Dog Boarding in Hillside, Milwaukee, WI
Find a loving dog sitter to watch your dog overnight at your sitter's home.

More resources
A focus on safety
Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check. Learn more about RoverProtect
Top rated Hillside dog boarders

“They took great care of our dog and were very communicative. Love that they only watch little dogs, so we didn't have to worry about a larger dog being too rough. They're super sweet people”


“Yolanda and her family are precious! we received around the clock updates and pictures. My dog was immediately in love with them. They offered lots of play time, treats, and even a new toy. we felt very comfortable and confident in their care, and will def use them again!”


“Michelle was absolutely wonderful! She sent me regular updates, was very attentive to my puppies needs and was overall very kind. I would definitely let her watch my pup again!”


“Kathy and Brad are the best! Kept in great communication while we were gone; we could tell Benjamin settled right in. We are so happy to have a new home away from home!”


“Katharine and Michael were able to help me out in an emergencies situation and were so wonderful to work with. Gus was well cared for and came home happy and content. I will absolutely work with them again in the future.”


“Rebecca & her family are the best with my pup! He gets to be on vacation when I’m on vacation. I love getting updates - he is hanging out with the other pups, playing outside, or snuggly & resting in every one!”


“I needed last minute boarding and Ashley was eager to help. She was a great communicator and took great care of Duncan. I definitely recommend boarding with Ashley.”


“Michelle was wonderful! She took care of our two younger dogs. Provided updates throughout the day and gave our boys plenty of love! Great communication, and plenty of excessive given. I would definitely ask Michelle to sit for us again! Thank you Michelle!”



“Dan and Holly were just awesome! My Toby has a wonderful time vacationing with them and their bassetts. You can tell they are extremely passionate dog lovers and genuinely enjoy and love every dog that comes into their home. We will definitely be booking again!”


“Was very accommodating with a same day request! Thank you, Rhonda! It was very much appreciated, so I could spend some time with my family after recently arriving in town.”


“Lillian was wonderful and attentive to my dog. She sent videos and messages often to keep me updated on their adventures. Would love to book her again in the future!”


“They did a great job with Cooper he loved them and he loved the way he had. Even though he is just a puppy when we locked him up he was pooped out from his walks and was calm and relaxed the rest of the night I would definitely have them watch Cooper again”


“Kim did such a wonderful job caring for my pup, even when he was a bit hard to handle right away. She was communicative and transparent and worked hard to make sure that he was active, comfortable, and well-loved. I wouldn’t hesitate to recommend her services.”


“This was my first time using Rover and I couldn’t be happier with Dawn and her husband! They were so welcoming at our Meet and Greet and made us feel very comfortable leaving Zeke overnight. She sent us updates and pictures of him having a blast in their back yard, so I could tell Zeke was having a great time. I highly recommend Dawn and will definitely be booking with her again in the future!”


“We couldn't be happier with Sarah! Her and her family were incredibly reliable, warm & welcoming, and went above and beyond to ensure Moose was comfortable and well-cared for. When our flight was changed last minute, Sarah was understanding and flexible. We appreciated the daily updates and so many amazing photos. It was so reassuring to see how happy Moose was during his stay. We highly recommend Sarah to anyone looking for a trustworthy and caring dog sitter! We will absolutely be rebooking for our next vacation.”


“Alberto and Chance took good care of our dog while we were on vacation. Meet and greet: Had some scheduling issues but went well once scheduled. Listened to recommendations as our dog can be a difficult greeter, and it went excellently. Intake: Asked lots of good thoughtful questions, somethings I hadn't even thought about. Finn was left in good hands. Stay: Sent lots of pictures and complimented our dogs behavior, and reassured us he was doing well while we were away. Pick-up: I think there were some communication challenges that occurred due to unexpected circumstances so I cannot reasonably deduct a star for that. However if we had a firm pickup this may have created some challenges. I imagine this was a fluke but wanted to share incase it becomes a trending issue. Overall went well and will consider re-booking in the future if it works.”



“MJ is truly a dogowner's kind of sitter. Extremely well attuned to a dog's needs & feelings, whenever I drop off my Abby girl, I know she is staying with someone who actually cares and likes to be around dogs. I've had Abby stay with him several times and MJ is always extremely easy to work with, genuinely affectionate to my dog and responds to bookings ASAP. Plus his house is great for a dog to hang out and explore and he is right next to McLaren Park- which is any dogs dream! Very happy I came across MJ in my Rovering.”


“Lisa took great care of my dog while I was away for about a week! She sent lots of cute and cozy pictures of him hanging out with her animals and was always easy to get in touch with. She also did a good job handling his food aggression and making adjustments to make things work for everyone. I’d definitely recommend her!”

Loving dog boarding sitters in your neighborhood
Search Results


Maria & Nayibe B.Star Sitter

“They took great care of our dog and were very communicative. Love that they only watch little dogs, so we didn't have to worry about a larger dog being too rough. They're super sweet people”


Yolanda W.Star Sitter

“Yolanda and her family are precious! we received around the clock updates and pictures. My dog was immediately in love with them. They offered lots of play time, treats, and even a new toy. we felt very comfortable and confident in their care, and will def use them again!”


