Pet Sitting & Drop In Visits in Winston, 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. Renee

Home full-time. Love all animals!

Monroe, WI, 53566

House Sitting, Drop-In Visits, Dog Walking

"Exceeds expectations. Well prepared. Followed my instructions to a T. Will work with her for regular visits. (more)"

Confirmed availability
4th of July
2. Leah & Brad

Free Snuggles with Every Service!

Saint Donatus, IA, 52071

Drop-In Visits, Dog Walking

About: My husband and I have both had dogs our whole lives, and plan to keep this a continued pattern for the rest of our lives. We both live, breath and ... (more)

Calendar Recently Updated
3. Kellsey

Dog walking, training and sitting!

Platteville, WI, 53818

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

About: I have owned dogs and cats my whole life along with doing training, grooming, breeding and I have also worked at a vet clinic. I would love to assi... (more)

Confirmed availability
4th of July
4. Jasper

Previous dog bather, dogs are life.

Dubuque, IA, 52001

House Sitting, Drop-In Visits, Dog Walking

About: Hello! My name is Jasper and I am absolutely in love will all dogs. If your dog has some behavioral issues that’s A okay, I’ve dealt with some craz... (more)

5. Lexi

Super flexible schedule!

La Motte, IA, 52054

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

"Very loving and attentive. Has dog sat for me numerous times and my pup loves her. Able to trust her give medicine on time to our older dog. (more)"

6. Nikki

Loves Dogs

Dubuque, IA, 52001

House Sitting, Drop-In Visits, Dog Walking

"I have two dogs, Avery is a one eyed black lab and Mickey is a 130 pound young English mastiff. My dogs are very important to me and bring my family so much ... (more)"

Calendar Recently Updated
7. Kaitlyn

Enrgetic and loving caretaker

Bernard, IA, 52032

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

"I had Kaitlyn watch my dog a month ago!! I would highly recommend her!! My dog loved her and so did we! We will definitely use her in the future! (more)"

Calendar Recently Updated
8. Kaitlyn

Enrgetic and loving caretaker

Bernard, IA, 52032

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

"I had Kaitlyn watch my dog a month ago!! I would highly recommend her!! My dog loved her and so did we! We will definitely use her in the future! (more)"

Confirmed availability
4th of July
9. Jasper

Previous dog bather, dogs are life.

Dubuque, IA, 52001

House Sitting, Drop-In Visits, Dog Walking

About: Hello! My name is Jasper and I am absolutely in love will all dogs. If your dog has some behavioral issues that’s A okay, I’ve dealt with some craz... (more)

10. Nikki

Loves Dogs

Dubuque, IA, 52001

House Sitting, Drop-In Visits, Dog Walking

"Nikki is a wonderful dog sitter. She listens and asks the right questions. She has been able to care for our dogs, cats and chickens with love and concern... (more)"

11. Lexi

Super flexible schedule!

La Motte, IA, 52054

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

"Lexi was great! Very sweet and we felt totally comfortable leaving her at our house while we were gone for the week with our dog. We would use her again and ... (more)"

12. Renee

Home full-time. Love all animals!

Monroe, WI, 53566

House Sitting, Drop-In Visits, Dog Walking

"Renee has owned dogs for as long as I can remember and loved them with every ounce of her being. I cannot think of anyone better to leave my dogs with than R... (more)"

Calendar Recently Updated
13. Kellsey

Dog walking, training and sitting!

Platteville, WI, 53818

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

About: I have owned dogs and cats my whole life along with doing training, grooming, breeding and I have also worked at a vet clinic. I would love to assi... (more)


Rover.com is the simple, savvy way to find and book Winston drop in pet sitting. It's easy to find the perfect pet sitter — many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Winston. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

Card image cap

1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

Card image cap

2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

Card image cap

3) Book & pay

Our platform makes it easy and secure. No cash necessary.

Card image cap

4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.