House Sitting in Winnetka
Find a loving house sitter to watch over your pets and your home.
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Top rated Winnetka house sitters
“Andrew stayed in our home for a week He took good care of the litter boxes snd was respectful of the space. His very laid back, “chill” demeanor was perfect for our 2 cats. Andrew was very also observant and in tune with their needs and moods. He contacted me on a regular basis and sent me photos of his little charges. We intend to use his services again and highly recommended him to anyone in need of a cat sitter.”
“Emily is an excellent sitter. My little crew is not the easiest to handle. While my cat is incredibly entertaining, she's not exactly cuddly, she just wants to get into as much mischief as possible. My dog is a beautiful sweet boy with anxiety issues. He really requires the right energy or his anxiety becomes aggravating (he barks excessively, chews inappropriately and paces). Thankfully, Emily's calm demeanor helps put him at ease. Throughout her stay Emily communicated regularly with plenty of pictures to share. She left my home neat and clean. I will use Emily again without hesitation.”
“Jason was great - he was kind enough to meet our dogs before his stay and took care of them while we were gone for a few days. Our home was spotless upon our return. Thanks, Jason!”
“Omg. I cannot possibly say enough about how amazing Ella was with our very senior dog. She Went so far above and beyond to accommodate our dogs needs. Meds, cooking, walks, love. Dealt with a bad doggie belly, kept us totally informed the whole time we were gone and did everything and then some to make our dog feel loved and comfortable. We could never have taken our trip without her. She is a wonderful person as well. When we got home the dog was happy, the house was clean and we got to enjoy a trip. Such a gift and we will 100% be using her services again. ????”
“It gave us such piece of mind to have Olivia send us updates and photos of our Lacey while we were out of town, especially since we were overseas. Lacey was very calm when we returned. So grateful!”
“Donna and Stephen were great! It was our first time leaving our energetic puppy and they quickly put my mind at ease about leaving him. We came back to a happy puppy and cat and a clean home. We appreciate how well they cared for our fur babies and respected our home. Wouldn’t hesitate to book them again!”
“We will absolutely use Michelle again! She took great care of Teddy and our home during a trip away. She provided plenty of updates and photos and was responsive. Thanks for everything!!”
“By far & away Coty was THE BEST dog sitter/house sitter I've ever had. She was incredibly responsive and communication cadence was exactly as I like. She sent me a daily update including pictures and video. She was extremely organized, asked all the right questions in preparation for the stay. The best part was coming home to my home cleaner than I left it. If I could give Coty 10 stars I would! Will definitely use again!”
“Amelia is a wonderful dog sitter. We just returned from a week long trip and Lulu seems super happy. Amelia sent us photos every day along with a little blurb about how things were going. The house is clean, Lulu’s water is fresh and we’re relieved to have had a wonderful, nice and interesting person stay, who’s actually a writer in her spare time.”
“Marcus is the sweetest; he is so kind and caring. He really went above and beyond for our pets, our home and our family while we were away. We had a lot of rain and Marcus walked our dog throughout the day so he could get enough activity without getting muddy in the yard. He was also patient and sweet to our very shy cat. My home looked better when we got back then before we left! Excellent communication as well! Thank you Marcus!!”
“Gretchen was super sweet and nice! She sent me pictures whenever I asked for them and I came home to a very happy doggy! She even hand sketched a beautiful picture of my dog Daisy!”
“Chris was great. She was professional and awesome with my dogs. She gave plenty of updates and i never had to worry about my dogs while I was away. I will be using her again.”
About: I provide loving, reliable care tailored to your pets needs! With experience in house sitting, dog sitting, and caring for my own fur babies throughout the years, I understand the importance of trust and personalized care. Whether it’s energetic playtime, gentle senior care, or sticking to a routine, I’ll make sure your dog feels safe, happy, and loved while you’re away. As a teacher, my summers and weekends are flexible, giving me plenty of time to provide attentive, loving care for your pup. Whether it’s daily walks, playtime, or overnight stays, I’ll make sure your dog gets the care and attention they deserve! "I provide personalized, attentive care whether in my home or yours! In your home, I ensure your pet sticks to their routine, offering plenty of love, exercise, and companionship. I keep their space clean, follow feeding and medication schedules, and provide regular updates for your peace of mind. If caring for pets in my home, I create a safe, comfortable environment with plenty of playtime, cuddles, and enrichment to keep them happy and relaxed. No matter the setting, your pet’s well-being and happiness are my top priorities.
