House Sitting in Hillside, Milwaukee
Find a loving house sitter to watch over your pets and your home.

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Loving house sitters in your neighborhood
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1. Megan D.

“Megan was so lovely! She was so great with my (big) dog and I felt really confident leaving my pup with her. She kept me updated the whole time and sent a lot of pics. I came home to my apartment the same way I left it and Megan even left a sweet card. Highly recommend Megan!”




2. Blythe R.

“We can’t say enough good things here. We had a really bad boarding experience and needed to do something different. We were a little hesitant with having someone in our home but Blythe was awesome. We have a large dog who is pretty needy and a little old man. She took pics, gave us updates and did everything we asked and our home looked the exact way we left it. Would highly recommend!”




3. Carole & Shannon C.

“They were amazing with Bodhi - on our return he seemed so happy and well cared for. They also left the house immaculate. We were just very pleased with their care of Bodhi and our house. They are great and we very much appreciate their care.”


4. Amanda C.


“Amanda was great to work with! She was prompt to respond and set up a meet and greet. She had a questionnaire for me to fill out covering all bases about Theo’s care and house sitting which I thought was really helpful! Theo seemed to like her a lot and was quite relaxed when I returned from my trip. I got daily updates with pictures. Would definitely like to work with her again :)”


5. Rachel H.

“Rachel was wonderful! She kept us updated the whole time and our boy was so happy! She took him to the dog park every day and made sure she had a great time while we were gone. We’ll use her every time we can if she’s free!”


6. Melissa H.

“Melissa is a great overnight dogsitter. She followed all the instructions for my dog and bullies have a lot of instructions. Ha! She provided updates everyday and you can tell she enjoys dogsitting. I came back to happy dog.”


7. Jessica Z.

“Jessica Z stayed in my house with my 14 y/o blind Boston Terrier. She was wonderful. I received daily updates and photos, she clearly took excellent care of my pup. She left my place spotless and I would highly recommend her. She is excellent and I will definitely use her again.”


8. Keisha P.

“We had Keisha stay for a 7 day sit for our dog and cat. Keisha was incredible and everything we could have ever wanted in a sitter! She sent us updates at least daily, sometimes more with pictures which is what we requested! I made an error and she was flexible with adding another day to her stay! Could not recommend her enough, we will definitely use her again in the future!!”


9. Casey R.

“Casey is the best! We always feel like they are taking care of our dog (and our home!!) whenever we hire them. Will ABSOLUTELY hire again, thanks Casey!”




10. Jamila M.


“Jamila is absolutely amazing! We were so impressed and thrilled with the attention to detail while housesitting in addition to all the love and affection given to our cats!! Hands down we have found our go to cat sitter! Perfect”




11. Becca S.


“Becca was super nice,sent updates her whole stay with my puppy Abril. I highly recommend her. I will keep using her services. Thanks Becca for being understanding of my puppy with separation anxiety and made her happy until I got home.”


12. Lily S.

“Lily was fantastic with my animals! She got sick while I was gone, poor thing, but worked right through it, even cleaned the carpet when one of my babies threw up. I would definitely trust her with my animals and place and will be using her services in the future!”


13. Emily R.


“Emily was prompt, respectful, and communicative. She sent pictures and updates and my dog seemed very comfortable and calm when I returned. I highly recommend Emily and will happily book her again in the future if I need a dog sitter!”


14. Travis H.


“We met Travis for a meet and greet ahead of time and he was always very attentive, friendly, communicative, and willing to listen. He took great care of our pup for a week and kept our apartment just how it was when we left. We're looking forward to working with him again in the future!”


15. Jackie C.

“Jackie took such great care of Daisy for me while I was out of town for several days. I didn't worry about a thing while I was gone, she sent texts with photos and updates. Everything was fantastic and I will definitely call her again!”


16. Jenna M.

“We couldn’t be happier with Jenna! Our pup has separation anxiety and Jenna navigates that with compassion and care. Highly recommend!”


17. Vilma C.

“Vilma was great, my dog and house were well taken care of by her. Thank you!”




18. Ashley W.

“Ashley was GREAT! I had a last minute trip pop up this weekend and she immediately responded to help me out. She even dropped what she was doing to come meet her that night! She was super responsive while I was away, and Brooklyn is worn out tonight- which I know is because she had so much fun! Thanks again, Ashley!”


19. Rachel M.

“Rachel cat sat for me. She was very easy to work with and took great care of my kitties!”


20. Talor G.

“I came home a very tired lady from a long day and almost 9 days gone. Besides a few misunderstandings that were figured out right away, Talor was an awesome sitter for my Lola. my Lola is 13 years old and I am a worrying mama. Talor took special care of her and I could see how much Lola loved her too! She was awesome with an older dog. Treated her with a lot of gentleness. I came home to a very straightened out clean house. I have not even finished unpacking and it’s 1:42 AM in the morning and I had to quit and just sit down. I loved the pictures that were sent and I would definitely recommend Talor to anyone that needs an awesome sitter and I will definitely keep her on my list when I need one again. I hope she enjoyed her house sitting experience at my home as much as we both enjoyed her 🩷 Thank you very much, Talor. I appreciate how well you took care of my sweet Lola and made her so happy! Of course she has always been easy to love 🩷”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Hillside on Rover as of Jul 2024 was about $45 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jul 2024, there are 917 house sitters in Hillside. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 88% of Hillside house sitters respond in under an hour.
House sitters in Hillside have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Hillside.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Hillside house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
