Pet Sitting & Drop Ins In Windsor
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Windsor pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Nick’s care and communication have been absolutely phenomenal, and I truly appreciated it. I could tell Sebastian felt well loved and cared for through the pictures that he sent during my time away! This was my first time using Rover, and I'm sold. I'll definitely keep Nick in mind as I travel frequently, and we've had some family shifts so care is not always as readily available.”

“Danyelle is AMAZING!!! Took such great care of my boys over a holiday. Gave me daily updates and even put up with some of their eating "quirks", which isn't always easy. But she was super patient with them and gave them all the love they needed while I was gone. I was so super happy and relaxed to know they were in such great and caring hands. Heck, even just the trek to my trash can for litter box cleaning was an extra effort in and it's self. Can't recommend Danyelle enough!”

About: I’ve taken care of dogs my whole life of all sizes. I grew up with a great pyranees/ border collie and have a dog of my own who is a dachshund. I dog sat for my neighbor, friends, and relatives frequently. I also have experience in sitting for cats as well. I can also help your dog learn new tricks! I taught my dog how to sit, stay, lay down, paw, roll over, follow, and wait all within 6 months. I am currently a part-time employee and have a dog of my own, so I have plenty of time and experience in pet care to give your furbaby the care they deserve! I’m flexible to what they need. Whatever needs you have for your furbaby I can meet! My dog is very particular, so I am patient, willing and understanding to what your pet needs.
“Alyssa was great with my cat, who experiences separation anxiety. She did a wonderful job and sent me pics of my kitty getting skritches. I appreciate her care.”

About: Hi there! I'm Mitchell, an experienced and passionate dog lover excited to take care of your furry friend. Whether your dog enjoys playtime, cuddles, or quiet walks, I provide personalized care to make sure they feel safe, happy, and loved while you're away. I offer a flexible and stress-free experience for both you and your dog, with plenty of attention, exercise, and fun! Your pup’s comfort and happiness are my top priority. Looking forward to meeting your furry companion and making them feel at home!" I am excited an eager to help out taking care of your furry friends and with 18 years of having pets and three years of experience watching dogs for friends I am willing and able to do what it takes to give your dog a quality experience and help out with whatever is needed. I am a teacher in Chesterfield County so I can be available all day on weekends, Saturday and Sunday, and after 4 PM on week days. I have two dogs, one is a beagle/dachshund mix that is 3 years old and a 10 month smaller sized lab/hound mix that are both under 30 pounds and live in a two floor condo with no yard. I am able to walk dogs and do pop in visits to check on your dogs.
“Holland did a wonderful job of looking after my cat, Lucy. She was always on time, took plenty of pictures/videos, and was even able to give her eye drops. I knew that Lucy was in good hands, and appreciated her thoughtfulness. Will definitely rebook again!”

“Alexander was awesome! My silly, hyper pup warmed up to him well and he made sure my big oy was taken care of without any deviations from our routine. I will be planning on booking Alexander soon!”

About: Hi! I’m Cheyenne, a lifelong animal lover with hands-on professional experience caring for dogs of all sizes, breeds, and temperaments. I previously worked at a kennel-free dog boarding facility, where I helped care for multiple dogs at once in a safe, supervised environment. I’ve also worked as a full-time dog walker and pet sitter, providing daily walks, drop-in visits, feeding, medication administration, and lots of attention and playtime. Animals have always been part of my life—I’ve grown up with dogs and cats and currently care for my own pets as well. Because of my background in both professional animal care and customer service, I understand how important communication and trust are when someone else is caring for your pet. What you can expect when your pet is with me: • Reliable, on-time care • Regular photo and text updates • Safe handling for dogs with different temperaments • Experience with multi-dog households • Lots of attention, enrichment, and play Whether your dog needs a walk while you’re at work, drop-in visits while you’re away, or extra love and attention, I treat every pet like they’re my own. I’d love to meet you and your furry family member! I work a hybrid office jobs with very flexible hours. When I do go into the office, my office is dog friendly so I can bring a furry friend along if they enjoy the socialization! I care for pets in their own home so they can stay comfortable in a familiar environment and maintain their normal routine. For drop-in visits and house sitting, I follow the owner’s instructions closely, including feeding schedules, walks, medications if needed, playtime, and any specific routines your pet is used to. During visits, I make sure pets get the attention, exercise, and enrichment they need, whether that’s a long walk, playtime, or just companionship. I also make sure basics like fresh water, clean feeding areas, and litter boxes are taken care of. For dog walks, I focus on safe handling, appropriate exercise for your dog’s energy level, and making sure they return home happy and settled. I always send updates and photos so you know how your pet is doing while you’re away. My goal is to make sure your pet feels safe, cared for, and loved while keeping you informed and at ease.
“Jeff provided multiple days of feeding, cuddle time, walks and loving attention for our dog. The photos he sent helped us feel at ease knowing our boy was safe and happy. We appreciated his responsibility and updates!”

