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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.”
“Iuliia was really great with our dogs Charlie and Pixie! She watched them for 3 nights at our home, and She sent us lots of pictures, videos, and updated us every day. We appreciate you watching them and caring for Charlie and Pixie! Thanks so much!”
“Molly was incredibly flexible & willing to work with us to make sure our 7 month old puppy was adequately cared for while we were in and out over the long weekend. She was attentive to our pup’s needs, and provided care as if our pup was one of her own!”
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.
“I could not have asked for a better care giver for our fur baby while we were out of town than Emily. My kitten does not do well alone and she stayed at our home with him and he took to her right away. She provided me with regular updates, was incredibly kind and responsive, respectful, and responsible. She was in ongoing communication with me and followed every ask I had. I would use her again in a heartbeat!”
“Great at communicating, sending photos and videos. There was one hiccup. In our opinion, best way to understand how good someone is is to see how they react to a situation. She was brilliant, organized and effective. Left the house beautiful and the pets happy. Will def use her services moving forward.”
“Could not ask for a sweeter kinder more knowledgeable sitter - it was a joy to have Julianna here and can’t wait for her to come back - our husky took to her the minute she wakes in the door !”
“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!”
“Larry was an excellent dog sitter for our pup. Our dog is a COVID dog and used to being with someone 24/7. Larry stayed at our house and walked, played and kept our pup company. He was able to bond with Mozzi the first day. We came home to a clean house and a very happy dog. We would definitely hire Larry again. So glad we found him on rover.com.”
“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. 🐶🙏🏻😍”
“We had a great experience with Nancy. She was very responsive from the start and kept us updated multiple times a day (with pictures) on how our dog was doing, which gave us a lot of peace of mind while we were away. Everything was left clean and tidy, and the whole experience felt very professional. We’d be happy to book with her again.”
“Sanaz took care of our two dogs with so much care while staying at our house. She also watched over our bearded dragon and three leopard geckos, making sure their lights were on and off when they were supposed to be and their water topped up. I would have her in our home again! I felt very safe with her care and attention to all. Thank you, Sanaz!”
“Daniela is incredible! She’s so communicative and sent so many cute photos and videos of my fur baby! My cat took to her very quickly and I was able to travel with peace of mind knowing she was getting the attention and playtime she needed while I was away!”
“Bouvier is an incredible sitter! She was wonderful with our senior dog and sent pics and texts to keep us updated. She completely put my mind at ease - I would 100% recommend her!”
“Ariana was amazing with our two pups! She is very kind & sweet. Amazing energy & the pups felt right at home with her. We felt very comfortable leaving her with the dogs and taking care of our home while we were away. We will definitely be using her as our pet sitter for all of our needs in the future! ?”
“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!”
About: I hope you can give me a chance to get to know your pet and provide passionate care and dedication. Thank you. 🐾🏡🩵 my experience: I have volunteered for over 4 years at an animal shelter providing kennel care, basic dog training, and walking. I took two years of vet science at Los Angeles Pierce college and can give oral medication, ear cleaning and nail trimming, and injections. I now have over a year experience of walking dogs big and small, in home visits and over night stays! after a difficult year healing from a uterine tumor, I have decided to dedicate my free time and strength to making dogs happy with fun walks and proper in home care + more! I’ve taken care of all dogs big and small in different environments- fenced yard, apartment, and pool. I know how to swim just incase of any emergency. The most dogs i’ve taken care of in one house is 3- a senior, puppy, and middle age.
About: Hello! I’m Anca, lover of all beings. While I am new to Rover, I am no stranger to pet sitting and care taking. Let’s meet! I have been fortunate to be surrounded by animals most of my life, and have an affinity for caretaking. I will attune to your loved companions’ needs with ease. I have experience with administering medications, including IVs, and preparing special diets. I am mindful of their movement, play and rest needs. While in my care, your pets will be doted on. I work remotely and have considerable flexibility in my schedule. I will strive to prioritize your scheduling needs, and I ask that we discuss this in advance. During house sitting I aim to spend most of my time within your home, and will communicate in advance my needs to steps away. I can often take your pets with me, if that’s suitable for you. I usually do not step away for longer than 5 hours during overnight stays. I’d be happy to discuss your exact scheduling needs in more detail when we meet. I would love to meet you and your beloved companions, and see if we are a good fit. If all systems are go, I’d like to collaborate with you to delineate a detailed and clear plan to meet your discussed expectations. I bring a calming presence to most animals, wild and domesticated. We will ensure that your pets get their daily needed activity, play, nurturance and rest. I’m keenly aware of my surroundings at all times, to ensure your companions’ safety. While in your home, I will respect your space as I do my own, and will aim to leave it better than I found it. I do ask that the space I am going to inhabit for the length of the stay, has clean linens, high speed internet and the home is well-maintained. I can be available as a person of contact for other maintenance services, for the duration of the stay, with advance notice and mutual agreement. I benefit greatly from concise notes on your pets’ needs and home expectations during overnight stays, for drop in visits or walks.
Over 160 pet parents in Winnetka have booked house sitting
Winnetka pet parents share their Rover experiences
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.
I appreciated Emily’s observational skills and calm response to my dog being sick while I was gone. She took good care of her and used good common sense in caring for our dog. Our dog was happy and seemed fully recovered when we returned home. The house was clean and she went beyond to make sure everything was back to normal when we returned. Thank you.
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 $65
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 $65 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 10,667 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, 83% of Winnetka house sitters respond in under an hour.
House sitters in Winnetka have an average of 14 years of experience. 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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