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. Annie

Large or Small - I Love 'em All!

Evanston, IL, 60201

Drop-In Visits, Dog Walking

3 repeat clients

"We traveled with piece of mind knowing that Annie was taking care of our Cat! She was responsive, timely, and most importantly wonderful to our pet. Cannot t... (more)"

2. Liz

Your Dog is like My Dog in our Home!

glenview, IL, 60025

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

38 repeat clients

"Thanks so much Liz! The dogs are happy and calm :) (more)"

3. Erin

We Love Dogs & New Dog Friends!!

Northbrook, IL, 60062

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

3 repeat clients

"I would highly recommend Erin as a dog sitter. She is very caring and responsible by nature but in addition loves all animals as her own. If you want to ha... (more)"

4. Emily

Infinite love & time for your dog!

Evanston, IL, 60202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Emily did a great job with my dog Memphis! He was happy and worn out when I got back, so she must have gotten some good walks in with him. I'll definitely ke... (more)"

5. Lizz

Freelance Writer and Free Spirit!

Northbrook, IL, 60062

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Lizz is awesome! She is, very obviously, an animal lover. Cuddles, walks, photos and wonderful communication is what you get with Lizz. I felt 100% comfortab... (more)"

Confirmed Holiday Availability
6. Sarah

Wag whisperer

Skokie, IL, 60077

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Sarah made my cat very happy while I was gone for 3 nights. I was very pleased with her sitting skills. Will be a return customer. Thanks! (more)"

Confirmed Holiday Availability
7. Savannah

I've loved dogs my whole life.

Skokie, IL, 60076

Drop-In Visits, Dog Walking

1 repeat client

"Savannah has done 4 visits for us and she's been completely reliable. (more)"

Available this weekend
8. Rinnie

Professional Experience! Flexible

Chicago, IL, 60201

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Rinnie has been helping me look after my 3 month old puppy for 2 weeks now and I cant recommend her enough. She has been very easy to talk to, flexible, and ... (more)"

Confirmed Christmas Availability
9. Nick

Looking for new four-legged friends

Glenview, IL, 60025

House Sitting, Drop-In Visits, Dog Walking

"Nick did drop in visits for the weekend while I was on a short trip. He was great with my two high energy dogs. Would use Nick again! Everything went smoothly. (more)"

10. Chris

Walks, playing, cuddles, & treats

Wilmette, IL, 60091

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

1 repeat client

"Chris had been great with our puppy, Lincoln. He's flexible and available and keeps us updated when anything out of the ordinary happens (like getting Lincol... (more)"

Confirmed Holiday Availability
11. Charles

Passionate and dependable

Northfield, IL, 60093

House Sitting, Drop-In Visits, Dog Walking

1 repeat client
No Reviews Yet

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)

12. Luke

Dog-Loving Northwestern Student

Evanston , IL, 60201

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Luke did a great job with my two large labs! He responded very quickly and has great communication. I will hire Luke again in the future! (more)"

13. Meredith

DOG FRIENDLY HOME WITH FENCED YARD

highland park , IL, 60035

Dog Boarding, Drop-In Visits

6 repeat clients

"If you want to leave your pet with a family that cares, you are in good hands! From the start Meredith and family were so accommodating and helpful for our f... (more)"

14. Aldona

I'm a professional cat sitter!!

Northfield, IL, 60093

Drop-In Visits

"We were delighted with Aldona's care, compassion, and expert professionalism. She came before we left to do a "meet and greet" and she sent us daily updates ... (more)"

15. Jeremiah

I love dogs. They are amazing! =]

Skokie, IL, 60077

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

1 repeat client

"Jeremiah did an amazing job of taking care of my energetic dog. He took him for walks and provided me with updates while I was away. I would definitely recom... (more)"

Confirmed Holiday Availability
16. Julia

A dog enthusiast eager to help!

Glenview, IL, 60025

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I have used Julia several times now and she is the first person I will call to watch my 2 dogs. She is very reliable and has great communication! (more)"

Confirmed Holiday Availability
17. Theresa

Dog, cat, and excercise lover!

Evanston, IL, 60201

Drop-In Visits

"Theresa is super sweet and caring. She remembers every detail about your pets and their needs. I feel very safe letting her visit them, as she has demonstrat... (more)"

18. Gabby

I love every dog I meet!

Kenilworth, IL, 60043

House Sitting, Drop-In Visits, Dog Walking

"Gabby loves, loves, loves animals. She pampers our 2 cats and 2 dogs and treats them like children. She understands their need for attention and is very lo... (more)"

19. Kristin

I'll Play with your dog!

Glenview, IL, 60025

House Sitting, Drop-In Visits, Dog Walking

"Kristen takes care of my Ragdolls Chip and Skie whenever we go out of town. She comes to feed them, clean their litter and she always stays a little longer t... (more)"

20. Carly

Dream Job- "Pro Dog-Sitter"

Northfield, IL, 60093

Dog Boarding, Drop-In Visits, Dog Walking

"Carly loves dogs and loves being around dogs. She lives in a pet friendly building and wishes she could have her own dog, but her weekly work schedule does n... (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.