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Top rated Winnetka house sitters
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Jeni is a talented, trusted, handler. She is kind, patient, punctual, honest, friendly, fun, and extremely loving. I can’t possibly express how grateful I am to have Jeni help me with my precious dogs. Her expertise, patience and knowledge have added so much to their lives. They both enjoy-walks, playtime, socialization. My dogs, Brutus (6 year old male Pekingese) and Rambo (1 year old male pug mix, rescue, are thrilled when Jeni comes to take them for their walks, and play dates. Rambo is very shy and panicky. Jeni takes as much time as needed to let Rambo settle which is within seconds. Brutus loves everybody so he and Rambo enjoy their time with Jeni tremendously. Highly, highly, recommend Jeni. I welcome any questions.”
About: Hey, I’m Anthony! I’ve been around animals since I was born. Grew up on a mini farm and took care of countless of dogs, as well as cats. I actually have a Siamese cat! I’ve always felt so connected with animals my entire life and most (if not all) pets of friends/family love me :) I’ve also watched a lot of pets in my life from time to time, whether it’s for a friend, neighbor, or family member. I work part-time at the moment and I have a lot of time on my hands, aside from work and occasional hobbies. My work schedule is given out a month in advance, so I always know when I’m available in the future and when I’m not. I’m very good with respecting the boundaries of animals and providing the care that they need. Your animal needs a lot of playtime? I got that covered. Your animal needs company but is more on the shy side? Got it, we can just hang out! Let me know what is needed for your pet, how their usual day looks, and I’ll be more than happy to put my all into caring for them
“IULIIA is a great dog watcher! We have hired her on 3 different occasions and are very happy with her. I highly recommend her! We will use her again for sure. Thank you!”
“Kim was great with Sadie! She played with her and took her on a walk. Sadie is a very high energy dog. Kim did a good job keeping her busy. Sadie really enjoyed spending time with Kim. We will definitely contact her again.”
“Shanneal is a fantastic sitter - she took care of our two puppers, one of whom can be challenging and needs some specific care, for a couple nights at our house. She sent lots of pictures and did a great job making sure the doggies were happy. Highly recommend!”
“She was fabulous. Very sweet and took great care of our little puppy. Even right after his neuter surgery. She took photos and videos throughout the night. Very polite.”
About: I have 3 dogs at home, two small and one large. I have had dogs all my life and I am comfortable with dogs of all breeds and sizes! I understand the importance of the first time meeting a dog and will be patient until they feel comfortable around me. I have worked with rescues before saving dogs from the streets which is where I learned a lot of my dog skills as well. I love my walks with my dogs and would love to walk yours! I do currently work full time but I am available after 5:00 PM Monday - Friday and all day on the weekends. I hope to get to meet your dog or dogs soon! I currently work full-time but am available for evening walks after 5 PM on Monday - Friday. On the weekends, I am available all day! I have experience dog sitting and always follow the instructions the owner has left for me. I am a guest in the home and always make sure I am on top of all my duties. I triple check everything is the way it should be prior to heading out the door to ensure the comfort and safety of my clients pet.
“Molly took good care of my pups and has excellent communication skills. She kept me in the loop the whole we were out of town, sent photo updates and my house was spotless. Highly recommend!”
About: I've had all ranges of animals from dogs, cats, fish, turtles, and bunnies, and even worked on a farm in high school! I love all animals and am passionate about their care and well-being, and they are my happy place. I have experience in caring for senior animals and babies as well. I have pets at my home, so I am always around animals and care for them daily. I can take care of pets outside of my job pretty much anytime since my schedule fluctuates and I work part-time as well, so I can be flexible towards your needs! :) I make sure the animals have food and water and enrichment time, which is essential for their development and mental stimulation! Making sure to take my dogs to the dog park or playing fetch with them outside, and my cat also likes to play fetch too indoors, and she loves her cat boxes and cat trees! Providing for them is what I do with my life! I pretty much work for them lol
About: Hi all! My name is Geena and I am a recent graduate from UCSC! I’ve taken care of and lived with German Shepherds my entire life. From mid sized dogs to fluffy monsters, I don’t shy away from pets. I previously owned a dog that was both blind and deaf so I am aware of how to approach a special needs pet. I’m looking to walk dogs and engage with my community more. Hope to see you soon! As a post-grad student navigating the challenges of full time employment, I’m looking to get out in the evenings for some enrichment. I’m hoping that I can help enrich your animal and help boost its mood, just like I know being with them will aid mine! Being raised with German Shepherds has taught me the importance of patience and understanding how much energy dogs may have. I’m hoping to help exert your dog’s energy all while exploring the community more! At home, I keep my dogs collared at all times, ensuring their safety. On walks, they will remain leashed, collared, and will always be under constant supervision. I will care for your pets and take caution just as they are my own. I understand how scary it may be to trust a stranger but, I’m happy to help alleviate any stress for all parties involved.
