Dog Boarding in Hillside, WI
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Hillside dog boarders
“Kristin and Bruce did a great job with my older dog, Madigan. She is sometimes anere xious to be away from home, but she was at ease from the minute we walked in the door. This is the first time in the last six years we did not have someone come in to the home. The pictures showed a relaxed, happy dog and her tail and ears were high when I arrived to pick her up. Dogs know people and she is loyal to "her pack", but our dog loved being a part of Kristin and Bruce's pack. I highly recommend Kristin and Bruce. You will not be disappointed!”
“Edith did a wonderful job taking care of our four-legged family member. She was caring, responsible, and an excellent communicator. We were able to enjoy our time away knowing our pup was in such good hands.”
“Teddy adored his stay with Ruby! She really helped me out in a pinch with her flexibility. we also really love the video updates! Definitely recommend Ruby for your pup!”
“Joan is wonderful! We had to book a last-minute stay because the sitter we booked through Rover canceled the morning of. Joan responded to me quick and was available for us to schedule a meet and greet in the morning to make sure it was overall a good fit. She (and her adorable dogs) were super sweet and welcoming. She sent me videos and pictures throughout Navi's stay and kept me updated. Navi loved Sammy and Emma and was so happy to have some sweet friends to play with! Thank you guys again for giving our sweet girl a comfortable and fun place to stay!”
“Our pup had a great time at Gilian's house! Gillian sent pictures and updates on his day each evening. She was extremely organized and easy to communicate with. She even worked on some training commands with him over his almost week long stay. Our pup came home tired and happy.”
“Ellen took terrific care of our old girl! She went above and beyond helping her get through a few health/diet issues that came up during the stay. Very responsive and helpful updates throughout the stay. Would recommend Ellen to anyone looking to board!”
“Amy was awesome!!! We were so grateful to know that our little dog was in such capable and loving hands while we were on vacation. She was very communicative and provided great updates. We will definitely book with her again!!! Thanks Amy!!! 💕🐾”
“I had a fantastic experience with Michelle and her family caring for Cinnamon! They asked plenty of questions beforehand and made sure I knew there would be other dogs boarding at the same time, which I really appreciated. They sent me lots of update photos and videos, keeping me in the loop, and were so pleasant to work with. I would choose them again to look after my pup!”
“My boy stayed with Duane and Lauren and had a great time. They are so kind and communicative with pupdates throughout their stay. I have already recommended them to friends and will definitely use them again!”
“Kaycee and Robert took great care of my two dogs. They sent lots of updates, and communicated clearly with us. I’d highly recommend them, and will reach out to them when I need someone to watch our dogs again.”
“We love Emily so much! She and her family are like a second home to our dog and we are grateful for how loving and caring she is to him. Highly recommend her for any services!”
“I could not ask for a better care provider for my Maltese Ollie, who has been cared for by only family members until recently! Hope went above and beyond to ensure that Ollie was comfortable while I was away. She invited Ollie and me to her home before committing to caring for Ollie. She was honest in sharing his daily joys and stressors, which was refreshing! She also provided suggestions to improve Ollie's comfort the next time I am away - too awesome!”
“Yoki and Derek were great with Ziggy and Zoey, who were staying overnight away from me for the first time in their lives! They were very patient with my pups and generously shared photos throughout the duration of the dog’s stay.”
“Amanda and her wonderful family take great care of our dog while we are away. We are very happy with the care he receives! We have no worries about our dog while he is at Amanda's. We know he is being well loved while we are gone!”
“5 stars!! ⭐️ 🌟 🌟 💫 ⭐️ Jessica is amazing! She graciously dealt with our uncertain and hetic schedules. She went over and above, driving to my home to pick my dog up. Even when he was initially bashful/scared, she waited and took extra time. Gave him extra love and care, car rides, treats, and nap time together. I felt he was safe, content, and at ease while in Jessica’s home. We will definitely be hiring her again!!”
