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Top rated Windsor house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Jessica had pup-sitted for my very anxious dog and she has done great with him! His anxiety is way down and he’s relaxed enough to even play around! I’m grateful we found her and that my pup loves her.”

About: I’ve had over 10 years of hands on experience caring for dogs and understand the responsibility and attention they need to stay happy and healthy. I currently have two Labrador Retrievers who are very energetic, so I’m used to managing high-energy dogs and keeping them active and engaged. I’ve also spent time helping out at local dog shelters, assisting with feeding, cleaning, and giving dogs attention and care. This experience has helped me become patient, attentive, and comfortable with dogs of all temperaments. I work weekdays in the morning to mid day usually, and my weekend availability can vary. However, I manage my schedule carefully and plan ahead, allowing me to stay flexible and reliably accommodate pet care needs when needed. Safety and trust are really important to me when caring for pets. Whether I’m in my home or a client’s home, I make sure the space is clean, safe, and free from anything that could be harmful. I stick closely to each pet’s routine, including feeding, walks, and any specific instructions. I pay attention to their behavior to make sure they feel comfortable and not stressed. I also keep a calm, supervised environment and treat every home with respect, so both pets and owners feel at ease.
About: I have been around cats and dogs all my life. I just love all animals. Dog walking is great for their physical and mental health/improves their joints, and all around good therapy for me and your pet. Play time is also important. I will treat your furry family member with the utmost care & diligence. I am responsible, attentive, & detail oriented and will provide quality services. Currently available during the day. Just about anyday with a little notice. Can set up regular scheduled walk times. Or if you are in a bind, and need, on spur of notice. I am willing to walk from your home, or to a near by park. Giving attention and time. I typically like to know if they have a specific diet, medications, preferences, etc.
“Cheyene took great care of our dogs while we were away. She spent alot of time with them and took them for walks. We left instructions for her, and she followed them diligently. She took great care to provide for them while also caring for our property. Everything was in perfect order on our return! Cheyene is a great communicator - quick turnaround time, asked great questions, sought clarifications as needed. This was our very first experience with a dog sitter, and we are beyond pleased. We will definitely utilize Cheyene services in the future if she is available! Thank you!”

“Billie is definitely one of my favorite rover sitters to date! She was highly responsive during the booking/meet and greet process and very communicative throughout the duration of the stay. We received multiple updates a day with multiple photos which definitely put us at ease since one of our dogs can sometimes shut down a little while we are away. Billie did great with both of our dogs and even the one who typically hides while we are gone was a big fan - he was out and social most of the stay. Billie also left our house immaculate. Cannot give her enough praise, will definitely look to book more of our sittings with Billie in the future.”

About: I’ve cared for cats my entire life and have experience with a wide range of personalities, from social and affectionate to shy or recently rescued. I’ve provided pet sitting for family and friends, including both cats and dogs. I also have hands on experience helping stray and rescue cats adjust to indoor environments. In addition, I’m comfortable handling small animals and have experience owning and caring for ferrets. I prioritize patience, consistency, and understanding each pet’s individual needs to make sure they feel safe and comfortable while in my care. I currently just graduated high school at York County School of Technology while enrolled in the Licensed Cosmetology program! I obtained my cosmetology license in December of 2025. I’m currently waiting to begin my journey in the esthetics side of the cosmetology industry! I have a very flexible schedule on the weekends, as well as mid afternoon and nights. I personally prioritize creating a safe, calm, and stress free environment for every pet in my care. I take the time to understand each pet’s routine, behavior, and any specific needs so I can keep their environment consistent and comfortable. I’m attentive to details such as securing doors, safe feeding practices, and monitoring behavior for any signs of stress or illness. I’m also respectful of client homes and follow all instructions carefully to ensure both pets and property are well cared for. For more anxious or shy animals, I focus on patience and gentleness to build trust at their pace. I’m happy to provide regular updates, photos, and communication so you feel confident and informed while you’re away.
“Caleb was wonderful! He took great care of our dog Sully. He even stopped by the day before to get to know him. Caleb was incredibly attentive, caring, and responsible. Sully was so happy that he did zoomies! I highly recommend him to anyone looking for reliable and loving care for their furry friends. We are looking forward to hiring Caleb again.”

“Jen helped us out last minute and watched our dog who has separation anxiety. I had never left my dog with a sitter before but I could tell before I left that my dog was comfortable with her. It’s very obvious Jen is an animal lover. She did a fantastic job with my dog and I’d recommend her to anyone.”

“This was our first time using Rover.com for our two rambunctious young pups. We were nervous about leaving Gracie and Tuck, but Lauren and her husband Doug did an OUTSTANDING job of watching them in our home. They sent lots of pictures and messages and it really helped to reassure us they were safe and felt comfortable in their new situation. We had a great time on vacation, but seeing the pics of the pups and learning about their adventures each day was our biggest highlight. We are so appreciative for Lauren and Doug’s patience, kindness and care of our furry kids and we highly recommend them.”