“Gillian takes great care of Pringle while I’m at work, and I really appreciate how punctual and responsive she is. I feel at ease knowing Pringle is in good hands, and I definitely plan to be a regular client!”
“Ariana stayed at my house to watch my two dogs and was tremendous. She’s trustworthy, good communicator, loves animals, and responsible. I’d give 6 stars if I could and look forward to using her again!”
“We just did our first overnight stay with Daniela watching our two dogs and one cat. She was fabulous! We’ve never been comfortable leaving our dogs because they have some weird quirks — and one is quite reactive on walks — but she was a true pro and handled everything beautifully. We got lots of updates and photos and all the animals were very happy. She also went above and beyond to wash the sheets before leaving! We’ve definitely found our go-to sitter.”
“I definitely recommend Ethan! I booked Ethan for a few hours to stay with my sensitive new rescue dog Monty when I had to leave for work. Monty is still decompressing and gets stressed and barks when left alone. Ethan was very patient with him and even got Monty to warm up so much he was asking for belly rubs!”
“Taylor was really patient with Luna, and built a relationship with her overtime. We are so grateful to have found Taylor and recommend her to others. She is a welcome addition to the pack! 🐾”
“Alondra took a good care of my dog for 3 days that I was out of town. It was my first time leaving my dog with someone other than family and she loved Alondra . To me it was very important that my dog feels safe and not anxious when I’m out for few days and I’m glad I found Alondra that could stay with TaTa at my place so TaTa felt so relaxed. 🐶🙏🏻😍”
“I needed a last minute sitter for my wedding day and Juliana responded so quickly. She was able to pick my dog up from the hotel and sent me updates all throughout the day. She kept my pup happy and I couldn’t be more thankful for her services.”
Winnetka pet parents share their Rover experiences
Jesse was such a great help to me in taking care of my dog when I was setting up a party. My dog was a bit anxious and overstimulated from all my running around while doing party prep and Jesse helped calm him with cuddles and reassurance. It was a relief to not have to worry about my dog during my party because I knew he was in great hands.
Bouvier was above and beyond communicative and caring of our 2 senior Golden Retrievers, one with medical needs and the other that developed a medical need while we were gone. We felt in the loop the entire time although we were a Continent away. She took over sitting in between another sitter’s stay and was more than willing to communicate personally with her about the status of the pups. We are grateful to Bouvier and look forward to having her our pups in the future.
It was such a joy to have Geena pet/house sit for us! We had to leave for a week for a family memorial service and couldn't have been happier with her care for our dog and cat (and python)! She really went above and beyond to give our pets plenty of love, play, and attention, and was great about giving plenty of updates. Love that she was super transparent about all our pets' behavior while we were gone, letting us know when they ate or didn't eat, how our dog was on walks, etc. Above all, you can tell she really loves animals, and we'd be more than happy to have her watch our babies again in the future!
Taylor is amazing. She was wonderful with our dogs, who she willingly got to know prior to our trip. They immediately bonded with her, even tho one of our dogs is usually slow to connect with new people. She is super responsible and always communicated with us on a daily basis while we were gone. She also took good care of our home and plants. We highly recommend Taylor!
This is our second time using Emily and she is just fantastic! I cannot recommend her enough, she is so caring and thoughtful and provides such excellent care for our fur baby. She sends daily updates and pictures and also took great care of the house since we had her stay at the house for the duration of our vacation as well. Highly trustworthy and responsible, we would continue to use her again every time!
Cynthia watched my dog, Rocco, at my hotel while my husband and I went to dinner and a concert. She was very flexible about coming to our hotel. Cynthia had great communication and made me feel reassured that Rocco was in good hands. She sent texts and photos throughout the night. She took Rocco for a couple walks and fed him dinner. I would definitely recommend her others and will select her again the next time we are in Las Vegas.
Sanaz took wonderful care of our two dogs and two cats while our family was away on vacation. Her communication was always prompt whenever we had a question or wanted to check in. She sent several photos / videos each day and helped administer medication for our cat. I definitely recommend Sanaz as a trustworthy and caring pet / house sitter.
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 $63
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 3 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 $63 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.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 89% of Winnetka house sitters respond in under an hour.
House sitters with repeat customers have an average of 3 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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