Doggy Day Care in Hillside, Milwaukee
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Top rated Hillside doggy day care sitters

“Caitlin is the best! She is kind, patient and provides the best cuddles to my snuggly boy. He absolutely loves her and it is so apparent how much she loves and cares for dogs. We are lucky to have found her!”


“Lillian is SO amazing! She has watched my 8 month old Berner puppy and he’s so always happy to go over there. She always sends pictures and videos, and each time my pup looks SO happy and comfortable. Totally recommend her to anyone and will most definitely use her in the future. 😊”


“Miranda is the best. She takes such good care of our people-shy dog. She was patient with him and let him warm up to her on his own, and now he loves going to her house...full on butt wiggles when he makes his way over to her. It gives us great piece of mind to know that he’s so well taken care of.”

“Booked at the last minute, she was flexible & friendly Life saver which allowed us to go to the game without worrying about the pups! She’s 5 mins from Fiserv Stadium which worked perfectly - could not have been easier”


“Thank you so much to Kim! Kim was a fantastic dog sitter for our dog Mushi today. She's very friendly and made us feel very comfortable about leaving our lab mix rescue with her while we enjoyed the Milwaukee Zoo. She walked Mushi and also gave us updates as well as pictures. I highly recommend her to watch your dog.”


“This young lady was amazing, very kind and polite. She provided pics of there park trip and I couldn’t be happier with her service!!! Highly recommend”


“I highly recommend Lucas for anyone needing a reliable dog sitter. He kept Milo safe and entertained. I returned to a happy puppy ❤️ thank you again Lucas and Harley!”


“Jim was great with Abby and great with communicating and sending pics! We will definitely call on Jim again!!”


“Luscely was available last minute and didn't make me jump through hoops to dogsit. She was communicative, fair, and my dog was happy. I will absolutely use her again!”


“Marycruz did an amazing job watching my dog for the day! She was super communicative and friendly. Also, she took her for walks and sent lots of pictures/updates which are always appreciated! Would definitely book again :)”


“Miranda took care of my dog like nobody would. She was flexible and patient, and I will absolutely take my dear Galleta with her again. Miranda is super reliable and clearly loves animals. Galleta had lots of fun with her dog, Bandit. Thanks a lot for an amazing daycare experience for my dog!”


About: My experience caring for dogs and cats will allow me to provide the best care for your pet while you can stay worry free at work, out of town, etc. I’m active and love to be out and about, and would love to help provide your pet with more activity time. I make communication with pet owners a priority so that you’re sure of the care being provided. Thanks for considering me and please contact me with any questions! I’m a virtual school psychologist, fully remote, which allows me to have great flexibility throughout the week to be able to care for your pets! I ensure pets are safe and comfortable in my care. I’m attentive to their needs and careful to follow owners’ instructions and guidelines. I’ve been described as reliable, trustworthy, helpful, and tidy.

About: Growing up, I have had animals in my family so I have taken care of animals at a very young age. I also use to work at a doggy daycare during college where I would watch and take care of 70+ dogs per shift! I’m currently unemployed for the next 5 weeks as I make my move from Madison to Milwaukee! I will be living in Milwaukee starting August 5th and will be available all times of the week! Once I start my corporate job in September I will be available on the weekends! I love interacting and being active with dogs, I live in a pet-friendly apartment with a huge area of green space they can walk around in! I also enjoy taking them on walks and making sure they are getting the attention they need!


