Pet Sitting & Drop In Visits in Winnetka, IL

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

1. Susan

Full time Dog Mom has luv to share

Wilmette, IL, 60091

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

10 repeat clients

"Susan is awesome! Very flexible and responsive! She did a great job with our boys and we would have her back any time. (more)"

2. Mary

Reliable and patient dog whisper

Evanston, IL, 60201

Drop-In Visits, Dog Walking

2 repeat clients

"Mary is a great walker and pet friend! When we need someone to look after our two pups she’s without a doubt our go to. She’s patient and a genuine pet lover... (more)"

Confirmed Memorial day Availability
3. Donna

Longing for fur on my clothes!!!

Northbrook, IL, 60062

House Sitting, Drop-In Visits, Dog Walking

"I highly recommend Donna as a caregiver for your furry friends. Donna is an animal lover. She is very knowledgeable about animals and I am confident she will... (more)"

4. Kristi

I'm a good doggy conversationalist

Evanston, IL, 60201

House Sitting, Drop-In Visits, Dog Walking

"Kristi is so sweet and reliable. She naturally has a love for dogs and is so playful with them! She is easy to get in contact with and accommodating to your ... (more)"

5. Emily

Infinite love & time for your dog!

Wilmette, IL, 60091

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Emily was nothing less than a blessing for a last minute booking when we had to go away for a day. She made three drop in visits to feed, exercise, and keep ... (more)"

6. Jonathan

home full time - large yard

Kenilworth, IL, 60043

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Jonathan goes WAY above and beyond what is expected! My dog didn’t even care if we came home or not! She was hoping for her best buddy, Jonathan. -Allan (more)"

7. Liz

Your Dog is like My Dog in our Home!

glenview, IL, 60025

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

39 repeat clients

"Liz came to our home to feed and let the boys out. All appears to have gone well. Liz sent pics of the boys outside, which was great! We have her booked t... (more)"

8. Agnes

What have we done to deserve dogs?

EVANSTON, IL, 60201

House Sitting, Drop-In Visits, Dog Walking

"Agnes loves dogs so much it's apparent whenever she meets one. Her energy and enthusiasm are unparalleled when it comes to dogs. She is responsible and trust... (more)"

Available this weekend
9. Joseph

Vegan who loves all animals

Evanston, IL, 60201

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Oh my gosh! Joe is fabulous! He walked my Beagle. My Beagle pulls hard on his leash and has leash aggression when he sees bikes or other dogs. Joe handles hi... (more)"

10. Shani

Outdoorsy pet lover home full time

Skokie, IL, 60076

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

"Shani has a magical way with dogs. They are trustworthy, empathetic, and kind. I have had them take care of my 2 large dogs and house multiple times, and I... (more)"

11. Joy

Reliable Caring Dog Walker

Winnetka, IL, 60093

Drop-In Visits, Dog Walking

About: Describe what the pet's routine would be like in your care: I would arrive at the agreed upon time and safely take your dog on a walk to allow for... (more)

12. Shani

GREAT company/care for your dog!

Winnetka, IL, 60093

Drop-In Visits, Dog Walking

"Shani is wonderful with my dog Ruby who is a 60 lb redbone Coonhound. Ruby is always so excited to see her and Shani is great about leaving me notes and tex... (more)"

Available this weekend
13. Carter

I haven’t met a dog that hates me

Wilmette, IL, 60091

House Sitting, Drop-In Visits, Dog Walking

"Carter is amazing with pets! I’ve had him watch my dog a few times and he always makes sure she is happy and fed. He’s great with making sure that my dog goe... (more)"

Confirmed Memorial day Availability
14. Charles

Passionate and dependable

Northfield, IL, 60093

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: I grew up with a golden retriever named Tess she made me passionate about dogs through her loving silly ways. After she passed away I got a Westie ... (more)

15. Mimi

Full Time Freelancer and Dog Person

Kenilworth, IL, 60043

House Sitting, Drop-In Visits, Dog Walking

"Mimi is fantastic with dogs! She’s very responsible and very much enjoys playing with pups. She is always punctual, helps keep things clean, and is incredibl... (more)"

16. Will

Retired Chicago Police Sergeant

Wilmette, IL, 60091

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

About: I am a retired Chicago Police Sergeant for 31 years. Retired 7 years ago. I worked in various units through out the city. Being retired my times ar... (more)

17. Skylar

I love making dogs feel loved.

Wilmette, IL, 60091

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

"Skylar has grown up and been around a variety of breed and knows how to handle herself well when coming to them. She is high energy and calm when need be to ... (more)"

Available this weekend
18. Hailey

Love dogs- happy to help!

Winnetka, IL, 60093

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

"For a year or so now, Hailey has done a lot of work dogsitting and has never failed to put forth extra special care with all the dogs she comes into contact ... (more)"

19. Carleasia

I’ll be your dog’s best friend

Winnetka, IL, 60093

House Sitting, Drop-In Visits, Dog Walking

"I cannot begin to thank Carleasia enough for all the help that she has provided my wife and I over the years. Frodo is a an old and brittle Mastiff with diet... (more)"

20. BARBARA

Serene pet-friendly condo

Northfield, IL, 60093

Dog Boarding, Drop-In Visits

About: Long-time dog & cat owner would love to take care of your beloved pet. Your pet will be the focus of my attention, there are no other family member... (more)


As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Winnetka pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Winnetka, IL who meets your — and your pet's — needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet — including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.