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

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Windsor Hills pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Renada was absolutely amazing!!! This is my first time using Rover and I was a little hesitant. Renada communicated well with me and that eased my mind. Both of my animals of course were excited to see me, however they were content when I arrived home. I enjoyed all the pics and videos of my babies! I wish I could give 1000 stars! I will definitely use Renada in the future!”

“Jeremy is amazing! The BEST with communication and chipper demeanor. He loved my dogs, and vice versa! I will be bringing him on to walk my baby girls exclusively. Cheers, Jeremy!”

“Magda has always been so sweet with our pups and sends pictures and short summaries after her visits. Her genuine love for them is easy to see and we have immense gratitude for her care. Thank you so much, Magda and thank you for the very thoughtful gift memorializing our dear Normie.”

“Linda did a wonderful job taking care of our little pups. We always felt they were safe, comfortable, and enjoying every visit under her care. Would highly recommend!!”

“Cheuk was reliable and timely, sent me info and pics of Tinkerbell everyday. Tinkbell seemed pretty calm and content which is great since she’s getting grumpy as she ages. Thank you for taking care of her Cheuk!”

“Clem always takes such amazing care of our cat, Bigby! Clem is sends wonderful updates and pictures with every visit, I always know he’s in good hands and being well cared for.”

“Thank you so much Trina! We really appreciate your willingness to bring her home from daycare for us, safe and sound! Super communicative, punctual, and helpful in a pinch. We’re so grateful to Trina!”

“Kyle is communicative and personable, she did a great job of taking care of my boys! I appreciated the photos she sent during their check-ins, which were prompt and timely.”


“Marisa was amazing! My animals loved having her come check on them, and I felt really comfortable knowing they were in good hands. She gave me detailed updates after every visit and kept me informed on how they were doing. I’m so glad I chose her to take care of my pets and would definitely recommend her to anyone looking for someone reliable and caring. :)”


“This is the second review I have done for Melissa, but y’all you can stop your search here. She. Is. THE. Best. Spends extra time with your pets, sends tons of cute pics, goes above and beyond pet care, and an excellent communicator. Book her! 💯”


“Alice was a lifesaver and was able to dog sit for us last minute. She was attentive to all the details for Stella’s care needs and was respectful to our home. Very responsible and professional! Thank you Alice!”

About: I have 10 years of experience with rowdy pups, with three of my own! I’m happy to meet your furry friends, and take them off your hands so you can relax! I work from home, and have a very open and flexible schedule! I am available for drop ins, walks, play and boarding! My goal is to help you as best as possible! I have a large fenced yard, and 3 furry friends to play. If your pup prefers privacy, I have plenty of space and rooms they can hide in, and keep them separate!
About: Hi there! I'm Stacy, and I’ve been caring for dogs for over 20 years. As someone who has always had a deep connection with dogs, I understand how important they are to your family. My goal is to provide a calm, loving environment where your dog can feel right at home while you're away. I approach pet care with patience and empathy, always making sure your furry friend feels comfortable and loved. Whether it's playtime, walks, or just cuddling up on the couch, I aim to give your dog the same attention and affection they get from you. I’m especially passionate about getting outdoors with dogs—they help me get out of my head and enjoy the simple joys of life. Your dog’s safety and happiness are my top priority, and I’ll treat them with the same care and respect I give my own pets. I can’t wait to meet your dog and make sure they feel safe and loved while you’re away! Pet care is truly a part of my daily rhythm. My days start with a morning walk—either with my own dog or one I’m caring for—which sets the tone for a calm, active day. I always ensure that I have dedicated time to interact, play, and give love to the dogs in my care. Throughout the day, I’m flexible, keeping a routine that meets each dog’s individual needs, whether that’s regular potty breaks or quiet downtime. I incorporate outdoor walks into my schedule because I believe dogs need that fresh air and exercise to stay happy and healthy, and I love to get outside myself. My calm approach helps create a safe, stress-free environment for the dogs I care for, ensuring they feel secure and relaxed. Even in my downtime, I keep the dogs in mind—whether it’s making sure their toys are accessible, preparing meals, or simply giving them the attention they need. It’s a balance of activity and rest that ensures they feel content all day long. I have a fenced backyard, and it's perfect for hanging out or playing with your dog. Lots of different areas to smell and explore (blackberries, roses, vegetable garden).
“Savanah was super helpful and caring with our pets! We needed some last-minute holiday help and Savanah made us super comfortable leaving our pets in someone else’s hands. Highly recommend!”

