Pet Sitting & Drop In Visits in Winchester, IL

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

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1. Maleri

Must love dogs ✅

Jerseyville, IL, 62052

House Sitting, Drop-In Visits, Dog Walking

"This was a wonderful experience for Toby and myself. Maleri took great care of Toby. He seemed very happy when we came home. (more)"

2. Tyler

Around dogs my whole life

Jacksonville, IL, 62650

House Sitting, Drop-In Visits, Dog Walking

"Tyler is excellent with animals. He’s calm and patient with them, and is firm when he needs to be. My lab mix, who usually doesn’t like strangers, warmed rig... (more)"

3. Taylor

Very experienced with puppies!

Carrollton, IL, 62016

House Sitting, Drop-In Visits, Dog Walking

"They take animal care very seriously. If an animal is going through a tough time, they will everything in their power to help or at least make the animal mor... (more)"

4. Natalie

Young, energetic & home full time!

Jacksonville, FL, 32205

House Sitting, Drop-In Visits, Dog Walking

About: I am the biggest dog lover you will ever meet ❤️ My nova is my baby and I will treat yours just the same! We go on lots of walks and play everyday.... (more)

Confirmed availability
This weekend
5. Kendi

Large yard for playing outside!

Jacksonville, IL, 62650

Dog Boarding, Drop-In Visits, Dog Walking

"Kendra has taken care of my dog many times and has always been a good companion for her when I’m away and keeps my dog on the diet that I plan . It’s reassur... (more)"

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6. Maleri

Must love dogs ✅

Jerseyville, IL, 62052

House Sitting, Drop-In Visits, Dog Walking

"Maleri did an amazing job watching our sweet Golden’s while we were away. She gave them much love, attention, and snuggles! The pups are looking froward to ... (more)"

7. Tyler

Around dogs my whole life

Jacksonville, IL, 62650

House Sitting, Drop-In Visits, Dog Walking

"Tyler is excellent with animals. He’s calm and patient with them, and is firm when he needs to be. My lab mix, who usually doesn’t like strangers, warmed rig... (more)"

8. Taylor

Very experienced with puppies!

Carrollton, IL, 62016

House Sitting, Drop-In Visits, Dog Walking

"Was professional and caring for my dogs. Could easily adapt to a farm and great at improvising when needed. So glad I had her. She is well versed in the care... (more)"

9. Natalie

Young, energetic & home full time!

Jacksonville, FL, 32205

House Sitting, Drop-In Visits, Dog Walking

About: I am the biggest dog lover you will ever meet ❤️ My nova is my baby and I will treat yours just the same! We go on lots of walks and play everyday.... (more)


Rover.com is the simple, savvy way to find and book Winchester 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 Winchester. 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.