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.

1. Jennifer

Great with high energy dogs!

Worthington Park, Madison, WI, 53714

Drop-In Visits, Dog Walking

11 repeat clients

"Jennifer sent great pics and updates. She spent quality time with my puppy. He doesn't like rain but she was patient with him and took him out 3 times to m... (more)"

Confirmed Memorial day Availability
2. Camille

Fenced in Backyard.

De forest, WI, 53532

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

5 repeat clients

"Camille is awesome. She is always prompt and very reliable . Our dog, Duke, loves her visits. (more)"

3. Melissa

Sebastian's love dogs!

Dane County, WI, 53590

Dog Boarding, Drop-In Visits, Dog Walking

5 repeat clients

"Two years ago I met Melissa through a friend who recommended her to help me rehome an 8 year old Labrador Retriever who had been retired from a breeding kenn... (more)"

4. Kelsey

Get help with your weekends!

Sun Prairie, WI, 53590

House Sitting, Drop-In Visits, Dog Walking

About: I love dogs! I own a 3 year old pit-bull, Daisy, who I love to pieces. I love to spoil dogs, to make sure they know how loved they are, but also m... (more)

Available this weekend
5. Caroline

Ready to play and care for your pet

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

"Hello, Caroline would come over and walk/play with Penny when we were out late, and couldn't get back in time to let her out. Penny LOVES Caroline, and... (more)"

6. Stephanie

will give: love, exercise & care

Madison, WI, 53704

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

5 repeat clients

About: Hello! I’m Stephanie && am a COMPLETE dog lover. Leaving my dog is always the hardest/most stressful part of taking trips and I want to serve as a ... (more)

Available this weekend
7. Charli

A Dogs Best Friend

Nobel Park, Madison, WI, 53704

Drop-In Visits, Dog Walking

"Charli is great with dogs! She has 2 wonderful dogs of her own that are spoiled with tlc. She's very kind and would treat all dogs as if they were her own ki... (more)"

8. Tina

I volunteered in dog rescue.

Sun Prairie, WI, 53590

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

5 repeat clients

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. Larissa

Animal Loving Student

Berkley Oaks, Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Larissa was wonderful, as always! My little dog Shadow was given love, her supper, and a nice walk.. I knew I didn't have to worry while I was gone (Shadow i... (more)"

10. 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)"

11. Anita L

Home full-time - lots of playtime

DeForest, WI, 53532

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

"Anita has always had dogs in her life both as a child & an adult. They are such a part of her & she enjoys taking them with her wherever she goes. She’s been... (more)"

Confirmed Memorial day Availability
12. Kelsey

Professional Care Provider

Waunakee, WI, 53597

House Sitting, Drop-In Visits, Dog Walking

26 repeat clients

About: I am a reliable individual who will provide quality care to your dog(s). My hope is that by providing care in your home environment, your dog will ... (more)

13. Abby

Dog-lover and owner!

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

About: Hi there! My name is Abby and I am a major dog lover! I have owned a dog (or two) almost my entire life along with volunteering to transport, babys... (more)

Confirmed Memorial day Availability
14. Dawn

Attentive, loving dog sitter/owner

Sun Prairie, WI, 53590

Dog Boarding, Drop-In Visits

4 repeat clients

"Dawn would make a super pet sitter. She has had animals all her life and seems to have a special place in her heart for any animal. Anyone who has Dawn look ... (more)"

15. Kaylee

Experienced caretaker!

Sun Prairie, WI, 53590

House Sitting, Drop-In Visits

About: I love dogs and have owned/taken care of them all my life. I work at a boarding and daycare facility so I have experience and can cater to your fur... (more)

16. Megan

Adaptive to your dog's needs!

Bluff Acres, Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Megan provided excellent care to my two little hounds when I needed to travel for Thanksgiving. She stopped in multiple times throughout the day for walks, p... (more)"

17. Bea

Walks-Exercises-Treats-Happy Pet.

Sun Prairie, WI, 53590

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Bea has been our dog and cat sitter for many years. Not only does she care for our pets, she also takes care of our house when we are on vacation. It's so ni... (more)"

18. Jamie

Flexible hours and I love walks!

Madison, WI, 53716

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

About: Experience: I have been around dogs all my life. I'm what you call a "dog person" and love dogs more than humans sometimes :) I have had family dog... (more)

Available this weekend
19. Emily

I already love your dog!

MORRISONVILLE, WI, 53571

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

1 repeat client

"Emily was great with my fur baby! She's very attentive and listened closely to all of my instructions for my special needs dog, Kuma. She was patient and und... (more)"

20. 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)"


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.