House Sitting in Winnetka

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed availability
Thanksgiving
1. Hillary Verified Background Check

Home Full-Time/Flexible Dog Lover

Rogers Park, Chicago, IL, 60626

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Hillary was great! Kept me updated throughout the night with pictures and really made me feel comfortable that my pup was in good hands. Would and will hire ... (more)"

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2. Molly Verified Background CheckRover 101

Wags & Kisses!

Highland Park, IL, 60035

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Molly was amazing with my dog! She was very responsive to all of my texts while I was away and my dog had a great time with her! She’s also very punctual and... (more)"

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3. Rachel Verified Background Check

Full time animal lover!

Evanston, IL, 60201

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Rachel was fantastic with our old pups! She kept us informed and sent us pictures. It was obvious that they got a lot of love and attention and were happy to... (more)"

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4. Tanya Verified Enhanced Background CheckRover 101

Compassionate Caretaker

Evanston, IL, 60201

House Sitting, Drop-In Visits, Dog Walking

"Tanya was amazing! She was able to make me feel comfortable leaving my 19 year old kitty who requires daily IV medications and 2 other cats for a couple of d... (more)"

5. Brooke Verified Background Check

Grad student and adventure seeker

Skokie, IL, 60077

House Sitting, Drop-In Visits, Dog Walking

"Brooke watched our dog, Sonny, for five nights and six days while my husband and I were out of the country and we knew Sonny was in good hands the whole time... (more)"

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6. Alanna Verified Background Check

Cuddle Expert!

Evanston, IL, 60201

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Alanna was amazing! She was really easy to work with and took great care of our pup providing lots of updates and pictures. You can tell she really loves an... (more)"

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7. Ryan Verified Background Check

Trusted, Reliable, Flexible.

Wilmette, IL, 60091

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Ryan is terrific! He house sat for us for five days and took wonderful care of our elderly dog and cat. Ryan was super responsive and kept us informed of how... (more)"

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8. Brittany Verified Background Check

I love pups as much as they love me

Morton Grove, IL, 60053

House Sitting, Drop-In Visits, Dog Walking

"Brittany would be a great dog sitter as she at one time had three golden retrievers, whom she adored, and took great care of. She loves animals, and is a ve... (more)"

Confirmed availability
Thanksgiving
9. Audrey Verified Background Check

I’m a full time mom

Winnetka, IL, 60093

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"We had very great experiences with Audrey, who helped us tons of times when in need. She is such a nice, gentle and patient sitter that you could see from he... (more)"

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10. Kyla Verified Background Check

Genuine and experienced pet sitter

Evanston, IL, 60201

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Kyla is a loving and responsible sitter. (more)"

11. Lena Verified Background Check

Fun, reliable, lover of animals!

Evanston, IL, 60201

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"She is awesome! Dogs were super happy upon return. Will rebook! (more)"

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12. Alyssa Verified Background Check

Experienced Dog Sitter Available

Highland Park, IL, 60035

House Sitting, Drop-In Visits, Dog Walking

"Alyssa was incredibly responsive and helpful when my wife and I were in a pinch and needed to leave town within about 48 hours. She was careful to ensure she... (more)"

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13. Maya Verified Background Check

Cats are my thing!

Skokie, IL, 60077

House Sitting, Drop-In Visits, Dog Walking

"Maya is a wonderful caretaker for her cats. She has been there for every moment of their lives and has been able to make them feel comfortable and calm. From... (more)"

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14. Rachel Verified Background Check

loving care while you’re not there

Evanston, IL, 60201

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Rachel hit it off right away with our pup. We could tell that she adores dogs & the two of them got close very quickly. She is very responsible & would love ... (more)"

15. Ethan Verified Background Check

Avid dog lover with flexible hours

Evanston, IL, 60201

House Sitting, Drop-In Visits, Dog Walking

"Ethan was an awesome dog walker and caretaker of my dog Rocco when we went on vacation. He checked in with us every day and sent amazing photos and videos s... (more)"

16. Diana Verified Background Check

I'll be your dog's best friend!

Glencoe, IL, 60022

House Sitting

"Diana was amazing with our two mini dachshunds while we were away for a weekend trip. She was fantastic with keeping in touch with us while we were away wit... (more)"

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17. Paul Verified Enhanced Background CheckRover 101

I will run with you dog

Evanston, IL, 60201

House Sitting, Drop-In Visits, Dog Walking

"Paul is simply amazing. He treats Stat as if it was his own. I get frequent updates, photos and videos and see how Stat is truly enjoying his company. I've u... (more)"

18. Samantha Verified Background CheckRover 101

My friends call me a Dog Whisperer.

Wilmette, IL, 60091

House Sitting, Doggy Day Care

"Samantha took great care of my pup! My pup was in such high spirits when I came home thanks to samantha! Definitely booking with her again in the future :) (more)"

19. Emily Verified Background Check

Caring, Flexible, Dogwalker.

Glencoe, IL, 60022

House Sitting, Drop-In Visits, Dog Walking

"No one loves dogs more than Emily. She has experience walking more than one dog at a time. Anybdog eould be lucky to have her as their walker. (more)"

20. Aracely Verified Background Check

Dog lover!

Winnetka, IL, 60093

House Sitting, Drop-In Visits, Dog Walking

"Aracely was everything I wanted in a dog sitter, friendly and reliable. Traveling a lot for work means I am often away from my dog. Leaving your pet with som... (more)"


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Winnetka house sitting needs. On Rover, it's easy to find a loving dog sitter in Winnetka who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Winnetka house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Winnetka for your dog — people who'll treat him like family.