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

Hillside, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Ashley took absolutely excellent care of our cat while we were out of the country for a week! I knew from the moment she met our cat during our meet and greet that our little girl was going to be in great hands. Throughout the trip, Ashley reached out with check-ins and photos reflecting how well she was being taken care of. She also responded quickly to any messages and went above and beyond watching our place. We (and our cat) look forward to seeing her again in the future!”

“Emily was great at communicating with us the entire stay, and we could tell from all her updates and pictures that our pups loved having her around. Our flight ended up getting delayed because of the blizzard rolling through Wisconsin this past weekend, and Emily was able to help make sure our pups were let out and fed while we figured out how to get back to Milwaukee. I would absolutely recommend Emily to anyone else looking for expert and friendly care for their pups on Rover. Thank you again!”

“I’ve had Melissa watch my pups multiple times now and it makes traveling so much easier. She is very attentive to the dogs needs makes sure to give them the stimulation they need. I will continue booking her for when I’m traveling”

“I am very very protective over my dog who is a pitbull mix. Jenna is amazing. From day one she made it clear she was confident in working with my dog. My dog is like my child and I wouldn't even trust family to watch him. She gained a relationship with him first starting with weekly walks and he warmed up to her. The updates she provided allowed for a worry free trip out of state knowing my dog was in great hands. Couldn't have asked for a better person to trust with my doggos care!”

About: I love all pets, big and small! I’ve pet sat for family and friends (from puppies to tripod cats) over the last few years. I don’t have any pets of my own so I always enjoy meeting new dogs/cats :) I work 9-5 (mon-friday) and typically work from home once a week. I’m available when I wfh, weeknights and weekends! Would love to use some of my free time to take care of your pets. For overnight stays, I’m available to stay at your house. I know every pet has their own personality, routine and quirks - I do my best to stick to what makes them feel comfortable. I’ll follow your care instructions and treat your pet the way I’d want someone to treat my own. Whether that’s a long walk, trip to the park, pup cup or being a house hippo, I’m happy to accommodate.
“We were thrilled when Travis agreed to watch our pup, Opi. Travis came over in advance to meet us and Opi. We knew he was a great match when he immediately greeted Opi and started petting him. Travis is responsive and sent us photos everyday. Opi really seemed to enjoy his time with Travis! Not only did Travis take excellent care of Opi but also our house! We would definitely recommend Travis to anyone needing a pet sitter and we will for sure use Travis again when we travel. We were able to enjoy our time away knowing our house and pup were in the best of hands. Thank you again!”


“Abby did a great job taking care of Levi! She was very kind, communicative, and kept us updated throughout the stay with photos and messages, which we really appreciated. It gave us peace of mind knowing Levi was in good hands.”


“Alena did a great job taking care of my pup! I booked on short notice, and she was extremely gracious and accommodating, and even she made time for a meet and greet prior. She was prompt in responses when I reached out and sent check-in updates and photos as well. I would definitely recommend and will be rebooking if the need arises!”

“Acacia is lovely! She did a great job staying with our frenchie for a weekend, making sure he was fed, walked, and sooo well loved! She is great at sharing updates and helping coordinate all the loving pieces of our travel. Can’t wait for her to come over again in the future!”

“Maiah did a terrific job taking care of my dog. She gave us daily updates and photos, left the house clean and even stayed with my dog so she didn’t get lonely! Amazing!”

“Talor recently stayed at my home and watched my French bulldog while I was on a work trip. She was amazing and sent the cutest pictures and updates on how things were going back home. I would definitely recommend Talor for your housesitting needs. Hazel cannot wait for her to come over again. :)”

About: I have taken care of dogs and cats of all ages and sizes, even dogs that can be leash, collar, and dog aggressive when walking. I am mostly available later in the week and weekends due to being a full time student, but have breaks in between my school days! There is a green area for dogs down the street from me and a quick 15 minute walk towards the lake for more walking paths!
“Carrianne did a wonderful job caring for my dog when I went out of town for a weekend. Penny takes some time to warm up to people and Carrianne was very patient and understanding throughout that process. She followed the care instructions I left and sent daily updates with important information (e.g., walks, eating habits, general behavior) with photos. She also stayed overnight in my apartment and left everything really tidy. I couldn't be happier with the care Penny received and will definitely rebook for future travel plans!”