“Samantha did a wonderful job taking care of my cat Benny. He is very picky and can be grumpy but she sent great photos and was always on time and I didn’t have to worry while we were away.”

“ChunYu was an AMAZING sitter for my two cats! She was extremely responsive and descriptive in her recaps of her visits. She also very clearly gave lots of attention, energy, and loving to them, would 500% book again.”

“Olivia is prompt in their responses and gives valuable info in their visit reports. i've got a neurotic lil weirdo dog who seems to really like them. I trust Olivia and feel comfortable leaving my dog in their care”

“Shane did great with the dogs! He let them out and followed all our instructions. We even had a last minute change up with instructions bc one of our pups got a boo-boo requiring him to wear a cone and Shane was super accommodating and responsive. Would have him come hang with our pups again!”

“Michelle was absolutely amazing! She was always on time and kept me updated on my cat the entire weekend! My girl was very happy and content when I got home, so I know she was well taken care of! We will definitely be using her in the future!”

“Kendall did a drop-in with Mara to get to know her prior to a weeklong trip. Mara took to her immediately, all instructions were followed, and she sent great photos. Thank you, Kendall!”

Over 4,190 pet parents in Windsor Hills have booked pet sitting
Windsor Hills pet parents share their Rover experiences
Sophie did a wonderful job taking care of my cat while I was away. She was very responsible, responded quickly to all my questions, and shared daily photos and updates, which gave me great peace of mind. It was clear that she genuinely cared for my cat and made sure everything was well taken care of. I would definitely ask for her help again in the future and highly recommend her to anyone looking for a reliable pet sitter.

Debra is my go to sitter and an absolute gem ❤️. Her daily updates often make me laugh and feel like I'm right there with my babies. My cats adore her and it's clear she adores them in return. I can go out of town and trust with full confidence that the most important things in my life are being taken care of in the way I would. I love her, I will continue to entrust my kitties with her, and I would 200% recomm

Madison did an amazing job taking care of our two cats while we were away. It’s always nerve-wracking hiring someone new to watch after your pets but her professionalism and reliability gave me peace of mind. She is quick to respond and completed each visit with thorough notes and pictures of her playing with them. She went above and beyond to make sure they received the best care possible, checking in with us about anything she noticed and making sure all their needs were met. We will definitely be hiring Madison again for future trips because we feel comfortable knowing our boys are in such capable and caring hands. I highly recommend her for your next booking!
We love working with Jenna! She's watched our dog twice for us now, and she is great about helping us settle on a schedule, being consistent, and communicating with us about how things are going. Our dog is sweet, but he is reactive towards other dogs, and she's handled his behavior extremely well for us. Youll be glad you hired her ☺️

Popular requests near you
Select a filter and find qualifying Windsor Hills 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
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 pet sitting in Windsor Hills is $20
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.
Sitters in Windsor Hills average 7 repeat pet sitting clients
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Windsor Hills on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Jun 2026, there are 7,273 pet sitters in Windsor Hills. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 89% of Windsor Hills pet sitters respond in under an hour.
Pet sitters in Windsor Hills have an average of 15 years of experience. Pet sitters with repeat customers have an average of 7 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Windsor Hills.
Rover makes it easy to find Windsor Hills 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
There are 7,273 pet sitters in Windsor Hills on Rover, so you’re sure to find the perfect match for your pet! In Windsor Hills, 96% of pet sitters offer daily exercise, 96% offer medication administration, and 91% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
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.
