“Thank you for your services. Mia is great, she provided me with updates and photos! We did a meet and greet beforehand, Prada was very well taken care of. She even washed some of my dishes and took trash out. Thank you again, we will be looking forward on seeing you again! 10/10”
“Scott took such great care of our two pups when we were out of town. We are so grateful we were able to book his services at the last minute. We got consistent updates on how our pups were doing while we were gone and we could tell they were nice and relaxed and were able to spend a lot of their time outside. We really hope to book his services again soon!”
About: Just a medical student with a lot of time on my hands. People trust me with their health, I promise I will take great care of your furry children. If by chance one of your pets has any medical needs, i.e. shots or pills, I would be more than happy to help. My own family has two dogs and two cats. I have no biases against any dog breed. I promise to keep your house clean and be punctual. You should not have to worry about accidents while you are away. Thank you for your consideration of me. I have an open schedule for the end of March and April. May will be mildly reduced, but I am flexible and available to speak. Bother services I offer. I am available for overnight stays and long walks if necessary. I do not bring my dogs with me to any services.
“Natalie watched our 2 dogs while we were out of town and was wonderful. We have a shy chihuahua and a special needs bulldog so they are a handful/aren’t the most fun for other people to watch. Natalie did great with them, was very communicative which made us feel very at ease (we were nervous going into it) and sent us pictures every day. It’s the first time we’ve gone out of town and come home to our bulldog not being a total disaster and needing to go to the vet immediately which was awesome!”
“Bridget was the best dog sitter we have ever had (that is saying a lot because we have had him for 11 years)! She communicates with us the whole time and sent a ton of great photos. Our dog has some special needs (arthritis and doesn’t love other dogs) and she handled it perfectly. We will book her for all future vacations and dog walks.”
“Anna was an amazing dog sitter for my pup, Harvey, while I was away for a week. She stayed in my home and was a sublime guest. She even cleaned her own towels before leaving (which was totally unnecessary!) I never would have known someone was here. She sent incredible detailed updates daily, including photos, and took him out for very long walks daily. He was VERY spoiled by her! She was also very communicative with me about when she'd be gone from my house and when she'd be back, which I appreciated greatly. I'd highly highly recommend Anna and I definitely plan to call her again!”
“Grace was excellent! She checked in regularly, sent lots of pics of Tini and genuinely cared about Tini and her comfort (she's a Senior dog). Grace was respectful of our home and we came home to a clean house, she even washed and folded the sheets she used. We will definitely use Grace again, Tini was very well cared for! Thank you Grace!”
Loving house sitters in your neighborhood
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1. Andrew N.
“Andrew stayed in our home for a week He took good care of the litter boxes snd was respectful of the space. His very laid back, “chill” demeanor was perfect for our 2 cats. Andrew was very also observant and in tune with their needs and moods. He contacted me on a regular basis and sent me photos of his little charges. We intend to use his services again and highly recommended him to anyone in need of a cat sitter.”
2. Emily G.
“Emily is an excellent sitter. My little crew is not the easiest to handle. While my cat is incredibly entertaining, she's not exactly cuddly, she just wants to get into as much mischief as possible. My dog is a beautiful sweet boy with anxiety issues. He really requires the right energy or his anxiety becomes aggravating (he barks excessively, chews inappropriately and paces). Thankfully, Emily's calm demeanor helps put him at ease. Throughout her stay Emily communicated regularly with plenty of pictures to share. She left my home neat and clean. I will use Emily again without hesitation.”
3. Jason A.
“Jason was great - he was kind enough to meet our dogs before his stay and took care of them while we were gone for a few days. Our home was spotless upon our return. Thanks, Jason!”
4. Ella V.
“Omg. I cannot possibly say enough about how amazing Ella was with our very senior dog. She Went so far above and beyond to accommodate our dogs needs. Meds, cooking, walks, love. Dealt with a bad doggie belly, kept us totally informed the whole time we were gone and did everything and then some to make our dog feel loved and comfortable. We could never have taken our trip without her. She is a wonderful person as well. When we got home the dog was happy, the house was clean and we got to enjoy a trip. Such a gift and we will 100% be using her services again. ????”
5. Olivia V.
“It gave us such piece of mind to have Olivia send us updates and photos of our Lacey while we were out of town, especially since we were overseas. Lacey was very calm when we returned. So grateful!”
6. Donna C.
“Donna and Stephen were great! It was our first time leaving our energetic puppy and they quickly put my mind at ease about leaving him. We came back to a happy puppy and cat and a clean home. We appreciate how well they cared for our fur babies and respected our home. Wouldn’t hesitate to book them again!”