About: ## INTRODUCTION Howdy there, thanks for choosing my Rover! I go by Billy! First things first — My highest priority is the safety and well-being of any dog in my care. Outside of that, I'm also big on making sure they have a blast, are loved, and feel secure in my home. I am energetic and warm, yet firm. I've owned and raised 4 dogs over the course of 18 years, from puppydom to old age, and have cared for many more. I am adept at handling dogs large and small - physically and training-wise. ## SCHEDULE I am fortunate to have a highly flexible schedule. Your dog will always be safe by my side. I’m quite fond of dogs, so it’s a joy for me to spend my time in this way. ## APPROACH TO CARE I want to understand the needs and expected behaviors of any pet in my care, given your specific guidance and instructions. I am highly communicative and err on the side of caution, as your doggo’s safety and well-being are absolutely the highest priority for me. I have a highly flexible schedule since I'm in the middle of a job search, so I'll have all the time in the world to hang, play with, and co-work with your pup! I have the entire upper floor of my house available for your dog to lounge and roam in, equipped with multiple dog beds and lots of toys. There's also a fenced yard in the back whose concretedness is optimal for ball bouncing and catching, keep away, chasing, and more!

“Chelsea was a great and responsive sitter who provided lots of pupdates. 10/10. Will book again!”


“Marisa was very attentive to my pup during her stay. My dog doesn’t love new environments and gets anxious when separated from me and Marisa gave her her full attention and ensured she felt comfortable during her stay which I greatly appreciated. 10/10 recommend!”



About: Growing up, I never had a moment without a dog (or other animals including a pet pig and multiple snakes) in the family. From owning breeds such as Great Danes, to Golden Doodles, to a Great Pyrenees, my family has luckily passed the dog-loving gene on to me. I recently rescued a senior Chihuahua mix and she has made everyday so fulfilling. I love helping her (and secretly myself lol) make new doggy friends! Combined with my love for the outdoors and exercise, your dog and I are sure to have a great time. Spending time with your dog is not only doing a favor for you, but also for me! My passion for animals is something that I am proud of and would love to continue. I work from home, live in a single family home with a fenced in yard, take frequent walking breaks, and love having company! I also have the flexibility in doing drop in visits, sitting, or other pet care needs. Familiar with pets of all temperaments, learning your pets personality and boundaries is extremely important to me. Whether they like their space in their crate, or need to be cuddled close on the couch, their comfort is my top priority.

About: I don’t own any pets myself, but at least once a month I adopt a dog or cat for the weekend from the shelter, which I love doing so much. I am very patient with any type of animals and love playing with them!! I am pretty flexible with anytime or anywhere. I do not own a car but should be no trouble for me. Just reach out a little in advance and everything with be perfect They are allowed anywhere in my house. And I love going on walks and just exploring. I’d say I have a lot of energy myself so playing till we’re both tired is no problem with me!

“Monica was super nice & communicative, accommodating in the face of a spontaneous (last minute) request for pup-sitting our frenchie, beautiful clean home in a convenient downtown Milwaukee area. So grateful we found her!”

Loving doggy day care in your neighborhood
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Caitlin K.Star Sitter

“Caitlin is the best! She is kind, patient and provides the best cuddles to my snuggly boy. He absolutely loves her and it is so apparent how much she loves and cares for dogs. We are lucky to have found her!”


Lillian T.Star Sitter

“Lillian is SO amazing! She has watched my 8 month old Berner puppy and he’s so always happy to go over there. She always sends pictures and videos, and each time my pup looks SO happy and comfortable. Totally recommend her to anyone and will most definitely use her in the future. 😊”


Miranda O.Star Sitter
“Miranda is the best. She takes such good care of our people-shy dog. She was patient with him and let him warm up to her on his own, and now he loves going to her house...full on butt wiggles when he makes his way over to her. It gives us great piece of mind to know that he’s so well taken care of.”


Adrienne N.Star Sitter

“Booked at the last minute, she was flexible & friendly Life saver which allowed us to go to the game without worrying about the pups! She’s 5 mins from Fiserv Stadium which worked perfectly - could not have been easier”


Kim S.Star Sitter

“Thank you so much to Kim! Kim was a fantastic dog sitter for our dog Mushi today. She's very friendly and made us feel very comfortable about leaving our lab mix rescue with her while we enjoyed the Milwaukee Zoo. She walked Mushi and also gave us updates as well as pictures. I highly recommend her to watch your dog.”


Tishara M.

