Pet Sitting & Drop Ins in Hillside, Milwaukee
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check.Learn more about RoverProtect
Loving pet sitters in your neighborhood
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1. Keisha P.

“She is an amazing pet sitter! Very kind and our dog loves her!”


2. Vilma C.

“Vilma is fantastic! Attentive and good to sweet poppy!”


3. Jessica Z.

“Jessica took such good care of my cat. She gave me updates each time and took photos. I am happy to have Jessica care for my cat and would book with her again.”




4. Carole & Shannon C.

“I can’t say it enough! Carole is an absolute dream! Miss Oaklei hurt her leg and she was so sensitive to the issue. She even got so excited when Oaklei was starting to show signs of improvement! She is AMAZING!!”


5. Valerie S.

“Val took great care of my two cats while I was away. She sent tons of pics and even went above and beyond and took trash out! Would definitely book again.”


6. Casey G.


“Casey again goes above and beyond! He was punctual and followed instructions perfectly. We highly recommend Casey to anyone considering pet care.”


7. Ilene G.

“Ilene was great! We have a foster cat in quarantine with an infection and wanted someone to spend time with him while we were out of town. Ilene was able to give him some quality time and attention, he was a happy camper. The updates we got were good and the photos were perfect. Thank you!”


8. Emily R.


“Emily took great care of my three kitties while I was gone. She was wonderful at communicating and following the instructions I left. The litter area is clean and she watered my plants! I highly recommend her for your pet care. A+++”


9. Megan D.

“Megan was awesome and took great care of my cat while I was out of town! Very thorough and sent awesome drop in reports! Would highly recommend!!!”


10. Jenna M.

“Jenna was amazing! She was so patient and kind with our pup with separation anxiety. She was friendly and very communicative. I felt comfortable leaving our sensitive dog with her for an evening while we went out. We would love to have Jenna watch River again!”


11. Jeffery & Tara W.

“Jeff was super friendly and responded very quickly to our last minute request for a drop in/dog sitting while on our stay in Milwaukee. Our dogs enjoyed making him as a new friend! The next time we’re visiting MKE we will be reaching out again!”


12. Alexandra D.


“Alexandra always does a great job with our dogs! She sent frequent updates with pictures and everyone looked happy and healthy. She is especially patient and sweet with our anxious Aussie. Would recommend her to anyone!”




13. Linnea G.


“This was my first time using Rover and boy, did I win the lottery with Linnea! My dogs were happy and the photos she sent warmed my heart. I have complete trust with her. Zero complaints!”


14. Jensen M.
“Jensen has been a great caretaker for my cats while away and for my dog for walking. My pets love him and he is so respectful of our home and learning how each of our pets likes to be interacted with. Our dog is a bit anxious and his experience with similar animals makes our pup feel at ease and allows us to relax knowing all is well.”


15. Valeria J.
“Valeria loves pets and is very excited to adopt a puppy of her own one day. The main reason she wants to work on rover is to spend time with animals. She is very responsible and somebody you can rely on and trust.”


16. Molly S.
“We have two large dogs and Molly is so incredible with them! They are taken on walks, played with and well taken care of when Molly is watching them. Leaving your pets while you are away can be nerve racking but I always am able to relax knowing they are in Molly’s care. I would highly recommend her to anyone looking for care for their pets!”


17. Lily S.

“We felt extremely comfortable and confident having Lily care for Bailey today. Very professional, detailed update, and cute pictures too. We have already booked a multi-nite stay with her in August.”


18. Jackie C.

“Our kitty was in great spirits when we returned. It was evident that she had been well taken care of. Jackie was amenable to our requests and provided helpful and frequent updates. Thank you, Jackie!”


19. Maci P.
“Maci is a loving and caring friend that everyone needs in life. By spending just a minute with her, you'll easily be able to see the kind of person she is. If you want your dog cared for by a genuine and compassionate person (for humans and dogs), hands down she's the best option.”


20. Kane H.
“Hello. I am Kane’s mom and have known Kane his whole life. Kane has always grown up with both cats and dogs. He understands how to walk them feed them care for them and give them love.”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a 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 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 pet 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.
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Hillside on Rover as of Jul 2024 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Jul 2024, there are 280 pet sitters in Hillside. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 85% of Hillside pet sitters respond in under an hour.
Pet sitters in Hillside have an average of 12 years of experience. Pet sitters with repeat customers have an average of 5 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Hillside.
Rover makes it easy to find Hillside pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 280 pet sitters in Hillside on Rover, so you’re sure to find the perfect match for your pet! In Hillside, 100% of pet sitters offer daily exercise, 95% offer medication administration, and 95% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
