Pet Sitting & Drop Ins In Winnetka
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 Winnetka pet sitters
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Ethen was excellent with my little dog Olina. By sending pictures and reporting the daily activities made me feel comfortable the my dog is in good hands. I would definitely have Ethen to look after my furry baby.”

“Megan was great, she sent photos of Chilito every time she came to visit him. If I had any questions she was always very responsive. I would love to have her back next time I need a sitter.”

“This was our first time using Rover so we were a bit nervous about leaving our puppies and going on vacation. Brooke did a fantastic job and we will be happy to hire her again to take care of our dogs.”

“Adeline is such a gem—so sweet, caring, and passionate. She’s wonderful with my 4-year-old, AMAZING with my puppy, and my dogs cherish her as much as I do. She’s reliable, attentive, and I know I can count on her to give the best care. I’m so grateful to have found her as our weekly sitter. She’s the best!!”

“Kristen was coming to drop-in and walk/feed our 2 large dogs - she was very communicative, thorough in her reports and we got lots of pictures. Kristen was a real professional and was very attentive with our dogs needs, especially with our one high anxiety dog. We could tell both our pups took an immediate liking to her! We’re definitely going to be re-booking with Kristen again when we need a fantastic sitter for our dogs!”
“Samantha is doing such a great job taking care of my cat Tyler while I’m out of town. I love the thought and attention she puts into her reviews and photos. You can tell she gets along with pets naturally. thanks Sam!”

About: I stand out for my hands on experience caring for pets with a wide range of needs, including senior dogs who require medication morning and night, cats who need medication, and dogs with anxiety who benefit from a calm, patient approach. I’m experienced with overnight care, vet visits, walks, and maintaining consistent routines. I’m reliable, attentive, and prioritize clear communication, providing regular updates so pet owners always feel confident and at ease. I currently have a very open and flexible schedule, which allows me to dedicate plenty of time and attention to pet care. I’m available throughout the week for walks, drop-ins, and overnight care, including mornings, afternoons, and evenings, as well as weekends. I’m able to adjust to your pet’s routine and make sure they get consistent care, attention, and exercise. I provide a safe, calm, and loving environment for every pet in my care. I will always follow your pet’s routine closely. I pay close attention to behavior, comfort, and safety at all times, and I’m experienced with administering medication and caring for pets with anxiety or special needs. My goal is to make your pet feel comfortable, secure, and at home.
“I had a great experience with Anna. I was comfortable leaving my 2 dogs with her while I was traveling. She was taking good care of them, made each visit on time and kept me updated about everything.”

“Vanessa is fantastic! Very thorough with any directions and loves on my for babe like I would! Makes long days at work very stress free knowing Hazel is in good hands!”


“We have used Lexy before and will use her again to check in on our dog, Milo! She is wonderful with him and he absolutely loves her visits. Lexy puts my mind at ease knowing he is in great care while I am out of the house for the day. She sends lots of videos and pictures of her visits, which is a lovely little touch!”

“Sanaz is very reliable, communicates well, and takes great photos that always made me feel comfortable that my cat is ok. I booked last minute and she was able to stop in for every visit needed. My cat took a couple of days to come out and when he finally did he was so happy she was there. With Sanaz I can trust that when I come home that my furry best friend is ok.”

“Victoria was absolutely amazing! She took great care of our dog and kept us updated with each of her visits. She is so kind, our dog loves her! Definitely going to be using her again! She’s the best!”

