Doggy Day Care in Hillside, Milwaukee, WI
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

“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. 😊”


“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.”


“Adrienne was Roo’s best friend for a day, and was everything I was looking for and more. Roo had a day full of adventures, and Adrienne sent us plenty of photos! We will definitely be return customers. Highly recommended!!”


“This was our first time using rover and any kind of daycare for our dog and Miranda was nothing but amazing! She kept me updated and sent pictures. We will definitely be using Miranda again in the future!”


“Naomi is great. I took a chance given she is new on Rover as she just moved to Milw. she was accommodating to set up a meet and greet a couple days before I needed day care for my pup. what is attentive and listened about my dog. Communicated and sent pictures throughout his day with her. My pup was well cared for and really liked her! sometimes it’s hard when there’s not a lot of reviews, but I am glad I took a chance and I highly recommend Naomi! THANK YOU NAOMI!”


“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!”


“Marycruz is amazing! My dog loves her and gets along great with her pup. She sent lots of pics and was great at communicating. This is the second time she’s watched my dog for day care and she’s very trustworthy! Very glad she’s on Rover - 11/10 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!”


About: I've had dogs since I was a kid, for as long as I can remember. I've had dogs of all breeds, sizes, and personalities. My last dog was trained so well that friends and neighbors decided to get a dog for themselves after meeting him. Currently I have a 3 year old dog at home, along with my wife and 2 teenagers. We all love dogs because of the mutual unconditional love. I love taking dogs on walks, playing fetch with them in our small backyard and going to the dog park is a favorite activity for the whole family. Our dog is happiest when playing with other dogs and then getting so tired she can poop out on our couch while cuddling one of us. We have a small backyard but live in a very dog friendly neighborhood with sidewalks so when playing in the backyard isn't exercise enough long walks are great. I am familiar with giving dogs different medications and dealing with different dog personalities. I am an educator, so I am home for the summer, so our routine is flexible. I typically start the day with a morning walk by 7:00 am and then see where the day takes us. We take our last potty break around 10:00 pm before heading to bed. I have a fenced in backyard. I allow pets on our furniture. I do not have a crate, but I am comfortable crating dogs if that is what they are accustomed to. I have a dog and a cat at home. The cat mostly avoids dogs. I love dogs and they will be safe, loved, and taken good care of. There is usually always somebody at home to watch the pets, and we have a flexible schedule to accommodate to that.


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!

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: 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!

“Josie had so much fun with Monica! I really appreciated Monica's communication: she was quick to respond and she sent plenty of pictures. Highly recommended and will definitely be contacting her in the future!”

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

“Caitlin is wonderful with Mira! I am totally at ease when Mira is with her, and I am also happy for Mira to have such a fun and caring friend…:) 🐶🙋♀️🫶”


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. 😊”


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.”


Adrienne N.Star Sitter

“Adrienne was Roo’s best friend for a day, and was everything I was looking for and more. Roo had a day full of adventures, and Adrienne sent us plenty of photos! We will definitely be return customers. Highly recommended!!”


Miranda O.Star Sitter

“This was our first time using rover and any kind of daycare for our dog and Miranda was nothing but amazing! She kept me updated and sent pictures. We will definitely be using Miranda again in the future!”


Naomi M.

“Naomi is great. I took a chance given she is new on Rover as she just moved to Milw. she was accommodating to set up a meet and greet a couple days before I needed day care for my pup. what is attentive and listened about my dog. Communicated and sent pictures throughout his day with her. My pup was well cared for and really liked her! sometimes it’s hard when there’s not a lot of reviews, but I am glad I took a chance and I highly recommend Naomi! THANK YOU NAOMI!”


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!”


Marycruz A.

“Marycruz is amazing! My dog loves her and gets along great with her pup. She sent lots of pics and was great at communicating. This is the second time she’s watched my dog for day care and she’s very trustworthy! Very glad she’s on Rover - 11/10 sitter!”


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!”


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!”


Amy T.

“Great dog sitter!”


Keith O.
“Keith is an excellent choice to take care of your furry loved one. Keith is professional, prompt, and clearly has a genuine love of animals. Animals seem to respond very positively to Keith and we feel very confident that our pet is getting the best care when he is with Keith!”




William L.
“William took care of my parent's dog when we went on weekend trip. He sent daily photos and left the house in great condition. Very friend and professional. Would highly recommend and will definitely book again!”


Chelsea P.

“Chelsea is wonderful and very communicative. Would 100% bring my husky to her again”


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.”


Marisa C.

“Super great job watching my dog! Oakley seemed really happy to see her and I loved all the pictures! I definitely would recommend and rebook.”


Morgan S.
“I have two large, active huskies that require a lot of attention. They are fun loving and Morgan was able to provide them with all the love in the world! I can tell Morgan is a very genuine person who truly loves hanging out with pets. She is responsible and will treat your dogs like they are her own. I highly recommend her!”


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.


“Josie had so much fun with Monica! I really appreciated Monica's communication: she was quick to respond and she sent plenty of pictures. Highly recommended and will definitely be contacting her in the future!”
Hillside dog parents share their Rover experiences
Naomi is great. I took a chance given she is new on Rover as she just moved to Milw. she was accommodating to set up a meet and greet a couple days before I needed day care for my pup. what is attentive and listened about my dog. Communicated and sent pictures throughout his day with her. My pup was well cared for and really liked her! sometimes it’s hard when there’s not a lot of reviews, but I am glad I took a chance and I highly recommend Naomi! THANK YOU NAOMI!

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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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.
