Dog Sitting Windsor
Book a Windsor dog sitter to watch your dog in your sitter’s home or yours.
Over 17 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: Hi I’m Hailey! Growing up my family always had both cats and dogs so I’m very comfortable taking care of pets. I have years of experience with both dog and cat sitting for both short and long term stays. I love to be active and take dogs on walks around the neighborhood and can customize my schedule to fit their needs. I work part time and have a pretty flexible schedule. I can work based around you and your pet’s needs! Available weekdays as well as weekends. I have dog sat for both large and small dogs before and have no issue with tailoring to their needs. I have years of experience pet sitting for long term stays up to a month for dogs, cats, and chickens alike!
“Caroline is an amazing cat sitter. She took care of my cat, made her feel safe, fed her and kept her area clean. She made the whole experience great. I would highly recommend her.”
“Andrea is great! She communicated throughout the entire process. She kept me informed on how everything was going. She sent pictures showing her interaction with Snuggles. Although, she wasn’t booked to care for the cat, she notified me of his mischievous behavior. I will definitely book with Andrea again. Thank you Andrea!”
“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: I’ve taken care of dogs my entire life, for neighbors, family, and my own golden retriever Penelope! I’m in nursing school in West Hartford and am looking to help you! I’m currently in Nursing school and am available to stop by basically all hours of the day. I’m happy to help before or after class! I provide reliable, loving pet care tailored to each animal’s routine, including walks, feeding, playtime, medication, and plenty of attention! Most importantly I’ll keep your pets safe and comfortable.
“Ifan did an incredible job taking care of my Bernedoodle, who is full of energy and absolutely loves meeting new people. They handled his excitement with total confidence and experience, which immediately put me at ease. He got plenty of playtime in the backyard, lots of social interaction, and even came home tired and happy which is a rare accomplishment for a dog who could play all day. It was clear that Ifan really understands energetic dogs and knows how to keep them engaged in a positive way. My dog adored them, and I could tell he felt comfortable and well cared for the entire time. I would absolutely book again and highly recommend them to anyone looking for a skilled, attentive, and genuinely caring sitter.”
“This was the first time I booked Le'Andra to do daily check-ins on my cat Gabby while I was out of town. She was great! Le'Andra always stayed in communication with me by text. And she did her best to still take care of my cat while also dealing with the storm and very cold temperatures we recently had. Le'Andra is nice and very friendly. I would definitely request her again the next time I need a cat sitter, and would also recommend her to anyone considering booking her on Rover.”
About: Even though I don't have a lot of certified training, I know how to show my love and affection to each and everyone pets just like I have in the past for my own. I am currently unemployed, and I will be starting to go back to school in the fall semester of this year, so my availability is kind of flexible during the week, except for Wednesday's Thursday and Sunday. I will treat every one's pet with love, care, respect and patience that they need and treat them as one of my own family members.
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: Hi, I am a work from home college student, I have been pet sitting for over 4 years and I have a loving toy cockapoo of my own. I have a large fenced in yard along with plenty of indoor space for cuddles, lounging, and running around. I follow pet parents routine for walk/eating allowing with optional photos/videos. I look forward to hosting your pet where dogs become family I work from home part time so I am always here with a flexible schedule to do walks, take breaks, and keep an eye on our furry friends! I have a large fenced in yard, my care depends on the pets needs, so weather they like long walks, cuddles, lounging on couch or deck, there needs will be catered to and pets will be well taken care of:)
About: I’ve taken care of my dog, AKA my brother, for 12 years from pup, to angel. I’ve never had any siblings so he was all I had. But I learned a lot about being compassionate towards animals through my short time with him. I believe I can provide the same love I gave to my little bro, to all dogs! Even though I don’t think I will get another dog, I still want that same love and joy I get with dogs! I am currently a nursing student looking for a good way to do what a love while earning some money. I have lecture on Wednesdays from 10:30am-1:30pm and clinicals from 2pm-11pm on Thursdays, other than that, my schedule is free. The house is usually never empty. I have a fenced yard built for a 100lb Weimaraner, so trust that it will hold your doggies. I always split meals 3 times a day, breakfast, lunch, dinner. Bathroom breaks happen always in the morning and before bed. More bathroom breaks can happen as needed. Dog walking usually happens in the mornings when before it gets hot. Playtime happens when requested by the doggies. Treats are available for good pups as needed.
About: I had dogs for the first 24 years of my life, and believe no time spent with animals is wasted. I've cat sit and roomed with cats in the past and now love them just as much. I've worked with various animals throughout my life, from working at a horseback riding camp, to a pet store, to an animal sanctuary. my weekends are Sunday-Monday. I work as an archivist at a museum 9-5 during the week, but I'm still happy to take evening/nighttime bookings on work days. I genuinely enjoy spending time with animals I've been a pet owner most of my life, and an animal lover for all of it. I've worked with animals across multiple jobs in my life. All animals have unique personalities, so adaptation and individualized care is very important to me. My roommates and I do not have any pets currently. We keep a clean and cozy spacious apartment near Elizabeth Park.
“Arianna was absolutely amazing with our pup Oakley. She gives the confidence to be able to handle any situation that may come up. Highly recommend, and will be using her services again!!”
“Jen was fantastic. She handled my sometimes not so well behaved cat perfectly and took some awesome pictures. Responsible and communicated well- would love to have Jen watch my cats again sometime.”
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.
The median cost per visit for dog sitting in Windsor is $22
Dog parents share their Rover experiences - Windsor
Berkley was absolutely wonderful with my dog! She was extremely communicative, followed all of my instructions perfectly. I really appreciated all of the photos she sent—they made me feel so comfortable knowing my pup was in good hands. Berkley was reliable, caring, and clearly loves what she does. I would absolutely recommend her and will definitely be booking with her 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.
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 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 $22.2 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 2,181 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
- 97% 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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