“This young lady was amazing, very kind and polite. She provided pics of there park trip and I couldn’t be happier with her service!!! Highly recommend”


Lucas Y.Star Sitter

“I highly recommend Lucas for anyone needing a reliable dog sitter. He kept Milo safe and entertained. I returned to a happy puppy ❤️ thank you again Lucas and Harley!”


James H.

“Jim was great with Abby and great with communicating and sending pics! We will definitely call on Jim again!!”


Iuscely F.

“Luscely was available last minute and didn't make me jump through hoops to dogsit. She was communicative, fair, and my dog was happy. I will absolutely use her again!”


Marycruz A.

“Marycruz did an amazing job watching my dog for the day! She was super communicative and friendly. Also, she took her for walks and sent lots of pictures/updates which are always appreciated! Would definitely book again :)”


Miranda E.

“Miranda took care of my dog like nobody would. She was flexible and patient, and I will absolutely take my dear Galleta with her again. Miranda is super reliable and clearly loves animals. Galleta had lots of fun with her dog, Bandit. Thanks a lot for an amazing daycare experience for my dog!”


Morgan S.
“Morgan has such a love for animals! She is so sweet with my pup, Kona. She has sitted for Kona multiple times and I have so much trust in her. Couldn’t have asked for a better pet sitter!”


Naomi M.
“Naomi has been around animals her whole life big and small. Our family currently own two double mastiff and two cats. When she comes home on weekends and holidays, these animals are her first priority by greeting them with hugs and kisses. She is a responsible and loving individual all around and would be perfect for the position of caring for others fur babies.”




William L.
“William took excellent care of my dog while I was out of town for the weekend. She can be highly anxious when I leave her behind, but William was loving and caring and made sure she was well taken care of. Will be using him again in the future.”


Chelsea P.

“Chelsea was a great and responsive sitter who provided lots of pupdates. 10/10. Will book again!”


Marisa C.

“Marisa was very attentive to my pup during her stay. My dog doesn’t love new environments and gets anxious when separated from me and Marisa gave her her full attention and ensured she felt comfortable during her stay which I greatly appreciated. 10/10 recommend!”




Madeline R.
“Madeline has watched my dogs multiple times while I’ve been out of town. My dogs always seem to be happier than when I left. Nothing but positive feedback for this bright young lady.”


Khalil C.
“Khalil has watched my cats countless number of times over the past few years. He always treats them as his own and is attentive to the care he gives. My three cats all have polar opposite personalities and he has learned to attend to them uniquely in their preferred ways. I would recommend him to anyone who has a pet.”


Monica M.


“Monica was super nice & communicative, accommodating in the face of a spontaneous (last minute) request for pup-sitting our frenchie, beautiful clean home in a convenient downtown Milwaukee area. So grateful we found her!”


Mikalanne T.Star Sitter

“Mikalanne is so kind and professional. They took our Cavapoo for the weekend and provided helpful updates and excellent care. Highly recommend.”
Hillside dog parents share their Rover experiences
Took great care of our dog Lula! Sent updates and pictures! 😊 Definitely recommend and will use again!

Luscely was available last minute and didn't make me jump through hoops to dogsit. She was communicative, fair, and my dog was happy. I will absolutely use her again!

This young lady was amazing, very kind and polite. She provided pics of there park trip and I couldn’t be happier with her service!!! Highly recommend

Mikalanne is so kind and professional. They took our Cavapoo for the weekend and provided helpful updates and excellent care. Highly recommend.

Popular requests near you
Select a filter and find qualifying Hillside sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away3. Book & Pay
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Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Doggy Day Care FAQs
Frequently asked questions about Rover
Typically, sitters offering doggy day care on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Hillside.
Hillside doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Hillside sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:
- Puppies and high-energy dogs
- Dogs with special needs, including seniors
- Pet parents who work long hours
- Dogs with separation anxiety
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your doggy day care sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 doggy day care 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 doggy day care service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
