Pet Sitting & Drop In Visits in Windsor, WI

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. Shannon

Active mom who LOVES dogs

Windsor, WI, 53598

Drop-In Visits, Dog Walking

"Shannon was GREAT!! Olive was happy and well taken care of. And we loved getting the pictures of Olive playing when Shannon was at our house taking care of h... (more)"

Confirmed availability
Thanksgiving
2. Kerri

Canine Therapy - Nothing Better!!

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

"Kerri was amazing with our Bernese mountain dog puppy! She spent extra time with him, cleaned up a mess he made, played with him, sent us multiple pictures a... (more)"

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3. Melissa

Sebastian's love dogs!

Dane County, WI, 53590

Dog Boarding, Drop-In Visits, Dog Walking

"Melissa is awesome!! (more)"

4. Billie

Dog-lover, lover of walks

Sun Prairie, WI, 53590

Dog Boarding, Drop-In Visits, Dog Walking

"Billie was an extraordinary dog companion. She went above and beyond the duties we had agreed on. Both dogs adore her after one visit. Her first visit was my... (more)"

5. Kristen

Love, snuggles, walks for your dog

Sun Prairie, WI, 53590

Drop-In Visits, Dog Walking

"Kristin has excellent experience with dogs. Amazingingly quickly she was making accurate and insightful observations about my dog’ personalities and needs, e... (more)"

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6. Michelle

Large fenced in yard. Active family

Sun Prairie, WI, 53590

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

"We felt very comfortable having Michelle come into our home to take care of our puppy. She sent us multiple pictures and updates while she was there. Our pup... (more)"

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7. Allison

Triple-threat dog caretaker

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

"Allison was very professional at the meet and greet, and knew exactly how to deal with our big dog that can be fence aggressive or worried about meeting stra... (more)"

8. Tina

I volunteered in dog rescue.

Windsor, WI, 53598

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

About: I grew up with animals on a farm and had house pets. I volunteered in dog rescue for many years, house/pet sitted for friends of friends, worked @ ... (more)

9. Anamaria

Catch Dog Training Academy Student

Sherman Village, madison, WI, 53704

Drop-In Visits, Dog Walking

"Ananaria has helped me numerous times with my dogs. I was looking for a reliable, responsible dog sitter and she certainly has lived up to that. Her knowledg... (more)"

10. Mikayla & Lane

Home Full Time - Kids Love Dogs!

DeForest, WI, 53532

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

About: My kids LOVE playing with dogs and have lots of energy! They are around dogs frequently, (Big and Small)! My husband had dogs growing up his whole ... (more)

11. Mary

Best Doggy Aunt Ever

Sun Prairie, WI, 53590

Dog Boarding, Drop-In Visits, Dog Walking

"Mary is one of the best dog caretakers I have ever known. Some even joke that she takes care of her dog, Bruno, better than she does her friends and family! ... (more)"

Confirmed availability
Thanksgiving
12. Olivia

Dog Lover with Years of Experience!

Windsor, WI, 53598

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

"Olivia loved all my pets and they loved her. She fed and exercised them well! She's Dependable and Happy to do it! Love this Girl! (more)"

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13. Jennifer & Eric

Home with Large Fenced Yard

DE FOREST, WI, 53532

Dog Boarding, Drop-In Visits, Dog Walking

"Jennifer is a caring and attentive dog sitter! I don’t ever have to worry when she watches my pup. She’s a natural with them - plays with them, engages them,... (more)"

14. Shireen

Dog lover with a flexible schedule

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

"Shireen is the best dog sitter I have had! She takes such good care of my Gatsby and sends me photos all the time and keeps me in the loop on how he is doing... (more)"

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15. Bea

Walks-Exercises-Treats-Happy Pet.

Sun Prairie, WI, 53590

House Sitting, Drop-In Visits, Dog Walking

"I have had Bea few times in the last couple years I have two dogs. I have had her short period of time to come out let the dogs out and make sure they're OK... (more)"

16. Sanjli

Lots of time to give to your dog!

Sun Prairie, WI, 53590

Drop-In Visits, Dog Walking

"Sanjli took exceptional care of our pet Maltese; she was so loving with her; our Maltese has very long hair and loves to get dirty! Sanjli not only took gre... (more)"

17. Abby

Dog-lover and owner!

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

"Abby is great! Would definitely use her again and recommend her. (more)"

18. Diane

I have a large fenced in yard

Deforest, WI, 53532

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

About: Hello, I love Animals and I have had pets all my life. I currently own two of my own dogs named Arya and Molly. I also have a couple rescue kitt... (more)

19. Katryna

Entrepreneur in the animal industry

Waunakee, WI, 53597

Drop-In Visits, Dog Walking

About: I am self employed so my schedule is pretty flexible. I have had dogs my whole life, have worked at a doggy day care and dog-sat for numerous peopl... (more)

20. Donald

I will treat your pet as my own.

Windsor, WI, 53598

Drop-In Visits, Dog Walking

About: Hello Everyone, My wife and I currently have a Rhodesian Ridgeback named Ares who loves other dogs and their company. I have rescued 3 doberman pi... (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 Windsor 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 Windsor, WI 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.