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Top rated Winnetka house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Keeley was an amazing sitter. Sent so many pictures and updates and truly just loved on our pet with cuddles, car rides and great walks and playtime. Left the house clean and tidy and was just a pleasure to work with. Will be rebooking her soon!”
“Samantha went above and beyond for our giant Newfie. She was very communicative and sent photos and offered to stay a bit longer with him the day we were flying back home. She administered medication and made sure he ate at the right times. He’s also a big mess (slobber and shedding) and I was shocked when I walked in - it was obvious she cleaned up after him which I was not expecting. She was truly amazing :)”
“Jason did a great job watching our dogs. He sent frequent, high quality photos throughout the stay, which we very much appreciated. He gave our pups lots of outside time and dealt well with administering their meds. We’d book with Jason again and recommend him to others.”
“I was terrified about finding someone to watch my little Velcro baby. But Rebeca put me at ease. Her communication with me and love she gave my baby is beyond what I could have expected. I am so happy to have book with Rebeca and next time I am in Chicagoland I will definitely book with her again! Thank you Rebeca!!!”
“Shailyn stayed at our home for 4 nights and took great care of the house and our beloved Lucky!! Neighbors said Lucky looked very happy on his walks while we were gone. Very thankful for her giving Lucky lots of love while we were gone!”
“Emily was incredible. She didn’t just watch my dog, she cared for him like he was her own and treated my home with the same thoughtfulness and respect. From the moment they met, my dog was instantly comfortable with her. She played with him, took him on walks and runs, and gave him all the snuggles and attention he could possibly want. She sent tons of photo updates, which gave me so much peace of mind while I was away. But what really made her stand out is how considerate she was with my home. Everything was spotless when I returned, and she even stayed until I got back so he didn’t have to be alone. I walked into a sweet welcome note and fresh flowers, such a thoughtful touch and a truly warm homecoming. I cannot recommend Emily highly enough. She is attentive, trustworthy, incredibly kind, and clearly loves what she does. I’d book her again in a heartbeat!.”
“I couldn’t have asked for a better pet and house sitter. When I first met Mer, she was clearly experienced and comfortable with Walter (he can come on a little strong since he loves visitors) but she wasn’t intimidated at all. Mer took the time to understand Walters routines and quirks (he has many) which immediately made me feel comfortable about trusting her with my big 90 pound baby. While I was away, we kept in touch so I knew Walter was well cared for. The photos looked like they were having a great time! Mer treated my home and my dog with kindness and respect, as if they were her own. I would definitely recommend Mer and will be booking her again next trip.”
“Outstanding care. What more can you ask for when you leave your home and pets in someone else's care? That's what Donna delivered in spades. Donna was responsive, proactive, caring and considerate. She was in instant contact and everything was breezily coordinated prior to our trip. Once we left, Donna kept in constant communication and delivered on everything she said she would do. When I came home my pets were healthy and happy but I was stunned to discover how neatly everything had been left. 10/10, will ask for again, thank you, thank you, thank you, Donna.”
“Iwona is great with our dogs! She has house sat for us twice and taken such amazing care of both the dogs and the house. She loves on our dogs so well, they barely even notice that we are gone!”
“Michael was fantastic! We have 2 large dogs, one has pretty bad anxiety, he handled him so well! He communicated, sent pictures, and really cared about taking care of our dogs! I would recommend him to anyone. He did some training with our dogs as well which helps with getting energy out, I just really appreciate how caring he was with our dogs!”
“Tiffany was a fantastic house sitter for our 9-month-old puppy! She was responsive, professional, and made sure our dog felt comfortable and well cared for while we were away - which gave us great peace of mind. We will definitely use her again and highly recommend her!”
About: I’ve been around dogs my entire life, mostly chihuahuas and rescues, so I’m very comfortable with pups who need a little extra patience, reassurance, or understanding. My hands-on experience goes far beyond casual pet care. At Miami University, I was part of Paws for a Cause, where we helped train dogs to prepare them for working with children or future companion roles. This gave me a strong foundation in obedience training, reading body language, and supporting dogs with different temperaments. More recently, I’ve been volunteering with the Evanston Animal Shelter, working with dogs who have a wide range of behaviors and needs. There, I’ve assisted with medication administration, training sessions, enrichment, and helping nervous or high-energy dogs feel more comfortable and confident. I’m also on a path toward becoming a Physician Assistant, which adds to my calm, attentive, and health-focused approach. I’m comfortable managing routines, monitoring for changes, and making sure each dog feels safe and cared for. Overall, I bring a mix of lifelong experience, formal training exposure, shelter work, and genuine love for dogs of all personalities. Your pet will be treated with patience, structure, and plenty of affection. I work full-time as a medical scribe during the day (9–5), so evenings, weekends, and holidays are when I’m most available for pet care. During those times, I’m fully focused on your pet’s needs—whether that’s walks, playtime, feeding, or just keeping them company. My schedule outside of work is very flexible, so I can reliably fit in consistent visits or longer stays. When I’m caring for pets in a client’s home, I follow their normal routine as closely as possible—feeding schedules, walk times, crate routines, and any training cues you use. I take time to get to know your pet’s personality, comfort level, and boundaries so they feel safe and relaxed. I provide plenty of attention, enrichment, and calm companionship, and I always keep water fresh, watch for behavior changes, and send regular updates so you feel connected. If I’m hosting in my home (or doing extended stays), I make sure pets have a quiet, clean space to settle in, regular potty breaks, structured playtime, and a consistent routine. Safety is a top priority, doors secured, no access to anything unsafe, and lots of supervised time. Whether I’m in your home or mine, your pet gets patient, reliable care with the goal of making them feel comfortable, understood, and well-loved.
