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.
“Blanca was amazing - super reliable and responsive! Our cat is usually grumpy, but Blanca is a natural and the cat LOVED her. Great updates and photos with each visit. Will definitely book again!”
“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!”
“Eric was warm and gentle caring for Cocoa. He was thoughtful and diligent to make sure he had everything he’d need to offer the best care. Will definitely book with him again. Thanks Eric!”
“Shatoria was absolutely awesome! She stopped in to check on my cat Olivine while my roommate and I were away for the weekend. During our initial visit, Shatoria asked a ton of questions about Olivine and her routine, some that I hadn’t even thought to bring up, which was great. During the actual visit, she passed along lots of photos of Olivine with her update. She also took a photo of her automatic feeder so I could see how Olivine had been eating, which I appreciated. I had never hired a pet sitter before, so that came with some anxiety, but Shatoria made me confident that I was leaving Olivine in great hands! I definitely know who to come to if we ever need any more help with Olivine in the future.”
“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.”
“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: 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.
“Kelsey was amazing with our new pupper and followed all the instructions asked of her. She and Osa had a great time and Kelsey was sure to send thorough updates and pictures as well. While Osa was very excited to see us that evening, she definitely made a new friend today!”
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.
“Carley is a delight and such a wonderful sitter! Incredibly sweet and a natural with animals, I had no worry at all leaving my pups in her care. Regular check-ins and photo updates throughout the weekend. I highly recommend Carley and will definitely try to book her again.”
“Leah and Jeremy were very friendly and professional during our meet and greet. Jeremy was great with communication on visit day and provided some great pics of the pups.”
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.
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.
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.
The median cost per visit for dog sitting in Windsor is $20
Dog parents share their Rover experiences - Windsor
This was my (and my girls’!) first time using the Rover app and Heather was outstanding! She was flexible and was able to accommodate my crazy schedule with time to meet my girls and see if their personalities were a good match. (Side note: they totally were.) I loved the details and the report card she left for me about the goings on of their adventures together. Thank you, Heather, for making my girls’ first experience amazing! 🩷
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.
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
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 Drop-In Visits - Windsor
Frequently asked questions about Rover
The average cost for Dog Sitting in Windsor on Rover is $18.32 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .
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.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Windsor stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
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 short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
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 calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Connect anywhere with the Rover app