“Clover had an awesome time with Sarah and her pups. This was our first time using Rover and Sarah made us super comfortable with the process. She was very fast with responses, and sent updates and photos while we were away. Her dogs were very friendly with us and made quick friends with Clover. Would recommend to anyone, and will definitely use again.”
“This was the best experience with a pet sitter we’ve had amongst all of our dogs. We always thought our other sitters were great, and they were/are, but this experience far exceeded our expectations. Our dog Bunny hasn’t had a lot of experience with a sitter other than my mom and another Rover appointment. I was nervous about leaving her somewhere for an overnight, but immediately I learned I had nothing to fear. Bunny fit in like family! We were also treated with kindness and photo updates were sent throughout the stay! Bunny loved her time so much that she didn’t want to leave. Luckily, she only has 20 days to wait until her next visit! Thank you so much!”
“Tanya was amazing. We had tried to find a pet sitter for our very anxious/sometimes aggressive dog Millie for a long time, and finally met Tanya. She clearly is very passionate about helping animals feel safe and cared for, and was so compassionate about our poor dog's fears and problems. We did a trial sleepover before our 10-day trip and it went great. When we were on our trip, Tanya sent us frequent updates and videos, showing how well Millie was doing. She replied quickly to our texts and was very reassuring. When we picked Millie up, she appeared well cared-for and fine (or as fine as our dog gets!) We HIGHLY recommend Tanya!”
Loving dog boarding sitters in your neighborhood
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Kristin & Bruce M.Star Sitter
“Kristin and Bruce did a great job with my older dog, Madigan. She is sometimes anere xious to be away from home, but she was at ease from the minute we walked in the door. This is the first time in the last six years we did not have someone come in to the home. The pictures showed a relaxed, happy dog and her tail and ears were high when I arrived to pick her up. Dogs know people and she is loyal to "her pack", but our dog loved being a part of Kristin and Bruce's pack. I highly recommend Kristin and Bruce. You will not be disappointed!”
Edith S.Star Sitter
“Edith did a wonderful job taking care of our four-legged family member. She was caring, responsible, and an excellent communicator. We were able to enjoy our time away knowing our pup was in such good hands.”
Ruby A.
Star Sitter
“Teddy adored his stay with Ruby! She really helped me out in a pinch with her flexibility. we also really love the video updates! Definitely recommend Ruby for your pup!”
Robert L.Star Sitter
“Robert does a great job taking care of my pup. I appreciate Robert's regular communication. Paisley seems to enjoy spending time with Robert.”
Joan F.Star Sitter
“Joan is wonderful! We had to book a last-minute stay because the sitter we booked through Rover canceled the morning of. Joan responded to me quick and was available for us to schedule a meet and greet in the morning to make sure it was overall a good fit. She (and her adorable dogs) were super sweet and welcoming. She sent me videos and pictures throughout Navi's stay and kept me updated. Navi loved Sammy and Emma and was so happy to have some sweet friends to play with! Thank you guys again for giving our sweet girl a comfortable and fun place to stay!”
Gilian S.Star Sitter
“Our pup had a great time at Gilian's house! Gillian sent pictures and updates on his day each evening. She was extremely organized and easy to communicate with. She even worked on some training commands with him over his almost week long stay. Our pup came home tired and happy.”
Ellen S.Star Sitter
“Ellen took terrific care of our old girl! She went above and beyond helping her get through a few health/diet issues that came up during the stay. Very responsive and helpful updates throughout the stay. Would recommend Ellen to anyone looking to board!”
Amy G.
“Amy was awesome!!! We were so grateful to know that our little dog was in such capable and loving hands while we were on vacation. She was very communicative and provided great updates. We will definitely book with her again!!! Thanks Amy!!! 💕🐾”
Michelle F.
“I had a fantastic experience with Michelle and her family caring for Cinnamon! They asked plenty of questions beforehand and made sure I knew there would be other dogs boarding at the same time, which I really appreciated. They sent me lots of update photos and videos, keeping me in the loop, and were so pleasant to work with. I would choose them again to look after my pup!”