About: Hello my name is Brooke! I’ve spent years caring for and training my own dog, which has given me a deep understanding of dog behavior, communication, and positive reinforcement. I’m especially comfortable with larger breeds and dogs that need a little extra patience and structure. What sets me apart is my calm, confident approach and genuine love for animals. I treat every pet like my own; making sure they feel safe, loved, and understood. Whether it’s walks, playtime, or just keeping them company, I make sure each dog gets the attention and care they deserve. I'm currently working part-time which gives me plenty of flexibility to care for pets and spend quality time with them. My schedule allows me to do walks, drop-ins, and pet sitting during most mornings, afternoons, and evenings. I always make sure pets get the attention and consistency they need while their owners are away. When caring for pets, I focus on keeping them comfortable, happy, and on their usual routine. In my home, dogs have a calm, safe space to relax, regular walks, playtime, and lots of love. I make sure they always have fresh water, a cozy spot to rest, and plenty of attention. When I’m in a client’s home, I follow their care instructions closely, from feeding schedules to favorite toys and walking routes. I always treat each home and pet with respect, keeping things clean and making sure your furry friend feels safe and cared for while you’re away.
“Julianna is awesome! So glad we found her! I travel occasionally for work is she is always my go to for house sitting Kona. Great communication and Kona loves her! I feel very comfortable when I’m gone knowing Julianna is taking great care of her. Thanks Julianna!”

About: Hi! I’m Josefina, I’m a lifelong dog lover and experienced foster for local shelters. Over the years, I’ve cared for dogs of all breeds, sizes, and personalities, from playful puppies to senior sweethearts. I also have pets of my own, so I understand how much trust it takes to leave your furry family member in someone else’s care. My goal is simple: to make your pets feel loved, safe, and happy while giving you total peace of mind. Pet care is part of my everyday life. I have dogs of my own and foster pups regularly, so caring for pets is already built into my daily routine. I schedule plenty of time for walks, play, feeding, and snuggles throughout the day. Whether it’s early morning walks, midday potty breaks, or evening playtime, I make sure pets get the attention and care they need. In my home, pets have a safe, clean, and welcoming environment with plenty of space to relax and play. I have two friendly dogs who love making new friends, so your pup will have great company. I follow your care instructions closely, feeding schedules, medications, and routines are all important to me. When caring for pets in a client’s home, I keep their routine consistent and provide lots of love, plus updates and photos for peace of mind.
“Mikayla is an absolute life saver. Not only did she give me peace of mind while I left my boys for the first time ever. She not only made sure they had everything they needed, but went above and beyond every single time. It’s hard to find people that you can trust in both your home and with your fur babies and she does both!”

Winnetka pet parents share their Rover experiences
Sanaz took wonderful care of my two cats while I was away for two weeks. She visited every day to feed and check on them, and she consistently sent photos and videos that gave me peace of mind while traveling. She was reliable, responsible, and a pleasure to work with throughout the entire experience. I came home to two happy, well-cared-for cats. I would definitely book Sanaz again and highly recommend her to anyone looking for a trustworthy pet sitter.

We are so happy we found Cecilia to take care of our two cats. It was a huge relief to be able to relax and enjoy our vacation knowing that they were in good hands. Cecilia was super responsive to messages, very reliable and consistent with time, and she even managed to get our very shy rescue cat come out to say hello! The photos she sent every day made us smile and we knew the cats were happy based on their behavior. We would highly recommend and will absolutely be booking Cecilia again next time we travel!

Shahrzad is an amazing sitter! We have used her three times now and she is always on time for feeding and playtime. She is very sweet with all my pets, 3 large dogs and a cat! Shahrzad takes her work very seriously and sends pictures and videos every day. She makes sure the animals have all that they need before she leaves after her drop in. She loves dogs and engages in fun play activities with them! Highly recommend to everyone!
Adriana is a natural with cats. We have two cats, one is outgoing and friendly, the other is shy and friendly. I didn't think she'd see the shy one for a few days, but during our meet Adriana sat down and the shy cat came running to her. Adriana visited the cats daily while we were away, took care of everything on our checklist and provided great photos along with a summary of each visit. 10/10 would recommend!
Halle provided 3x a day drop in visits over four days. She was always on time and stayed with Luka for at least the the amount of time requested. Halle did everything asked of her and bonded nicely with Luka. So much so, that I'm sure Luka was hoping that it was Halle at the door instead of us. I would gladly have Halle watch Luka again.

Athena was fantastic, not at all fazed by having three dogs at once, one of which can be a little hard to handle. A true professional who has experience. Athena is friendly with a calm manner that helps the dogs feel more at ease. I have already rebooked, highly recommended.

Popular requests near you
Select a filter and find qualifying Winnetka 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 Winnetka.
Rover makes it easy to find Winnetka 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.
















