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

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Top rated Cannon Park dog boarders

“My Best Friend Bosco had a wonderful place to spend Christmas away from home this year. It’s very difficult to find loving people to watch over your pet and totally trust you made the right choice. Maria & Naylbe were guardian angels! I would recommend them for your next trip vacation away. They were awesome, sent us pictures and updates daily. They gave Bosco TLC !!!!!”


“Yolanda took such incredible care of my dogs, Bailey and Jinx. From the updates, to the photos, and just making sure they were comfortable and happy, every detail was perfect. It is clear that Yolanda is the best and goes above and beyond to make each pet feel at home. I had complete peace of mind knowing my dogs were in great hands and will definitely use her services again—highly recommend!”


“Becky was the best caregiver we found in the Milwaukee area for our pups. She is very communicative and gave our dogs the specific care they needed (one gets pretty anxious in new environments). We have hired her for single day care, an overnight, and a week-long trip out of state. She has a large backyard for the dogs to play in and lots of comfortable beds to rest for when they come inside. Most of all, we appreciate her daily pictures and updates. Highly recommend!”


“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!”


“Above and beyond what I could ever have asked for! Michelle took such good care of my pup and gave her so much love and affection. She was understanding and accommodating of my crazy work schedule and delayed flight home. She even gave me a sweet card and printed photos of Charlie. 100000% recommend and Charlie will be spending time with her and Reggie again. Thank you!!”


“Michelle was amazing! Rowan my cat had a blast it almost seemed like she didn’t want to leave!! She sent tons of pictures over the course of the stay and sent plenty of updates! I will 100% be using her in the future.”


“I had an excellent experience with Ashlee. My dog Sinchi was clearly happy and well cared for during my time away. Ashlee was very communicative and sent updates while. I also really appreciated how flexible they were in accommodating my request on such short notice. It's clear she genuinely cares about the animals she looks after. Will definitely book again!”


“They treated Coco like a member of the family. Gave daily updates with pictures. She did not show the typical signs of stress when she was boarded in the past. Highly recommend!”


“Lillian was so great with my Gus. I got lots of videos & photos during his stay to reassure me that my pup was doing well. She took him to dog parks & on a hike & I could tell he was having a blast! Lillian was a great communicator with me and I would definitely book again!”


“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!”



“Dan and Holly were excellent sitters for our dog! After our meet and great we were extremely comfortable leaving Wendy with this kind couple. Dan was very thorough in the questions he asked, and was open to any questions we had. He will also, as much as you'd like, provide pictures and descriptions of your pets stay while you are away. We would highly recommend Dan and will definitely use him again in the future. Thanks Dan!”


“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.”


“Jaq and I absolutely loved having Janice take care of him overnight while I was on vacation for a week! She was attentive to all his needs (he is reactive to other dogs) and provided regular updates and photos. He loved spending time with her - I think it was a vacation for Jaq, as well!”



“Great experience ! Staija took amazing care of our dog Bruno for two weeks. She was reliable, loving, and kept us updated with photos and messages. Bruno was happy and well cared for the entire time. Highly recommend her!”


“Nikki and her family were amazing with my dog Sweet Potato! He was well looked after and Nikki sent me plenty of sweet updates. Sweet Potato came home one happy pup. Would definitely recommend!”


“Super happy with Ellie’s time spent with Stacey and her family! Appreciated the communication and pics throughout our time away, we could sense the love they gave our girl. Will book again!! 🙏🏽”


“My 10 year old yorkie is anxious when she is not with me, usually whimpers and can't settle, but with April and Brad, she was completely calm and content. They gave her 100% attention and affections and I felt good about here stay with them. Thank you April & Brad!”

Loving dog boarding sitters in your neighborhood
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Scott & Ashley S.Star Sitter

“Scott and family were amazing with Cali- so active and kept us up to date! This was her second time staying with them, and I was never worried about her!”


Maria & Nayibe B.Star Sitter

“My Best Friend Bosco had a wonderful place to spend Christmas away from home this year. It’s very difficult to find loving people to watch over your pet and totally trust you made the right choice. Maria & Naylbe were guardian angels! I would recommend them for your next trip vacation away. They were awesome, sent us pictures and updates daily. They gave Bosco TLC !!!!!”


