House Sitting in Winnetka
Find a loving house sitter to watch over your pets and your home.

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Loving house sitters in your neighborhood
The prices below are estimates per night for 1 adult dog, including fees. Pricing may vary based on your search.
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1. Leyla A.

“My cat needs especial treatment due to his urinary issue. Leyla did a great job, feeding him on time with the exact instruction I asked her plus the medication. I recommend her to ALL cat's parents!”


2. Molly S.


“Molly watched our two cattle dogs for a weekend away and we were so relieved to have someone who loves dogs so much and has so much experience. Our dogs warmed to her right away and we felt confident with them in her care.”


3. Grace P.

“Grace was fantastic! My elderly, medically fragile dog was in great shape when I got home. All the while, Grace sent photos and updates that eased my mind. It was a complicated regimen, and she got everything right! She was also very responsible about the key and other aspects as she stayed in my house. Couldn't be better, I highly recommend Grace!”


4. Janice M.

“Janice was fantastic! She sent photos and a daily report. I felt comfortable the entire time I was gone. Janice managed my pet's complex medical regimen as well. She left the house immaculate and my dog is very happy and calm -- she must have been a happy dog while I was gone! Thanks, Janice!”


5. shahrzad m.

“This is our second time booking Shahrzad, and we couldn’t be happier! She is absolutely wonderful, responsible, warm, and attentive. Our cats adore her, and we feel totally at ease knowing they’re in her care. She sends sweet updates and goes above and beyond every time. So grateful to have found her! She is our go-to cat sitter now!”


6. Emily B.
“Emily is a great pet sitter and exceptional dog walker. She is flexible, responsible, caring and pays attention to details. I highly recommend her for any pet care needs.”


7. Tamara K.

“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.”


8. Juliana M.

“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.”


9. Cecilia M.

“Cecelia was amazing!!! Was constantly in communication with me and sending me tons of photos of our cats! They definitely warmed up to her and seemed to enjoy her staying with them. I would definitely book her again next time we need someone to watch them :)”


10. Beray Z.
“Beray is a real animal lover. I’m her friend for 15 years and I can say with my whole heart that she can take the responsibility of caring or walking a dog. She begged for adopting one when she’s just 7 and took all the responsibility for her new child. When any parents of a dog wanted to go abroad or something, they counted on Beray because they knew their dog would have been happy with her even she was 10. I trust her and you should count on her too. She wouldn’t make you disappointed, I’m sure.”


11. Larry T.

“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.”


12. Kristin H.
“Simply wonderful!! Came back to a very happy dog- so many thx Kristin!”


13. Adeline R.

“Adeline was amazing!! She took care of my mini poodle while I was in town for a couple days and they had an absolute blast. Would highly recommend her!”


14. Robert K.


“Robert did a great job with our dog and our home. He sent updates on her during his stay. He took great care of our dog and our home. I would love for him to take of our girl again.”


15. Ericka S.

“Ericka was absolutely lovely. Our Olive warmed up to her right away and loved spending time with her. Ericka was extremely flexible with her time as I needed to make a couple changes since my travel plans were adjusted last minute. Definitely having Ericka back to stay in our home and take care of our Olive!”


16. Timothy M.

“Tim did a great job taking care of Pringle. He kept me updated with pictures throughout the day while I was at work which I appreciated. I can tell that she developed a bond with Tim and genuinely enjoyed her time with him. I’d definitely book him again and recommend him to anyone looking for a caring sitter.”


17. Eric W.
“Eric is a wonderful dog sitter. He has taken care of dogs for several years (German Shepherd, / Malamute / Husky / Rottweiler mix, Border Collie, and Coonhounds). He is firm, physically strong and compassionate. He has a knack for understanding dogs. He knows when they need a walk. He knows when they need their space. Eric is reliable, punctual and honest.”


18. Stacy H.
About: As a lifelong animal lover with experience caring for dogs, I'm confident in my ability to provide top-notch pet sitting services. Growing up with dogs and taking care of relatives' pets has taught me how to understand and connect with them. I'm passionate about making dogs feel loved, welcome, and comfortable, and I'm excited to bring my expertise and compassion to your pet. I work part-time with a flexible schedule, which means I always have time to care for dogs. Whether I'm working mornings or afternoons, I'll have plenty of time to give them the attention and love they need! Although I live in an apartment, there’s plenty of space for your pup to roam around. We have a small patio incase they like sunbathing.


19. Mannee M.

“Mannee came to our rescue for a last-minute Thanksgiving request and we couldn't have been happier. He has a wonderful presence that's very calming and we knew our baby was in good hands. Our dog is still learning to be comfortable with separation and Mannee handled him wonderfully. After he left, Kai stared at the door, dismayed that his new friend wasn't going to stay! Fantastic first Rover experience with Mannee.”


20. Viviana S.
“Viviana is really sweet, caring and patient. She helped me walk the dogs on with their daily walks, and also helped me feed them. I would definitely recommend!”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. 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 away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
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 Apr 2025 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 Apr 2025, there are 10,419 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.
