Pet Sitting & Drop In Visits in Lake 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. Charli

A Dogs Best Friend

Nobel Park, Madison, WI, 53704

Drop-In Visits, Dog Walking

"I have known Charli for 18 years. Charli has remarkable compassion and understanding for dogs and animals. She has owned dogs her whole life and understands... (more)"

7. 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)

Confirmed Memorial day Availability
8. Stephanie

will give: love, exercise & care

Madison, WI, 53704

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

6 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)

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. 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)

12. 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)

13. 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 loved animals her whole life. She has had many pets over the years and they have all received loving care from her. Animals are a passion of hers. ... (more)"

14. Angie

Our pup loves playmates!

Madison, WI, 53718

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

About: We have a very active 1.5 year old yellow lab who loves to play and nothing burns him out like a good play session with another pup! Since we can’t... (more)

Confirmed Memorial day Availability
15. 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)

16. 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
17. Bea

Walks-Exercises-Treats-Happy Pet.

Sun Prairie, WI, 53590

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I have known Bea many years and have seen how she interacts with her pets. She is very patient and loving and has always taken exceptional care of them. Yo... (more)"

Available this weekend
18. Katerina

Patient Dog-Lover Avail. Full-Time

Bluff Acres, Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Katerina was very friendly and accommodating. Stevie liked her instantly and he was happy and well taken care of. (more)"

19. 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)"

Confirmed Memorial day Availability
20. Dawn

Attentive, loving dog sitter/owner

Sun Prairie, WI, 53590

Dog Boarding, Drop-In Visits

4 repeat clients

"We have used Dawn multiple times for sometimes two weeks at a time while we travel. Our Portuguese Water Dog, Maja loves it there and is well exercised. We h... (more)"


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