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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%.
“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.”

“Jeanette has watched my dog three times now and she is absolutely amazing! My dog loves her and she always takes such good care of my dog. She is great about sending updates, pics and is very response/respectful to all my questions/requests. Jeanette is also very respectful of my home and goes above and beyond when she stays...she cleaned up (even though I told her she doesn’t have to). She is absolutely amazing and I can’t recommend her enough”

“Daniela was great with our puppy and our senior dog as well as multiple cats and birds when she house sat for us. We got lots of pictures and updates and could see the progress she was making in teaching the puppy to heel on walks. She went above and beyond to keep things organized and clean, which is not easy in our chaotic household. She even got our most timid cat to come out of hiding for treats. We’ll be booking Daniela for our next trip if at all possible.”

“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!”


“Gyselle is a fantastic dog sitter. She’s very responsive and takes care ofPringle, as if she were her own. I’m a regular client of hers and I never have to worry when Pringle is in her care. Highly recommend.”

“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!”

“Jeremy was great with our boys! They can be quite the handful but we came home to two happy and tired pups! He communicated well thru the whole stay and sent plenty of pictures!! We already have our next house sit with him scheduled 😊”

“This was our second time having Ariana sit our cats and she did an amazing job. She offered a complementary home visit to meet the cats which was great for getting them familiar with her prior to us leaving. She was very attentive and communicative so we never worried or had to wonder about how they were doing. We can tell our cats really enjoyed her company. Would definitely book with Ariana again!”
About: I have grown up with nothing but animals from cats, dogs, farm animals, you name it! I have experience grooming dogs and love what i do! I set myself different because I have a way of building up bonds with every single one. Im very responsible and will take care of your pets needs, and get their required exercise. I'll be able to impress all pet owners in my great attitude and skills. I will be able to work along side your sweet pet and get them to trust me :). Working with animals would help my improve so well for the future, because I am looking forwards into being a vet, one of my long time dreams, and this would help me very much. I hope to see you all soon Thank You ! I currently aspire to do my own schedule at my own pace and time. I personally have a different passion for animals than others. I care about every individual animal and don't discriminate against any kind of pet! I also do school, so this kind of individual routine is the best case! I have such a great instinct and can read dog and cat body language very differently. I also can crate if needed and have friendly cats who can also be put away if you are not comfortable!
“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!”

“Christian is everything we could ask for in a house and pet sitter for our Velcro dog and cat. He followed all of our care instructions, and he was communicative and responsive. Christian tuned in immediately to our dog’s schedule and needs, and provided emotional the emotional support that she requires while we are away. I cannot recommend Christian enough as a house/pet sitter!”

“Erika was wonderful! She took such good care of my girl (Rosie - a golden doodle)...took her on walks, watched movies with her (my dog loves to cuddle and watch tv), played with her and more. Erika stayed at my house for five days while we were away on vacation and kept it clean and nice - even washed sheets and towels (something extra!). Erika is responsible and dependable and am booking her for a lot more assignments! Thank you, Erika!”

“Lexi is great to work with. Definitely had a great experience with her and my dogs loved her :) I have 2 Rottweilers and initially I was iffy about this because they’re bigger dogs but she was able to handle them with love and care 😁 will be definitely re booking her from here on out”

“Maryna, is very caring and she is prompt, she informs me about all the activities that Buddy, does; pictures, walks, feeding time everything and she is very reliable. I would strongly recommend Maryna to my family and friends...!”


About: I’ve grown up with caring for multiple types of pets ranging in many different breeds and personalities, I’ve done pet-sitting for neighbors, friends and family multiple occasions and would love to show your pet what lots of love and attention feels like from someone that has extra to give ☺️ I have a big heart and always love to see what I can do to improve you and your pets day! As of right now I am working freelance jobs on Monday-Fridays with random days off. On Monday-Fridays, I am free before 9am and after 630pm, Weekends I am always off with full availability at the moment. I have a big heart to shower your pet/pets with love! I have a 2yr old dog of my own that is trained and respectful so if your pet enjoys company of a friend I’m sure they’ll have a blast, I also can keep him separated if requested for more personal space for any animal needs :) I am a very attentive sitter ready to give you more time to get things done or even do the small tasks that you just don’t have time to squeeze in the day, let me help you make the day easier for you😊!
“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!”

“Tamara was such a wonderful dog sitter for our sweet boy, Wallace. She was very communicative and sent so many cute videos and photos!! She even made a trip to TJ Maxx for some blankets for our boy, to help alleve some of his anxiety. We appreciated her so much and would absolutely have her stay over again.”

Over 153 pet parents in Winnetka have booked house sitting
Winnetka pet parents share their Rover experiences
We were so impressed with Lexi! She was incredibly attentive to our dogs, checking in with us frequently and keeping us updated the whole time. She took detailed notes on their routine and followed them faithfully, which made a huge difference — our dogs clearly felt comfortable and loved her from day one. Reliable, caring, and professional; we couldn’t have asked for a better sitter and will happily book her again. Highly recommended!

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!

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!

Ava is what every dog owner hopes for when leaving their pet in someone else’s care. She is loving, gentle, trustworthy, and we couldn’t be more grateful to have found her. Clover is a shy and nervous but sweet girl who just takes some time to open up- but Ava’s unmatched ability to make her feel adored and safe has meant an easy transition to being best buds. Whether it’s taking clover for her daily walk, or Ava watching her for an extended stay, we take comfort in knowing our girl is being loved and having a blast.

Gabriella was absolutely amazing at taking care of my Amstaff. I was away for the holidays for a couple of weeks, and very anxious, but Gabriella helped to ease that worry. She gave me daily updates, followed instructions, and played with Saint (my dog) every night! I will definitely be hiring her again in the future

Absolutely outstanding care of my young rescue. Jasmine took the time to come to my home before the actual sitting date to ensure it would be easier on my dog when staying with a new person. Jasmine stayed for close to an hour until my dog calmed down and engaged in play with her. She brought her own treats. My dog adores her and I will definitely request Jasmine in the future.

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 Mar 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.
As of Mar 2026, there are 10,716 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.










