breeds and a silky terrier. Eric has taken care of his family dog (chihuahua mix) since birth till now (11 years old). Together, we have fostered 16 rescue dogs these past two years, ranging from a high energy Great Pyrenees to 3 Border Collie puppies all at once, to a completely afraid and anxious Beagle mama and Shiba Inu mama that are recovering from very difficult situations. We have also looked after American pit bulls, a large Newfoundland, and senior doggies who have hip difficulties and special diets. Our own dog is a 3.5 year old Aussie-beagle, so we particularly love the herding dogs. :) We both have lots of experience working with dogs of all kinds of temperaments and needs, especially high energy dogs who require a lot of attention and care, and administering medication to dogs who have special needs. Rachel also loves cooking her home cooked meals for her dog, and can do that for yours too, if you need! We both work from home and have all weekends free. Our flexible schedules together allows us to bring dogs regularly on walks and to look after them consistently. We follow instructions really well, and can take care of your dog according to your requirements. We allow dogs to roam and sleep freely in our home, but we can also crate your dog easily if you prefer. We know how to work with your dog with lots of gentle care and love.
About: I have experience fostering cats and dogs of all ages the last 6 years. I have experience with special needs dogs and cats, reactive dogs, and puppy training. I work from 7:30-4 Monday-Friday I am available to stay at the house to be there in the morning for the pets. I will be there right after work. I unfortunately cannot watch pets at my place, but I can stay at your place or can just stop by to feed and let out.
About: I grew up on a farm and so I handled a wide variety of animals. I’m in nursing school and want a side hustle that I will enjoy doing. I can walk dogs Monday - Friday from 5:30 on. I have my own 2 Fur babies at home. One being a 2 year old boxer and the the other being a 3 year old mix. I know a lot about animals because I grew up with them. I have worked with a vet in Wisconsin a bit too so I know how to look for signs of sickness.
The median cost per visit for dog sitting in Windsor is $20
Dog parents share their Rover experiences - Windsor
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?
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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.
Meet local sitters who will treat your dogs like family
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
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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 on Rover is $18 per visit as of September 2026. Most bookings cost between $11 and $26 per visit. 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 September 2026, there are 1,398 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:
- 91% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 95% 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.
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