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Pet Sitting & Drop In Visits in Winslow, 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. Andrea

Huge animal lover

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Andrea takes such good care of our Wrigley!! She is very detailed and a fantastic communicator!! (more)"

2. Rae

friends call me 'Dog whisperer'

McFarland, WI, 53558

House Sitting, Drop-In Visits, Dog Walking

"Rae is extremely responsible, respectful and passionate about all animals and I even trust her with my child. She’s reliable and straight up wonderful person (more)"

3. Renee

Home full-time. Love all animals!

Monroe, WI, 53566

House Sitting, Drop-In Visits, Dog Walking

"Renee has been making drop-in visits for our 12-yr-old dog for six months. Since she started watching Max, he was diagnosed with Lyme disease. She has made v... (more)"

4. Brianna

Animal lover

monroe, WI, 53566

House Sitting, Drop-In Visits, Dog Walking

"Brianna is an amazingly sweet, kind and generous person, and this is not just with humans, but with animals as well. The way she cares for and helps animals ... (more)"

5. 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)

6. Willa

Dog-Loving College Student

Capitol, Madison, WI, 53703

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

About: I've always been passionate about dogs and people. As a social welfare major at UW-Madison, the patience, empathy, and compassion that I apply to m... (more)

7. Susanne

I love pets and they love me!

Monticello, WI, 53570

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

About: I have been a happy dog owner for over 30 years. At several times have had more then 3 dogs and several cats in my home with no issues. I work from... (more)

8. Jess

Confident, reliable and resourceful

Schenk-Atwood, Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

"Jess is a loving, caring, and incredibly responsible dog sitter. Our dog loves when Jess is around to take care of him. She showers him with attention, and o... (more)"

9. Michelle

A walk in the park for your pups!

Rockton, IL, 61072

Drop-In Visits, Dog Walking

"Michelle understands that our dogs are family. We think of Michelle first when we are going to be out of town and need a sitter. It’s so reassuring to us to ... (more)"

10. Rachel

Outgoing, caring, pet lover

Monticello, WI, 53570

Drop-In Visits, Dog Walking

About: I've grown up with dogs my whole life and have had experience with so many different breeds. As a child we used to show dogs and some of my family ... (more)

11. Courtney

Dog lover of all breeds shapes size

Loves Park, IL, 61111

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

About: I have had anywhere from a yorkie to two giant Rottweillers. My oldest Rottweiller is a trained service animal that I performed training myself. I ... (more)

Confirmed 4th of July Availability
12. Trenton

Dogs are my best friends.

Beloit, WI, 53511

House Sitting, Drop-In Visits, Dog Walking

"Trenton, took care of my border collies, Doc and Ace many times. He walked them and fed them. I trust him with my dogs and look forward to him dog sitting in... (more)"

13. Robert

Good person with a good heart

Brodhead, WI, 53520

House Sitting, Drop-In Visits, Dog Walking

"I have known Bob for most of my life and have always known him to be a gentle and caring person! He's great with animals and loves cats. I would most definit... (more)"

The next time you head out of town and need someone to take care of your pets — and check in on you home — turn to Rover. It's easy to find a loving Winslow pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Winslow, IL, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). 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 house and pet sitter all through Rover — it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Winslow pet sitters and avoid the kennel.

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

How it works

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1) Browse Sitters

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

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2) Contact Sitters

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

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3) Book & pay

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

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4) Enjoy your trip

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