Pet Sitting & Drop Ins In Winsor Hills
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 Winsor Hills pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Sophie was amazing!! I have an 80lb lab that is pretty high energy with some medical needs. I booked Sophie for drop in visits for 4 days. Sophie was incredibly thorough in her preparation, attention to detail, and communication. She took my dog to the park everyday, sent multiple pictures, and was very intentional about making sure my dog did not get over-heated outside with the current heat wave. If you're looking for someone to treat your pup like they're a VIP at the Four Seasons, book Sophie!”
About: I’ve been caring for my dogs for about 9 years now, and they truly are my babies!! I currently have a Siberian Husky and a German Shepherd, and we recently added a Golden Retriever puppy to the family!! So my puppy skills are definitely fresh right now 😊 I’m very used to high energy dogs, lots of playtime, long walks, mental enrichment, cuddle sessions, and making sure every pup feels safe, happy, and loved. Whether your dog is super playful, shy, or just wants extra TLC, I’ll always treat them like one of my own. I recently graduated from UB with my bachelor's degree and am currently in the process of applying for jobs! That means I have a very flexible schedule and plenty of free time throughout the week, so I’m typically available whenever you need care. I’m happy to work around your schedule and make things as easy as possible for both you and your pup. Your pup's safety and comfort are always my number one priority. I make sure to follow your instructions exactly, whether that’s feeding routines, walks, meds, or small things that help your dog feel at ease. I’m very mindful during walks and outdoor time, always keeping dogs securely leashed and being 100% aware of our surroundings. When I’m in your home, I respect it like it’s my own space. I keep everything clean, double check doors and gates, and make sure your pup is safe and settled before I ever step out.
About: Cashapp DoggyRoomie for any tips or gifts I have been in dog boarding for three plus years. I love caring for animals I have background in healthcare so this is an extension of what I already love to do. I also can administer insulin to your pet follow med instructions and I also do shampoos. You will be more than satisfied CASHAPP $doggyroomie For tips Greatly appreciated I have a paypal account for any tips: tips are greatly appreciated i work hard to give the best care a lot of time i will clean your pet up before the end of the boarding unless you request no special treatment. My paypal link is paypal.me/aarongene CASH APP $doggyroomie Tips greatly appreciated. Inbox me for any questions
“I can always rely on Danielle to respond quickly. She’s reliable and is a HUGE stress reliever knowing that my pup is being well taken care of. I’ve rebooked her numerous times now, and she has never disappointed”
About: I have taken care of two smaller dogs the past 3 years and have learned the hard work that comes with them. I have also volunteered at BARCS for dog days out. I am comfortable with leash trained dogs and understand feeding schedules, potty breaks, and playtime. Hello! I am currently a college student working a part-time internship and taking a summer class! I am often available on weekends and monday, wednesday, and friday nights. I know how to crate dogs if needed and have reliable transportation to an emergency vet if needed. I have grown up around cats and dogs all my life so I understand the importance of keeping your pet safe.
About: I've lived with animals all my life, from dogs to cats, lizards, snakes, tortoise's and currently chickens. So fear not! Because I love all animals 🙂↕️ This is my main source of income since the job market isn't the best, so I'm always ready to take care of some pups and kitties Whether big or small, I'll always making sure your lil guy or gal feels comfortable, is properly fed and properly walked. And if needed, I am not opposed to bringing any external needs for your pet 🫵🏾🙂↕️
About: I’ve taken care of dogs for a long time as I’ve had many dogs myself throughout my life! I love animals so much!! I work at a school full time from the end of August until the beginning of June. I will be available full time during the summer Monday-Friday all day! I have a fenced yard where your pupper will be able to walk around freely! I will also take them for walks around the neighborhood and to the park! I am willing to travel to you as well! My senior dog recently passed away and would love company!
“Susan did a great job taking care of our two dogs while we were away. We felt totally confident in her ability to care for our pets. I highly recommend Susan for your pet care needs!”
About: **PLEASE NOTE, I do not have a 6’ fence. We have a standard chain link fence. Fence jumpers are not accepted. I have had a dog since I was 19 (now 45). I love dogs and have taken in strays and nursed them to health. I have experience with small to large dogs. We have a large fenced in back and front yard for your dog to run around. We also love to cuddle. I work from home and have time to let your dog out and get some play time. We also live near a big park where we can take walks. We have a dog who is crate-trained. All dogs sleep in a crate overnight, which I provide. During the day, dogs are free to walk around both inside and outside. All you need to provide is their food and any comfort toys/blankets. I provide dog bowls
“Lindsay was absolutely amazing! She was on time, took excellent care of the girls and they absolutely loved her, and extremely communicative. We will definitely be using Lindsay again to take care of our pups! Lindsay you are the best, thank you!”
About: Experienced pet sitter caring for dogs and cats, including my grand kitties at home, providing feeding, playtime, litter care, and a calm, loving, consistent environment daily Pet sitting fits naturally into my routine, with scheduled walks, feeding, playtime, and check-ins, ensuring pets receive consistent care, attention, and comfort every day I create a safe, calm space by following routines, monitoring behavior, securing surroundings, using gentle handling, and building trust through patience, consistency, and positive interactions daily
“Shania did a really wonderful job for our cats and was really flexible and understanding of our complicated routine. She was super communicative during the visits and had to adjust on the fly for us, and she took it all completely in stride. Highly recommend her! Thank you so much again!!!”