“Kacey was so great with Rosie! She made sure she had everything she needed and took lots of photos for us. Definitely recommend her for all your pets!”

“Elijah was great! Took wonderful care of my cat. Ran out her energy with every visit, let her take time to acclimate, and even went out on the catio with her. I can tell he’s a loving cat parent and passes that care on to his rover animals too!”

About: I offer daycare, overnight stays, walks and check ins! I’ll make sure your pet gets the love and attention they deserve. Frequent trips to the dog park and lots of long walks. As a long time pet owner I know how important it is to care for your pet properly and be able to trust they are in good hands. I have experience caring for old dogs as well as sick dogs that require lots of attention and medication. I am experienced in caring for puppies. Will provide hourly check ins when requested including photos. Dogs allowed on furniture. Will never leave them alone. Available on short notice. Hourly Over 10 years experience. Rest assured your pet will be in very good hands staying with me.
“Deanna was great! I was away longer than usual but felt confident all was well because of Deanna’s detailed updates. Everything was perfect when I came back. I would definitely use her again.”

“Maggie is so kind and wonderful with my two cats. She’s so thoughtful and detail oriented and I really appreciated her help while we were away. Maggie is a great rover!”

About: I have two dogs of my own one of which I trained to be my personal service dog. My second dog we originally were fostering and we adopted her because she fit into our family perfectly and became our other pups best friend. I actively foster puppies and kittens. I’ve done crate training and all the potty scaries with puppies. I’m extremely patient with them and try to meet each dog where they are at. I have experience giving medications to pets as one of my cats has to have daily oral medication. I love my pets and would treat yours as if they were my own 🖤 I have a very flexible schedule and I’m on the road and I have free time during the day and evenings where I am able to fit pet care-sitting into my schedule. I’m a very attentive pet parent myself and don’t typically leave my own dog unattended outside in the yard and I try to be very interactive and engage so they can play. I have 3 cats and enjoy playing with them and spending time with them so they feel cared for.

“Peyton fed our cat every night for four nights while we were away on vacation. Our cat is typically very shy and will hide when there are strangers around, but she trusted Peyton! We were sent photos of her every night with updates on how she was doing. I will definitely be booking her services again in the future!”

Windsor pet parents share their Rover experiences
Abby is a top-tier petsitter! She watched Coconut while I was away, and from the moment I left, I had complete peace of mind. She was incredibly conscientious and thorough — you can tell she genuinely cares about the animals in her care. Her consistent and detailed communication with each visit eased my mind. Without fail, she checked in twice a day with photos and detailed recaps of each visit. Seeing Coconut happy and well cared for made my time away so much more enjoyable. She went above and beyond in every way. I will absolutely be hiring Abby again and would recommend her without hesitation to anyone looking for a trustworthy, attentive, and loving petsitter. Coconut was happy and lucky to have her! 🐱

Heather was great! She was communicative, responsive, and prompt when coordinating care instructions and when reaching out in response. She followed instructions and provided consistent and helpful updates. I loved getting updates and photos throughout the day. It helped give me peace of mind while being away for 12 hours. I absolutely recommend her, and look forward to a repeat booking in the future.

We asked Grace to check in on our crazy orange cat a few times while we were out of town pretty last-minute, and she exceeded all expectations! She sent lots of pictures and gave great summaries each time she visited. Our cat hates to be alone for too long, and it was such a relief to know that Grace was giving her some much-needed love and attention! We'd definitely use Grace's services again in the future.
Per usual, Kelly's the absolute best at handling our cantankerous old man cat. I'd even go as far as saying she's growing on him, which no one has achieved before in his 15 years on this planet. Either way, we love Kelly even if Mowgli doesn't (because he hates everything).

Absolutely amazing! My dog is not always good with strangers but she loved them immediately. They were so great with her. They responded to messages quickly and listened to any pet requests. It was a 20/10 experience. I’d 100% recommend them to anyone who needs their pet watched or walked. They’re amazing people!

Popular requests near you
Select a filter and find qualifying Windsor sitters!How Rover works

1. Search
Read verified reviews by pet parents like you and choose a 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 pets while you’re away
3. Book & Pay
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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 pet 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.
Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Windsor.
Rover makes it easy to find Windsor pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.


