About: I was a kennel worker for three years through high school and college, taking care of dogs of all shapes and sizes. I have experience with anxious, aggressive and hyperactive dogs. I’ve been taking care of family and neighbors dogs since I was little. In fact, my first job was walking the neighbor’s dog for 5 dollars a week! I’m also a cat dad to two lovely cats, with experience cat sitting for family and friends as well. I’m a part time employee so I’m free to walk or dog/cat sit during the day on weekdays. I have some availability on weekends, but coach baseball so it depends on that schedule. I have experience working with anxious and nervous pets and will create a calm and safe environment when I come to your home. I have no problem crating dogs or administering medication to pets even if anxious/aggressive.
“River did a great job taking care of our two boys while we were out of town. I am really grateful for the piece of mind. Thanks River! I will definitely be in touch again for our next trip.”

“Michaela did a wonderful job taking care of my two cats! With two different diets and varying levels of pickiness, they can be a little difficult to manage when we’re out of town—but she handled it perfectly! And, very communicative with updates provided while we were away. We came home to bird TV playing for our cats, which was such a considerate touch!”

About: Hey there! I'm a full time caterer and part time dog walker. I find both rewarding for different reasons. I'm a resident of Milwaukee for almost 20 years and am most familiar with the East Side and Riverwest I enjoy walking in general but with a doggo= so much better. I'd love to accompany your fluffy pals and furbabies and nuggets. I work on the East Side at Strange Town. I also cater for Ball&Biscuit Catering. I have a pretty flexible schedule. Overnights will be do-able but not preferred because I do miss my cat when I'm away. In addition to Rover coverage, I carry additional insurance for pet-care providers. Your pet's safety, well-being and happiness are of the upmost importance to me. While caring for dogs, I do not wear earphones/headphones and am very cautious of other animals as well as distracted drivers. I have rescued and given forever homes to five kitties and two doggos in my lifetime.
The median cost per night for house sitting in Hillside is $50
Pet parents share their Rover experiences - Hillside
Ray was a wonderful sitter for our senior dog who is going through some health challenges. She spent several hours in our home with Scooby and took excellent care of him. She’s a true dog-lover. Ray was also very flexible with some late changes to our plans, and she was respectful of our home and it’s contents. Thanks, Ray!

This was our first time using Rover and having someone pet sit (outside of family), and it could not have gone better. Jessica provided lots of pictures and updates, made sure the dogs had food and water and gave my senior dog his medication. I would absolutely recommend!

Hannah was absolutely wonderful! She took such amazing care of my pets and my home, and I truly couldn’t have asked for a better experience. The little pet “report cards” were such a thoughtful and personal touch that made me smile! It was clear how much care and attention she gave them. Most importantly, I had complete peace of mind knowing my pets were safe, happy, and in loving hands while I was away. That kind of reassurance is priceless. I would wholeheartedly recommend Hannah to anyone looking for someone they can truly trust with their furry family members! ❤️

This is the second time Keisha has taken care of our dog Frankie at our house and she will absolutely be our go to if she is available the next time we travel. Our house was also in perfect shape after arriving home Exhausted after our trip. Our dog Frankie was perfectly taken care of! Thanks for everything you do Keisha!!!

Mika was so amazing! I knew my dog was in great hands and felt at ease our whole trip. They asked us how many daily updates we wanted and kept us in the loop with what was going on. I never felt the need to reach out to check in, I knew things were going smoothly.

They were oh so flexible and understanding when it came to last minute watching my baby Mr. Bigg. I cannot thank them enough! I got photos and every night I Came home from work they were outside waiting with my baby. Kept me updated communication was amazing. If I’m ever in the area again I’m booking them immediately

Rebecca was great with Oslo! This was my first time traveling since adopting him and she kept me very informed the whole time. She took lots of great pictures and it looked like he was having fun. My apartment was spotless when I returned and Oslo was very calm. Thank you!

Sara and Ethan were excellent. They swooped to the rescue to cover a full week just a few days before we left (a different sitter canceled last minute). Our pup Bailey adored them, but more importantly, we could tell how genuinely they adored him. He was in great spirits when we returned and had been well looked after. They followed all our guidance and were consistent in providing daily updates. Our house was in great shape too, having watched Bailey here. We will be booking them again soon!

Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How to book house sitting

1. Search
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