House Sitting in Windsor

Find a loving dog sitter to watch your dog overnight in your home.

Confirmed availability
President's Day
1. Kerri Verified Background Check

Canine Therapy - Nothing Better!!

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

"I would highly recommend Kerri to anyone!! It was our first time leaving our little guy and Kerri provided updates and sent photos to ease our minds! She c... (more)"

2. Tina Verified Background Check

I volunteered in dog rescue.

Windsor, WI, 53598

House Sitting, Drop-In Visits, Dog Walking

"Tina did a great job with my first pet sitting experience. She listened to all pugsley unique personality disorders and handled him appropriately. She seemed... (more)"

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3. Kayla Verified Background Check

I'd love to meet all the animals!

East Bluff, Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

"Kayla was friendly, communicated regularly, and took good care of Pivo while I was gone. I came home to a clean house and a happy dog. Would absolutely recom... (more)"

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4. Amanda Verified Background Check

Love dogs! All of them!

Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

"Amanda has been around dogs all her life. She is very reliable and caring. Amanda loves to walk and play with the dogs . She will even let them sleep with h... (more)"

Confirmed availability
President's Day
5. Brea Verified Enhanced Background Check

Passionate animal lover!

Bluff Acres, Madison, WI, 53704

House Sitting, Drop-In Visits

"If you are looking for an energetic, caring animal lover...then Brea is the one for you. We have had her stay at our house multiple times to watch our dog, ... (more)"

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6. Camille Verified Background CheckRover 101

Cats Cats Cats!! and some dogs

De forest, WI, 53532

House Sitting, Drop-In Visits

"Camille is very caring for your pet and very professional. We couldn’t have for better care for our dog! (more)"

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7. Erika Verified Background CheckRover 101

Experienced Pack Leader/Trainer

Sun Prairie, WI, 53590

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

"Erika took great care of our dog in our own home. She was responsive in scheduling the dates and scheduled a time to come over to meet our dog prior to the ... (more)"

Confirmed availability
This weekend
8. Isabella Verified Background Check

Flexible and Caring Animal Lover

Madison, WI, 53718

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

"Isabella was extremely p (more)"

Confirmed availability
President's Day
9. Aly Verified Background Check

Loving care when you can't be there

Waunakee, WI, 53597

House Sitting, Drop-In Visits, Dog Walking

"I have used Aly as my dog sitter... Aly stayed at my house and cared for my 2 dogs. She is a very caring and responsible dog lover and caregiver. There wa... (more)"

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10. Janet Verified Background Check

NEED A PET SITTER ASAP?

Madison, WI, 53718

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

"Janet was great with our dog. She came prepared to take notes, which we have never had a dog sitter do and showed us how much she cared. She sent us update... (more)"

Confirmed availability
President's Day
11. Kate Verified Background Check

Engaged and flexible caretaker!

Madison, WI, 53718

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

"Kate was absolutely fabulous! My cat and dog were in great hands for the weekend. I was able to enjoy my time away knowing that they were well taken care o... (more)"

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12. Jordan Verified Background Check

Pet Lover & Soon-to-be Grad Student

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

"Jordan stayed with our yellow lab at the house for 3 nights. While we did not communicate with each other during the stay, our dog seemed happy and content w... (more)"

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13. Hailey Verified Background Check

Fun animal lover!

Deforest, WI, 53532

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

"Hailey is an animal lover. She grew up loving and caring for her families dogs. If your animal needs someone to care for them, she can handle it with love an... (more)"

14. Emma Verified Background Check

Long walks and loads of belly rubs

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

"Emma did a great job with Stevie sending plenty of updates and I came home to a happy dog! (more)"

15. Sarah Verified Background CheckRover 101

Wag whisperer

Madison, WI, 53718

House Sitting, Drop-In Visits, Dog Walking

"Sarah came to help us last minute. We were in a lurch and she helped us out by coming over to meet us and dogs late at night right before we left. She was ... (more)"

16. Nathan Verified Enhanced Background Check

Animal science major, loves animals

DeForest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

"We've used Nathan many times in the past to watch our 2 pooches. From our initial meeting, both dogs warmed up to him immediately and loved him. He bonded qu... (more)"

Confirmed availability
This weekend
17. Abby Verified Background Check

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)

18. Wendy Verified Background Check

Home full time walk your dog

Deforest, WI, 53532

House Sitting, Drop-In Visits, Dog Walking

About: I have rescued many dogs and care for all types. Those that are challenged, shy, or abused, I have brought them around with lots of love or space i... (more)

19. Amanda Verified Background Check

You'll wag your tail too!

DeForest, WI, 53532

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

"Amanda is great! She had cared for my dogs twice now. They are older with health needs and she managed them beautifully. She came over to our house twice a d... (more)"

20. Kassel Verified Background Check

College Student Who Loves Dogs

Waunakee, WI, 53597

House Sitting, Drop-In Visits, Dog Walking

"Kassel is bright, polite and intuitive. She had the dogs at ease right away as well as myself. She took direction about the dogs very well. Upon my return th... (more)"


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Windsor house sitting needs. On Rover, it's easy to find a loving dog sitter in Windsor who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Windsor house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Windsor for your dog — people who'll treat him like family.