Dog Sitting Windsor
Book a Windsor dog sitter to watch your dog in your sitter’s home or yours.
Over 19 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.
About: I have experience with all kinds of dogs of all sizes. I have owned 3 pitbulls so I for sure know how to handle dogs that size. I also have a park near my house that is very discrete where the dogs can come roam around. It is fenced and barely anyone ever goes to. I used to bring my dogs over there when I had them. I am available full time if needed. I work from home. I can do pick up & drop as well. Please let me know, it would be my pleasure! I care for the dog as if they are my own. I know animals can become family, just as mine have became family. I will go accordingly to your dogs schedules and make sure they have the best care.
About: I’ve had dogs/cats since I was little so not only am I used to taking care of my own pets but other peoples pets as well. I am used to feeding, letting out/walking, and playing with dogs that are not my own. I can walk/ let out pets/ feed pets any day of any time I need to. I work from home and have a flexible schedule, so stepping out to let your pets out or to visit them is no issue! I have a fenced in yard and can let dogs out to potty/run around or take them to a dog park! I give them as much time as they need to be outside and move!
“Laura has provided such loving care for our pets, particularly our senior cat. I am so thankful I found her and will continue to utilize her services going forward. I highly recommend her!”
About: I have owned 5 dogs, 2 cats and 10 chickens over the past 40 years and provide service in Naples, FL, Marco Island and Bonita Springs. I am available most days in Naples FL, but very flexible depending on your needs. Do not hesitate to call me, I can give your pup the time and love he deserves. I would prefer to come to your home, only because my home is not fenced in, but could keep the dog on a leash at all times outside
About: At home I've been taking care of Ramsey, my small, high-energy, dog for almost 9 years. In these 9 years I've gained a larger a sense of responsibility and my love for animals has grown tremendously. I know how to communicate with dogs and read dog body language in order to cater to their needs and give them best care. As a recent graduate, I have more flexibility in my schedule, I can dedicate ample time to caring for my pets. This includes feeding, grooming, walking, and spending quality time with them to ensure their well-being and happiness. Engaging in activities like playing, training, and companionship not only enriches their lives but also brings a sense of purpose to my day. While job hunting, I find solace and a sense of responsibility in taking care of my pets, creating a positive and fulfilling routine amidst my current situation. At home I make sure my dog cannot access anything that can harm him. I close doors to the bathroom so he can’t access the trash can and I put gates up around the house to areas he can’t be in. During walks I am very careful and aware of my surroundings. If I walk at night, I walk in a well lit area with a few friends.
“I had a day trip into the city and needed someone to stop by my house to take the dogs out and be with them for a short period of time. Thankfully Joanna was able to help out and allowed me to be gone for most of the day. Nice to have someone who is responsible and can be trusted. Thanks again Joanna!”
About: My career training makes me hyper aware of my clients needs whether they be human or animal. I can meet them where they are physically and mentally and cater to their needs. My work is flexible so my schedule can fit your pet's routine. I typically do my workout in the early morning which leaves the remainder of the dedicated to your pet's priorities. When I'm with your pet/s they are my priority whether it's feeding, walking, playing or just cuddling. I love animals but can't have them because of my husband's health issues. Yours is the best I can do.
About: While my experience is mostly with seniors, I love and have experience with all age ranges. I've also cared for dogs that have had some medical issues and am super attentive to all my fur babies. I currently work full-time, but my hours are extremely flexible. I am in office Thurs-Sun, but my work day can end anywhere between 8am & 3pm. If I have pets in my home, I do provide a bed, feeding bowls, snacks, toys, and a lot of affection. I have a private park across the street as well as a fenced in backyard, depending on what the needs are. I am also located near Bushnell Park in case some extra running around is needed. I am good at giving medicine, if need be.
“Thank you so much for being patient w our Lily, Heather! We will definitely book again. You went above and beyond with communication and we couldn’t have asked for a better visit!”
“Tara and her cat-whisperer of a daughter did a wonderful job checking on our cat this weekend. She checked in exactly when we needed her to, and kept us updated the entire time we were away. We’re so grateful to her for making our weekend away that much more enjoyable because we had peace of mind our cat was cared for. Highly recommend Tara for your pet-sitting needs.”
“Molly is an excellent caretaker, who has provider me with multiple services while having company in from out of town or when I am traveling myself. I definitely recommend for house-sitting or drop-in visits for cats or dogs”
About: I’ve had dogs of my own my whole life and taken care of neighbors pets as well. I’ve done drop in visits and walks for neighbors dogs and cats while they were away. I currently have a dog of my own named Leo he’s a super sweet boxer lab mix who’s great with all animals and people. This summer I am free a lot and can make my schedule work around any drop ins and walks. I just need a day or two notice so I can plan around everything but I look forward to working with your pets. I love animals especially dogs. I’ve always been very kind to animals making sure they feel safe with me and know I want to care for them. I like to make sure dogs understand me and that can create some trust and build a good relationship.
About: I am a former United States Marine, retired law enforcement officer, firefighter, and paramedic with decades of experience protecting and caring for others under pressure. Throughout my career, trust, reliability, situational awareness, and compassion were essential parts of the mission, and I carry those same values into pet care today. Whether your pet needs daily walks, drop-in visits, companionship while you’re away, medication support, or attentive overnight care, you can feel confident knowing they are in calm, capable hands. I understand how important it is to trust someone entering your home and caring for members of your family, and I take that responsibility seriously. I’m comfortable with dogs of all sizes and temperaments, as well as cats and senior pets. My background has taught me patience, consistency, and how to stay calm in unexpected situations — useful skills whether handling an energetic shepherd, a stubborn bulldog, or a cat that operates like a tiny furry insurgent. I provide attention, cuddles and playtime for your fur babies- Pet care fits naturally into my daily routine. As a retired Marine and first responder, I'm accustomed to maintaining a structured schedule and being dependable. I have the flexibility to provide walks, drop-in visits, feeding, companionship, and attentive care throughout the day. I enjoy staying active, and spending time with animals is something I genuinely look forward to. When caring for pets in their own home, I do my best to maintain their normal routine to reduce stress and keep them comfortable. This includes feeding, fresh water, walks, playtime, litter box or yard cleanup, medication administration if needed, and plenty of attention and companionship. I also keep owners updated with messages and photos so they know their pets are doing well. If pets stay in my home, they will be treated like family in a safe, clean, and supervised environment. I'll follow their feeding schedule, exercise needs, and any special instructions provided by the owner. My goal is to ensure every pet feels comfortable, secure, and cared for whether they're staying with me or I'm caring for them in their own home.
The median cost per visit for dog sitting in Windsor is $22
Dog parents share their Rover experiences - Windsor
I had an excellent experience with Jalah and couldn’t be happier with the care they provided. From the very beginning, she was punctual and arrived exactly at the scheduled time, which immediately gave me confidence and peace of mind. Jalah followed all of my instructions carefully and paid close attention to the details of my pet’s routine, which I truly appreciated. It’s clear she takes her responsibility seriously and genuinely care about the animals she look after. What stood out the most was their communication.Jalah kept me consistently updated, especially during my pet’s transition to being with someone new in my home. Those updates made a huge difference and reassured me that everything was going smoothly. Overall, I highly recommend Jalah to anyone looking for someone reliable, attentive, and communicative. I would absolutely trust her again in the future!
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 near you
Select a filter and find qualifying Windsor sitters!Sitters in Windsor average 5 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 $31.08 per visit (as of July 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 July 2026, there are 2,197 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:
- 96% of sitters can help with special care needs
- 96% 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.
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.
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