7. Michelle M.
“We will absolutely use Michelle again! She took great care of Teddy and our home during a trip away. She provided plenty of updates and photos and was responsive. Thanks for everything!!”
8. Coty C.
“By far & away Coty was THE BEST dog sitter/house sitter I've ever had. She was incredibly responsive and communication cadence was exactly as I like. She sent me a daily update including pictures and video. She was extremely organized, asked all the right questions in preparation for the stay. The best part was coming home to my home cleaner than I left it. If I could give Coty 10 stars I would! Will definitely use again!”
9. Amelia S.
“Amelia is a wonderful dog sitter. We just returned from a week long trip and Lulu seems super happy. Amelia sent us photos every day along with a little blurb about how things were going. The house is clean, Lulu’s water is fresh and we’re relieved to have had a wonderful, nice and interesting person stay, who’s actually a writer in her spare time.”
10. Marcus T.
“Marcus is the sweetest; he is so kind and caring. He really went above and beyond for our pets, our home and our family while we were away. We had a lot of rain and Marcus walked our dog throughout the day so he could get enough activity without getting muddy in the yard. He was also patient and sweet to our very shy cat. My home looked better when we got back then before we left! Excellent communication as well! Thank you Marcus!!”
11. Gretchen K.
“Gretchen was super sweet and nice! She sent me pictures whenever I asked for them and I came home to a very happy doggy! She even hand sketched a beautiful picture of my dog Daisy!”
12. Chris C.
“Chris was great. She was professional and awesome with my dogs. She gave plenty of updates and i never had to worry about my dogs while I was away. I will be using her again.”
13. Rachel H.
“Saying Rachel is the best would be an understatement for what she does. My Bichon Frisé, Princess, absolutely adores Rachel, and she whines when she sees her go. Rachel is the safest person that you can trust with your fur baby. I highly recommend that you consider her for your family!”
14. Mia E.
“Thank you for your services. Mia is great, she provided me with updates and photos! We did a meet and greet beforehand, Prada was very well taken care of. She even washed some of my dishes and took trash out. Thank you again, we will be looking forward on seeing you again! 10/10”
15. Scott J.
“Scott took such great care of our two pups when we were out of town. We are so grateful we were able to book his services at the last minute. We got consistent updates on how our pups were doing while we were gone and we could tell they were nice and relaxed and were able to spend a lot of their time outside. We really hope to book his services again soon!”
16. Katheryn S.
“Katheryn would make an exemplary dog sitter for Rover and has a proven track record of taking great care of animals (her own and others) and I cannot recommend her enough to others looking for a responsible and loving caregiver for their dog. Katheryn has been taking care of animals for the majority of her life. At first, the responsibilities were simple and limited to taking care of just her one cat, but the family has since grown and extended to include multiple cats and dogs in the house. With years of experience under her, she has also been a dependable caretaker for my dog Ted as well. I can trust leaving Ted with her and rest easy knowing that his needs are all being met and then some (nice long walks, extra treats, and cozy, warm snuggling)!”
17. Natalie C.
“Natalie watched our 2 dogs while we were out of town and was wonderful. We have a shy chihuahua and a special needs bulldog so they are a handful/aren’t the most fun for other people to watch. Natalie did great with them, was very communicative which made us feel very at ease (we were nervous going into it) and sent us pictures every day. It’s the first time we’ve gone out of town and come home to our bulldog not being a total disaster and needing to go to the vet immediately which was awesome!”
18. Bridget N.
“Bridget was the best dog sitter we have ever had (that is saying a lot because we have had him for 11 years)! She communicates with us the whole time and sent a ton of great photos. Our dog has some special needs (arthritis and doesn’t love other dogs) and she handled it perfectly. We will book her for all future vacations and dog walks.”
19. Anna D.
“Anna was an amazing dog sitter for my pup, Harvey, while I was away for a week. She stayed in my home and was a sublime guest. She even cleaned her own towels before leaving (which was totally unnecessary!) I never would have known someone was here. She sent incredible detailed updates daily, including photos, and took him out for very long walks daily. He was VERY spoiled by her! She was also very communicative with me about when she'd be gone from my house and when she'd be back, which I appreciated greatly. I'd highly highly recommend Anna and I definitely plan to call her again!”
20. Grace R.
“Grace was excellent! She checked in regularly, sent lots of pics of Tini and genuinely cared about Tini and her comfort (she's a Senior dog). Grace was respectful of our home and we came home to a clean house, she even washed and folded the sheets she used. We will definitely use Grace again, Tini was very well cared for! Thank you Grace!”
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!
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 $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 Apr 2025, there are 6,570 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, 84% 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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