“Renee is thoughtful and thorough and easy to have stay in our home to watch our old nervous pittie. He has a high sense of stranger danger and she has been so patient and careful with him every time we use her. Highly recommend her.”
About: I am currently a college student who loves animals. I have a dog and three cats at home, and I have volunteered at animal shelters in the past, so I’m very experienced with pets. While I am newer to house sitting, I am definitely not new to loving and caring for our furry friends! I work part time so I am available multiple times every day. I can stop by homes in the morning before work, and then after work in the afternoon and evening. I walk my dog and he loves our fenced in yard. I also am accustomed to feeding and cleaning litter boxes. And of course, care, love and attention are important every day!
“I’m very happy with the care my pitbull received. We had to leave town, and Valentina stayed with my dog in my home. She was punctual, responsible, and very attentive. My dog felt comfortable and relaxed in his familiar environment. I would definitely book with her again. Thank you!”
About: Dog lover with 10+ years of experience 🐶💛 I have my own American Akita he's 10 years old, so I know how to care for dogs with love and patience. I’ve trained and raised my dog myself, walked dogs for neighbors, and now I also work with small puppies at puppy yoga sessions🧘♀️✨ I’m friendly, loving and treat every dog like my own so your pup will feel safe, happy, and loved with me!🫶🏻 I currently have a part-time job, so I’m available on weekdays in the mornings until 2:30 PM, and again in the evenings after 5:00 PM. On weekends, I’m available on Sundays and can be flexible with timing. Your dog’s safety is always my top priority 🙏 I carefully follow all instructions from owners, including feeding, walking routines, and any special needs. I always keep dogs on a leash during walks and stay alert to the environment to avoid any stressful situations. I create a calm, safe, and loving space where your pet feels comfortable and secure. I pay close attention to behavior and make sure your dog is happy, relaxed, and well cared for at all times🤗❤️
About: Hi there! My name is Nicky (he/they) and I’ve been taking care of pets for my neighbors, friends, and family members for upwards of a decade and am commonly regarded as the go-to sitter in my community. I strive to treat every pet (and owner) with the utmost respect and kindness, and I’ll follow your instructions to a T! (The T stands for toe beans 🤓) Currently unemployed due to layoffs in my industry, so I’ll be able to give your fur bestie as much attention as possible! I can do overnights, multiple nights in a row, or just a drop-in/walk; whatever you need - I got you! :) I have a fenced yard in front of my apartment complex so your fur bestie can run free and tire themselves out before beddybye! I can crate your pup if you provide one or they can get some shut-eye on the couch or wherever they’re comfy!
Over 33 pet parents in Winnetka have booked house sitting
Winnetka pet parents share their Rover experiences
I was terrified about finding someone to watch my little Velcro baby. But Rebeca put me at ease. Her communication with me and love she gave my baby is beyond what I could have expected. I am so happy to have book with Rebeca and next time I am in Chicagoland I will definitely book with her again! Thank you Rebeca!!!
Madeline was fantastic! Our dog was immediately smitten with her. Not only was Madeline attentive to all of the instructions I shared with her, but she was also flexible when it came to scheduling, since we didn’t know how long we’d be gone for. I’d highly recommend Madeline as a responsible, dependable, and caring sitter for your pets!
Ella and her partner were terrific! I had to board my three month old puppy and was nervous about leaving her with someone so soon but the daily updates and pictures assuaged my fears! They were kind, patient and even gave me some training advice. I wouldn’t hesitate to use them again in the future. Georgie had a blast!
Rosy and Josh were excellent house sitters. They were great communicators with frequent updates on how Izzy was doing. They definitely gave her lots of love and attention while we were out of town. We could tell when we got back home that she was very comfortable with them and had a good time. We will definitely be asking them to house sit again for us. Thanks!
Jiayi was AMAZING with our pets!! We have a ZOO and she was so on top of everything. She sent photos and reached out with any questions and made me feel very comfortable having my fur babies in her care. I would recommend her to anyone. She’s really a gem. Thank you Jiayi!!! We will definitely use you again.
We cannot say enough good things about Ana! We hired her to house sit and pet sit during our vacation, and we were very nervous about leaving our five-month-old puppy for the first time. From day one, she made everything feel easy and completely worry-free. She kept us updated every morning and evening, sent lots of pictures, and clearly gave our puppy so much care and attention — plenty of walks, cuddles, and patient, expert handling of teething/nipping. It was also such a relief to have someone we trusted at the house to bring in packages and mail and let our cleaning crew in. We came home to a happy puppy and a house that was in the exact condition we left it (maybe even a bit cleaner!). Overall, an excellent experience — we’d hire her again in a heartbeat and recommend her highly.
Katelyn was timely and wonderful for popping in and taking care of the cats. She communicated well and dealt with any request we asked. We’re extremely grateful for her being prompt on a short notice. She followed instructions extremely well. We appreciate her effort.
As the owner of 3 dogs, Andrew is very knowledgeable about dogs. He immediately connected with our dog right when he walked in the door. Andrew took her outside and to the basement to get exercise and have some play time. He did a great job! I’d recommend him to any dog-owner for pet sitting.
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 Winnetka 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 Winnetka 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 Winnetka 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 7,807 house sitters in Winnetka. 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, 85% of Winnetka house sitters respond in under an hour.
House sitters in Winnetka have an average of 13 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 Winnetka.
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. Winnetka 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.
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