Duane & Lauren S.Star Sitter
“My boy stayed with Duane and Lauren and had a great time. They are so kind and communicative with pupdates throughout their stay. I have already recommended them to friends and will definitely use them again!”
Kaycee & Robert R.
“Kaycee and Robert took great care of my two dogs. They sent lots of updates, and communicated clearly with us. I’d highly recommend them, and will reach out to them when I need someone to watch our dogs again.”
Emily L.
“We love Emily so much! She and her family are like a second home to our dog and we are grateful for how loving and caring she is to him. Highly recommend her for any services!”
Hope R.
“I could not ask for a better care provider for my Maltese Ollie, who has been cared for by only family members until recently! Hope went above and beyond to ensure that Ollie was comfortable while I was away. She invited Ollie and me to her home before committing to caring for Ollie. She was honest in sharing his daily joys and stressors, which was refreshing! She also provided suggestions to improve Ollie's comfort the next time I am away - too awesome!”
Yoki & Derek Z.Star Sitter
“Yoki and Derek were great with Ziggy and Zoey, who were staying overnight away from me for the first time in their lives! They were very patient with my pups and generously shared photos throughout the duration of the dog’s stay.”
Amanda K.Star Sitter
“Amanda and her wonderful family take great care of our dog while we are away. We are very happy with the care he receives! We have no worries about our dog while he is at Amanda's. We know he is being well loved while we are gone!”
Joe H.Star Sitter
“Thanks for another great stay, Joe and Sadie! We can’t recommend y’all enough — always a great experience with a kind and accommodating host. See you next time!”
Jessica P.
“5 stars!! ⭐️ 🌟 🌟 💫 ⭐️ Jessica is amazing! She graciously dealt with our uncertain and hetic schedules. She went over and above, driving to my home to pick my dog up. Even when he was initially bashful/scared, she waited and took extra time. Gave him extra love and care, car rides, treats, and nap time together. I felt he was safe, content, and at ease while in Jessica’s home. We will definitely be hiring her again!!”
Sarah S.
“Clover had an awesome time with Sarah and her pups. This was our first time using Rover and Sarah made us super comfortable with the process. She was very fast with responses, and sent updates and photos while we were away. Her dogs were very friendly with us and made quick friends with Clover. Would recommend to anyone, and will definitely use again.”
Glenda & Nathan & Sandra (Alex) M.Star Sitter
“This was the best experience with a pet sitter we’ve had amongst all of our dogs. We always thought our other sitters were great, and they were/are, but this experience far exceeded our expectations. Our dog Bunny hasn’t had a lot of experience with a sitter other than my mom and another Rover appointment. I was nervous about leaving her somewhere for an overnight, but immediately I learned I had nothing to fear. Bunny fit in like family! We were also treated with kindness and photo updates were sent throughout the stay! Bunny loved her time so much that she didn’t want to leave. Luckily, she only has 20 days to wait until her next visit! Thank you so much!”
Tanya K.
“Tanya was amazing. We had tried to find a pet sitter for our very anxious/sometimes aggressive dog Millie for a long time, and finally met Tanya. She clearly is very passionate about helping animals feel safe and cared for, and was so compassionate about our poor dog's fears and problems. We did a trial sleepover before our 10-day trip and it went great. When we were on our trip, Tanya sent us frequent updates and videos, showing how well Millie was doing. She replied quickly to our texts and was very reassuring. When we picked Millie up, she appeared well cared-for and fine (or as fine as our dog gets!) We HIGHLY recommend Tanya!”
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 dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. 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?
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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 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
As of Aug 2025, 370 sitters provided dog boarding in Hillside. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 92% of Hillside dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Hillside have an average of 18 years of experience. Dog boarding sitters with repeat customers have an average of 10 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters 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
There are 370 dog boarding sitters in Hillside on Rover, so you’re sure to find the perfect match for your dog! In Hillside, 94% of sitters offer daily exercise, 94% offer medication administration, and 94% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
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.
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