Michelle G.
Star Sitter


“Michelle was absolutely wonderful! She sent me regular updates, was very attentive to my puppies needs and was overall very kind. I would definitely let her watch my pup again!”


Kathy & Brad K.

“Kathy and Brad are the best! Kept in great communication while we were gone; we could tell Benjamin settled right in. We are so happy to have a new home away from home!”


Katharine & Michael S.Star Sitter

“Katharine and Michael were able to help me out in an emergencies situation and were so wonderful to work with. Gus was well cared for and came home happy and content. I will absolutely work with them again in the future.”


Rebecca S.Star Sitter

“Rebecca & her family are the best with my pup! He gets to be on vacation when I’m on vacation. I love getting updates - he is hanging out with the other pups, playing outside, or snuggly & resting in every one!”


Ashlee K.

“I needed last minute boarding and Ashley was eager to help. She was a great communicator and took great care of Duncan. I definitely recommend boarding with Ashley.”


Michelle Y.Star Sitter

“Michelle was wonderful! She took care of our two younger dogs. Provided updates throughout the day and gave our boys plenty of love! Great communication, and plenty of excessive given. I would definitely ask Michelle to sit for us again! Thank you Michelle!”




Daniel & Holly L.
Star Sitter


“Dan and Holly were just awesome! My Toby has a wonderful time vacationing with them and their bassetts. You can tell they are extremely passionate dog lovers and genuinely enjoy and love every dog that comes into their home. We will definitely be booking again!”


Rhonda G.Star Sitter

“Was very accommodating with a same day request! Thank you, Rhonda! It was very much appreciated, so I could spend some time with my family after recently arriving in town.”


Karen D.

“The best rover user we’ve had the pleasure of meeting. Plenty of walks, photos, and updates throughout. We will certainly be using Karen again.”


Lillian T.Star Sitter

“Lillian was wonderful and attentive to my dog. She sent videos and messages often to keep me updated on their adventures. Would love to book her again in the future!”


Megan & Richard S.
Star Sitter


“They did a great job with Cooper he loved them and he loved the way he had. Even though he is just a puppy when we locked him up he was pooped out from his walks and was calm and relaxed the rest of the night I would definitely have them watch Cooper again”


Kim S.Star Sitter

“Kim did such a wonderful job caring for my pup, even when he was a bit hard to handle right away. She was communicative and transparent and worked hard to make sure that he was active, comfortable, and well-loved. I wouldn’t hesitate to recommend her services.”


dawn s.
Star Sitter


“This was my first time using Rover and I couldn’t be happier with Dawn and her husband! They were so welcoming at our Meet and Greet and made us feel very comfortable leaving Zeke overnight. She sent us updates and pictures of him having a blast in their back yard, so I could tell Zeke was having a great time. I highly recommend Dawn and will definitely be booking with her again in the future!”


Sarah K.

“We couldn't be happier with Sarah! Her and her family were incredibly reliable, warm & welcoming, and went above and beyond to ensure Moose was comfortable and well-cared for. When our flight was changed last minute, Sarah was understanding and flexible. We appreciated the daily updates and so many amazing photos. It was so reassuring to see how happy Moose was during his stay. We highly recommend Sarah to anyone looking for a trustworthy and caring dog sitter! We will absolutely be rebooking for our next vacation.”


Alberto V.


“Alberto and Chance took good care of our dog while we were on vacation. Meet and greet: Had some scheduling issues but went well once scheduled. Listened to recommendations as our dog can be a difficult greeter, and it went excellently. Intake: Asked lots of good thoughtful questions, somethings I hadn't even thought about. Finn was left in good hands. Stay: Sent lots of pictures and complimented our dogs behavior, and reassured us he was doing well while we were away. Pick-up: I think there were some communication challenges that occurred due to unexpected circumstances so I cannot reasonably deduct a star for that. However if we had a firm pickup this may have created some challenges. I imagine this was a fluke but wanted to share incase it becomes a trending issue. Overall went well and will consider re-booking in the future if it works.”




Michael J K.Star Sitter

“MJ is truly a dogowner's kind of sitter. Extremely well attuned to a dog's needs & feelings, whenever I drop off my Abby girl, I know she is staying with someone who actually cares and likes to be around dogs. I've had Abby stay with him several times and MJ is always extremely easy to work with, genuinely affectionate to my dog and responds to bookings ASAP. Plus his house is great for a dog to hang out and explore and he is right next to McLaren Park- which is any dogs dream! Very happy I came across MJ in my Rovering.”


Lisa W.Star Sitter

“Lisa took great care of my dog while I was away for about a week! She sent lots of cute and cozy pictures of him hanging out with her animals and was always easy to get in touch with. She also did a good job handling his food aggression and making adjustments to make things work for everyone. I’d definitely recommend her!”


Tekoya C.

“Tekoya did an excellent job watching our dog while we were on vacation. Communication was great and he was so easy to work with, I highly recommend Tekoya!”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
Typically, dog boarding sitters 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.
Rover makes it easy to find Hillside dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding 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 dog boarding 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
