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.

1. Stephanie

Open availability

HAMBURG, IL, 62045

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

"Stephanie has stayed with my animals numerous times in the last few years. We have dogs, cats, guinea pigs, and hamsters. She does great work! (more)"

2. 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)"

3. 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)

4. Peter

Expert in Animals of All Sizes

Cantrall, IL, 62625

House Sitting, Drop-In Visits, Dog Walking

"I have known Peter literally his whole life and have yet to find an animal he didn't like or a pet he didn't take excellent care of. He quickly learns their ... (more)"

5. Melissa

Large fenced yard, previous vet tec

Jerseyville, IL, 62052

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

About: I have breed, shown, trained and judged dogs all of my life. Previously worked for a veterinarian. I can provide boarding/training and grooming t... (more)

6. Cassi

Will exercise/play & groom your dog

Jacksonville, IL, 62650

Drop-In Visits, Dog Walking

"Cassi has the biggest heart and love for animals, and goes above and beyond to make sure they’re treated the very best! I always know my animals are in good ... (more)"

7. 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)"

8. 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)"

9. Stephanie

Open availability

HAMBURG, IL, 62045

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

"Stephanie has stayed with my animals numerous times in the last few years. We have dogs, cats, guinea pigs, and hamsters. She does great work! (more)"

10. Melissa

Large fenced yard, previous vet tec

Jerseyville, IL, 62052

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

About: I have breed, shown, trained and judged dogs all of my life. Previously worked for a veterinarian. I can provide boarding/training and grooming t... (more)

11. 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)

12. Peter

Expert in Animals of All Sizes

Cantrall, IL, 62625

House Sitting, Drop-In Visits, Dog Walking

"Very nice, polite and good with Teagan! (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.