“I feel like I left a review already but I don't see it so maybe I'm crazy. Anyway I have Samantha booked weekly to take my dog out. She is reliable and quick to respond, and very flexible, and great with my weird finicky dog.”
“My first time using Jules and DEFINITELY NOT my last. Jules was responsive and interactive with both of my dogs. She played with Roman and rubbed Coco like the princess she is. We will be booking again.”
“I really appreciated Emily taking on Benji at the last minute. She was incredibly responsive from the start and worked to ensure she and Benji could get a long for a long weekend before accepting the job. Emily checked in with me constantly and was very flexible when we decided Benji required more of her time than we'd initially planned for. When I arrived home, I could see that Benji had been given all the love and attention i would have provided him. I am very thankful to have found Emily and plan to use her on a regular basis.?”
“Bito took great care of our cats over a long weekend and sent lots of updates and photos during each visit, which we really appreciated. They spent extra time with our cats and were very communicative throughout the stay. We also came home to a very tidy house, which was thoughtful of them. Our cats seemed relaxed and well cared for when we returned.”
“I am very pleased with the service received for Kash. He was well taken care of and notifications and pictures of him on a daily were appreciated. I will definitely be booking Shakiyla again for any pet services needed in the future. Thank you 😊”
About: Hello!! My name is Sabrina and I’m currently a 2nd year graduate student at Hopkins. I’ve always been a HUGE animal lover and begged my family to adopt a pet my entire life. Now, I’ve had my family dog for 7.5 years (she’s 8.5 years now), and I am responsible taking her out every morning to do her daily poops, feed her, and play with her when I go back home in California. My friend would sometimes leave her pet at my place when she goes on vacation so I’m comfortable taking care of multiple animals at a time. Many of my friends also own cats and I always enjoy going to their places and playing with the softest animals to ever exist. I’m currently at JHU doing research about effects of microplastics on embryonic development. Since it’s mostly just research, my day is usually flexible and varies. I’m usually free on the weekends other than some Saturday mornings because I’ll be volunteering at community gardens 🐛. I can walk, feed, and play with the pets at home (and will most definitely be sending a lot of photos). I will make sure to let them have fun but also follow all the instructions given as their safety is the number one priority.
Over 2 pet parents in Winsor Hills have booked pet sitting
Winsor Hills pet parents share their Rover experiences
Sophie is amazing! We totally forgot to book someone for our sweet Asher, Sophie was super responsive, and was able to help in a pinch, because of our mix up. She’s always great with Asher, provides plenty of photos and he loves hanging out with her! 100% recommended!
We had a great experience with Reniko as our cat sitter! He took excellent care of our three cats while we were away and gave us peace of mind throughout the visit. Communication was timely and appropriate, with regular updates and photos that let us know everyone was doing well. Our cats seemed happy, comfortable, and well cared for when we returned home. He even got our shy one to say hello (an impressive feat)! We would happily book with him again and highly recommend to anyone looking for a reliable and attentive pet sitter.
I am a return customer. I made a mistake and missed the window to review on her previous visit, so I had to make sure to tell you guys how Jules is awesome. My dogs love her. Jules followed the instructions on feeding them perfectly so it’s like I never left. It’s so peaceful knowing my dogs are in good reliable care. I tell my friends to Book Jules.
Erika was wonderful with my two kitties! They were going through a finicky stage so I had to transition them to a raw diet which was a bit detailed. Erika followed everything to the letter! I love that she sent me daily photos. It was very much appreciated! Thank you Erika for giving the love and care ❤️
Lindsay was perfect! Communication was easy and timely, we met for a walk around our neighborhood prior to her watching our pup. She sent pictures during her visits with Buster and made sure he got all the pets and love! Look forward to booking with her again!
Anna is for real, the best! Every time we need to leave our boys at home we ask her to watch them because we love her so much! She’s always on time, sends lots of pictures, and takes care of our furry guys like they were her own. We would pick Anna over any other pet sitter or kennel every time.
Susan is our go to. She’s basically our pets’ god mother 🤣. Not only is she a phenomenal pet sitter with cute pics and updates.. But her knowledge of animal behavior is impeccable. 100/10 recommend her to pet sit as well as training sessions. She’s been with us since we first brought our puppy home and has made such a positive impact on her behavior. I always tell my friends/family about her!❤️
Shakiyla was an absolutely fantastic sitter! She is so knowledgeable about how to care for a big, very loving but also high energy dog like my Alba, and I felt very comfortable knowing my baby was in her care while i was so far away. She is professional, kind, responsive, and an excellent trainer as well, and I will absolutely be requesting her services in the future. Highly recommend, especially if you have a bully breed dog!
Popular requests near you
Select a filter and find qualifying Winsor Hills sitters!How Rover works
1. Search
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3. Book & Pay
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The median cost per night for pet sitting in Winsor Hills is $20
Why Choose Rover?
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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 Winsor Hills average 6 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 Winsor 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 7,526 pet sitters in Winsor 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, 87% of Winsor Hills pet sitters respond in under an hour.
Pet sitters in Winsor Hills have an average of 15 years of experience. Pet sitters with repeat customers have an average of 6 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 Winsor Hills.
Rover makes it easy to find Winsor 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 7,526 pet sitters in Winsor Hills on Rover, so you’re sure to find the perfect match for your pet! In Winsor Hills, 95% of pet sitters offer daily exercise, 98% offer medication administration, and 93% 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.
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