About: I have a deep love for animals and years of hands-on experience caring for dogs with a wide range of needs, especially senior dogs. I understand that older pets often require extra patience, attention, and gentle care, and I’m committed to making them feel safe, comfortable, and loved while their owners are away. I’m experienced in administering both oral and topical medications and am comfortable following detailed care routines to ensure pets stay healthy and happy. Whether it’s managing medication schedules, providing calm companionship, or adapting to mobility or dietary needs, I take pride in giving each pet the individualized care they deserve. Above all, I treat every animal as if they were my own. Building trust with pets and their owners is incredibly important to me, and I strive to create a stress-free, nurturing environment where animals feel secure, cared for, and genuinely loved. For boarding, your pet will have a structured and caring environment throughout the day. I work full time from 7:30 AM to 5:00 PM, and my boyfriend works from 5:30 AM to 1:30 PM, which means there are only a few hours in the late afternoon when pets would be home alone. In the mornings, pets will get potty breaks, fresh water, and breakfast before the day begins. My boyfriend is home by early afternoon and is able to give them attention, potty breaks, and companionship during that time. When I return home in the evening, pets receive plenty of attention, playtime, walks (for dogs), feeding if needed, and a calm, relaxing evening routine. A typical day in our home is calm, structured, and full of attention for the animals. We have a fully fenced yard where dogs can safely enjoy outdoor time, sniff around, and stretch their legs throughout the day. Mornings usually start with potty breaks in the yard for the dogs, followed by breakfast and fresh water for everyone. After that, there’s some relaxed time while everyone settles into the day. Our two resident dogs are friendly and used to having other animals around, and our two cats are part of the household rhythm as well. During the afternoon, the dogs get more time outside in the fenced yard for potty breaks and play. There’s also indoor time for rest, toys, and companionship. We make sure pets have comfortable spaces where they can relax and feel at home. In the evening when everyone is home, the animals get plenty of attention, playtime, and interaction. Dogs can enjoy additional outdoor time in the yard, and all pets receive dinner if it’s part of their routine. The night usually winds down with a calm, cozy environment where the animals can relax and settle in comfortably. Throughout the day, I pay close attention to each pet’s personality and needs—whether they want to play, explore the yard, or simply relax nearby. My goal is to create a safe, loving environment where every pet feels like part of the family while they’re staying with us.
About: From pet-sitting duties and caring for my own animals, I have extensive experience caring for a variety of animals, including feeding, grooming, and providing companionship. I’ve also administered medication to dogs of all ages and sizes, ensuring proper dosage and handling for each. I'm a proud graduate of Bloomsburg University with a bachelor's degree in early childhood education. I also enjoy working part-time in the restaurant industry. My schedule is quite flexible as long as I have some prior notice! I'm happy to work with clients to find times that suit us both well. I'll make sure to follow all of your instructions carefully to keep your little buddy happy! Do you have any specific wishes for them? Just let me know! I welcome them on my bed and couch unless you'd prefer otherwise. I always keep the water bowl full and ensure pets are happy and healthy. If you'd like, I can even give them a bath—just bring their shampoo if they have sensitive skin! If you choose me, I promise to go above and beyond to take great care of your furry friend!
“Treanne sat overnight for our 15 year old dog, Fox between June 30th - July 5th. I was so happy with our experience- she was so attentive to our guy especially with his age and neighbors shooting fireworks over the 4th. She sent daily pictures and updates with him. I had a peace of mind while being away. If we go away again, I would not hesitate to book Treanne again.”

“Ashton was great with our two dogs! They warmed up to him almost immediately and he was very thoughtful in their care. He was very responsive and prudent with being on time and keeping them on a schedule. Also left the house exactly how he found it which was a huge relief being able to come home to a clean house! Would absolutely recommend!”

“We cannot recommend Ronny highly enough! When another sitter backed out at the last minute, we reached out to Ronny on short notice. He responded promptly and was more than willing to come by for a meet and greet, which immediately put us at ease. From the moment he walked in the door, our cats were comfortable with him which is not always the case. Ronny took his time answering all of our questions and asked thoughtful questions of his own. Even though we admittedly have a very detailed list of instructions, he did an amazing job remembering all the little things and checking in regularly with messages and photos throughout his stay. It was clear that Ronny genuinely cared about making sure our cats were happy, comfortable, and well loved while we were away. He was also incredibly respectful of our home, leaving everything exactly as we left it. He even went above and beyond by offering to clear our driveway after an unexpected snowfall. If you’re looking for someone who truly goes the extra mile and treats your pets like their own, Ronny is absolutely the person to book!”

“Brittany did a fantastic job taking care of our pups! We had to book her last minute for the weekend and she took care of everything like a pro. Both of our babies took right to her right away and spent the day glued to her side. Brittany was everything you want from someone watching your pets- reliable, trustworthy, professional and caring. Would love to have her watch them again.”

About: I’ve had cats all of my life, and have dog-sat for friends, neighbors, and coworkers since becoming an adult. My own little orange kitty has many medical adventures—so I’m also very used to administering medicine to cats. I have flexibility in my work hours and can work around routine meetings - allowing for flexibility when caring for our loved ones! I know some furballs need more together time than others so also have a job where I can work virtually too! I love working under instruction—every pet is different and needs different attention and affection! I love to give cuddles and have playtime, and am very detail-oriented when taking care of pets.
Over 2 pet parents in Windsor have booked house sitting
Windsor pet parents share their Rover experiences
Cheyene took great care of our dogs while we were away. She spent alot of time with them and took them for walks. We left instructions for her, and she followed them diligently. She took great care to provide for them while also caring for our property. Everything was in perfect order on our return! Cheyene is a great communicator - quick turnaround time, asked great questions, sought clarifications as needed. This was our very first experience with a dog sitter, and we are beyond pleased. We will definitely utilize Cheyene services in the future if she is available! Thank you!

Ken had a real challenge with hanging with our Finn for 10 days. We’re very specific about his care and find it hard to trust people with him. We were beyond pleased with Ken’s care of Finn! He asked questions and kept us updated throughout our long trip. When we got home, Finn was very obviously well cared for. Not only that, but our house was clean and tidy! You would’ve never known someone was there. 10/10 would recommend Ken for your doggy care needs! Thank you again!

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Windsor is $50
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 house 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.
Sitters in Windsor average 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Windsor on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 794 house sitters in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 88% of Windsor house sitters respond in under an hour.
House sitters in Windsor have an average of 16 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Windsor.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Windsor house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.