Yolanda W.Star Sitter

“Yolanda took such incredible care of my dogs, Bailey and Jinx. From the updates, to the photos, and just making sure they were comfortable and happy, every detail was perfect. It is clear that Yolanda is the best and goes above and beyond to make each pet feel at home. I had complete peace of mind knowing my dogs were in great hands and will definitely use her services again—highly recommend!”


Rebecca S.Star Sitter

“Becky was the best caregiver we found in the Milwaukee area for our pups. She is very communicative and gave our dogs the specific care they needed (one gets pretty anxious in new environments). We have hired her for single day care, an overnight, and a week-long trip out of state. She has a large backyard for the dogs to play in and lots of comfortable beds to rest for when they come inside. Most of all, we appreciate her daily pictures and updates. Highly recommend!”


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!”


Michelle Y.Star Sitter

“Above and beyond what I could ever have asked for! Michelle took such good care of my pup and gave her so much love and affection. She was understanding and accommodating of my crazy work schedule and delayed flight home. She even gave me a sweet card and printed photos of Charlie. 100000% recommend and Charlie will be spending time with her and Reggie again. Thank you!!”


Michelle G.
Star Sitter


“Michelle was amazing! Rowan my cat had a blast it almost seemed like she didn’t want to leave!! She sent tons of pictures over the course of the stay and sent plenty of updates! I will 100% be using her in the future.”


Ashlee K.

“I had an excellent experience with Ashlee. My dog Sinchi was clearly happy and well cared for during my time away. Ashlee was very communicative and sent updates while. I also really appreciated how flexible they were in accommodating my request on such short notice. It's clear she genuinely cares about the animals she looks after. Will definitely book again!”


Katharine & Michael S.Star Sitter

“They treated Coco like a member of the family. Gave daily updates with pictures. She did not show the typical signs of stress when she was boarded in the past. Highly recommend!”


Mindy W.
Star Sitter


“Mindy did a fabulous job with Takaani. I felt 100% comfortable leaving her with her. Communication was perfectly performed. Great dog walker and person.”


Lillian T.Star Sitter

“Lillian was so great with my Gus. I got lots of videos & photos during his stay to reassure me that my pup was doing well. She took him to dog parks & on a hike & I could tell he was having a blast! Lillian was a great communicator with me and I would definitely book again!”


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!”




Daniel & Holly L.
Star Sitter


“Dan and Holly were excellent sitters for our dog! After our meet and great we were extremely comfortable leaving Wendy with this kind couple. Dan was very thorough in the questions he asked, and was open to any questions we had. He will also, as much as you'd like, provide pictures and descriptions of your pets stay while you are away. We would highly recommend Dan and will definitely use him again in the future. Thanks Dan!”


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.”


Janice G.Star Sitter

“Jaq and I absolutely loved having Janice take care of him overnight while I was on vacation for a week! She was attentive to all his needs (he is reactive to other dogs) and provided regular updates and photos. He loved spending time with her - I think it was a vacation for Jaq, as well!”


Sarah J.Star Sitter

“Sarah is amazing and great with my boy. I love that she updated me on a daily basis and took great care of Hamburger. Definitely recommended and will be using again!”




Stajia W.

“Great experience ! Staija took amazing care of our dog Bruno for two weeks. She was reliable, loving, and kept us updated with photos and messages. Bruno was happy and well cared for the entire time. Highly recommend her!”


Nikki G.Star Sitter

“Nikki and her family were amazing with my dog Sweet Potato! He was well looked after and Nikki sent me plenty of sweet updates. Sweet Potato came home one happy pup. Would definitely recommend!”


Stacey M.Star Sitter

“Super happy with Ellie’s time spent with Stacey and her family! Appreciated the communication and pics throughout our time away, we could sense the love they gave our girl. Will book again!! 🙏🏽”


April & Brad R.Star Sitter

“My 10 year old yorkie is anxious when she is not with me, usually whimpers and can't settle, but with April and Brad, she was completely calm and content. They gave her 100% attention and affections and I felt good about here stay with them. Thank you April & Brad!”
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 Cannon Park.
Rover makes it easy to find Cannon Park 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.
