House Sitting Jackson Park
Find a loving house sitter to watch over your pets and your home.

Over 2 pet parents in Jackson Park have booked house sitting
Jackson Park, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Keisha was amazing! She helped us out when another sitter cancelled. She took amazing care of our 2 dogs while we were away! She was very responsive, sent lots of pictures, and kept us posted the whole weekend! She truly understood and embraced my dog’s personalities! I would highly recommend her and will be using her again in the future!”
“Emily was great at communicating with us the entire stay, and we could tell from all her updates and pictures that our pups loved having her around. Our flight ended up getting delayed because of the blizzard rolling through Wisconsin this past weekend, and Emily was able to help make sure our pups were let out and fed while we figured out how to get back to Milwaukee. I would absolutely recommend Emily to anyone else looking for expert and friendly care for their pups on Rover. Thank you again!”

“Fatima was amazing to work with. I booked her on short notice before the holiday when my original plans fell through. She offered and made it a priority to come do a meet & greet on days notice. I’m always a little nervous when using a new sitter especially when they stay at mine, but my mind was at ease immediately when I met her. I could tell she has a big heart and really cares for animals. She followed all instructions and she went above and beyond spending time with Diesel doing his favorite activities (walks, playing fetch, swimming, etc.). She was incredibly communicative and sent a lot of pictures and videos which was much appreciated. As a former Rover sitter and a frequent user of Rover’s services, I can confidently say that Fatima is one of the best sitters I’ve come across. I will definitely be using her in the future and have already recommended her to others looking for sitters. Thank you Fatima!!!”


“Angela was amazing!!! We had never left our dog with anyone overnight and she helped me feel comfortable and at ease. She sent lots of pics and updates and loved on our guy all weekend. So grateful!”

“Julianna was incredible! She stayed at my house for a week while we were gone to watch Sophia. She kept me updated on everything that was going on and gave her some extra love when she needed it. Sophia doesn’t love being away from us but Julianna made sure she was okay and did everything she could to make sure she was happy! Would definitely recommend her <3”
“Berenice was great!!! She was easy to get in touch with and sent lots of pictures! My puppy was so happy to see her and tuckered out when I saw him indicating that all his physical and mental needs were met during his full day of care. Trustworthy and reliable! Would definitely book again”

“We were very pleased on how well Jenn took care of our fur baby Zoey. Jenn sent us pictures and updates daily. We will definitely book Jenn again for future dog sitting.”

“Our pup Banzo loved having Lynette care for him. She was very communicative, great with our dog and a super respectful house guest. We will definitely want to use her in the future!”

“We had a wonderful experience with Maiah and would absolutely recommend her. Our beagle can be a bit high-maintenance, but Maiah was so great with her. It gave us peace of mind knowing our pup was in trustworthy, kind, and capable hands. Maiah was also an excellent communicator--we received regular updates, photos, and quick responses, which made it easy to relax while we were away. We wouldn’t hesitate to book with her again!”

“Ryan was fantastic! He took great care of our very large dog, who can be reactive at times. I completely trusted him while we were away for a week. We received lots of updates like we asked. He gave our dog medicine without any issues. We came home to a very happy pup and a spotless house. Ryan even got our mail and watered our flowers while we were away, which was super nice. We highly recommend him and already have our next trips booked with him!”

“Ashley was So responsive and Wonderful with my boys! Thankful she was able to watch them in their house!! Will definitely book again if she is willing to watch them!!”

“We came home clean house and my Esther was taught a trick and very disciplined on the leash in backyard. Alexis is so loving and I highly recommend her. She checked in with us throughout our trip. She is the best!”


“Wow! What can I say? Margaret exceeded every expectation I had for Uecker’s care today! As a new puppy mom who’s only had him for three weeks, leaving him with someone for the first time was a little nerve-wracking. But Margaret made me feel completely at ease. She didn’t just watch him—she played with him, loved on him, reinforced the commands we’ve been working on, and treated him like he was her own. The best part? Walking through the door and finding Uecker snuggled up right next to her. My heart absolutely melted. It was obvious he felt safe, loved, and completely comfortable. I truly couldn’t be happier with the care Margaret provided. Book her before I do, because with my busy schedule, I’ll definitely be calling her again! Thank you so much, Margaret. Uecker already adores you, and so do I!”


“Joe was great with our Fifi, he was really a lifesaver! He stayed at our house as our rescue dog can be a little clingy. I received the cutest pictures and was really able to enjoy myself on vacation knowing she was at home!”

“Andrianne was wonderful! She was communicative throughout her time with Tex. Pictures often! She Not only took good care of our precious dog, but Our Home as well! I would highly recommend Adrianne for your pet sitting needs! We will definitely be using her again! Words I would use to describe her: kind, trustworthy,friendly!”

“Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.”
“We love having Emily stay with our dog and cat when we go out of town! She’s so great with them, we never have to worry about a thing. We always come home to happy animals! She’s also very quick to respond to messages. We love Emily!”

“Stepen and Amelie took great care of our 1 year old dog and our home. They took our dog on multiple walks, played with him and made sure he was comfortable. They were great about keeping us up to date with pictures, videos and messages about how our dog was doing. We came home to a detailed list of what our dog did each day, how much he ate, when he used the bathroom and when he slept. We were very impressed and would recommend Stephen and Amelie.”

The median cost per night for house sitting in Jackson Park is $50
Pet parents share their Rover experiences - Jackson Park
Keisha is an absolute wonder sitter! Our little pup was very anxious about us leaving and Keisha was so very kind, patient and loving. She took extra special care to help our pup feel safe, loved and secure. We will always ask Keisha to come watch our pup anytime we leave or even just to hang out for an afternoon. Trust Keisha to be the best care giver!

Sarah is an absolute star - we’re so lucky to have found her on Rover! Our dogs are so happy and comfortable with her, and we know we can rely on her 100%. Consistent photos and updates, and when we get home, the dogs are so chill that it’s like we never left.

Nicole is absolutely phenomenal! She took such great care of our Siberian kitten. Nicole is very professional, communicative, and you can tell how much she loves what she does! The whole time we were gone she sent us updates and photos. We would 110% recommend Nicole!

Ryan was fantastic! He took great care of our very large dog, who can be reactive at times. I completely trusted him while we were away for a week. We received lots of updates like we asked. He gave our dog medicine without any issues. We came home to a very happy pup and a spotless house. Ryan even got our mail and watered our flowers while we were away, which was super nice. We highly recommend him and already have our next trips booked with him!

Scott was FABULOUS with our dog, Rocket! Rocket is a bit picky, but he wholeheartedly loved Scott, too. Scott had wonderful communication--he gave enough so that I felt reassured that Rocket was doing well, but he also let me just relax while on our trip. He made me feel confident that Rocket was in good hands, and that means the world to me. Scott also took in our mail and watered our garden. Thanks for everything, Scott!

Amanda was wonderful. This was the first time we traveled without our puppy and we were a bit apprehensive. However, Amanda eased our concerns. She arrived a few minutes early which signaled a level of reliability that was very welcome. While we were away, Amanda provided regular updates and pictures. As a result, we were able to enjoy our vacation. And our puppy seemed to genuinely enjoy Amanda. We will definitely use Amanda again. We would feel very comfortable leaving our puppy with her.
Paige is an amazing, young woman and was so loving to my pups. We had a hard journey driving from FL to Milwaukee, and I wanted someone to hang with them while catching up with friends. I could not have picked anyone better. Within minutes, my little Elsa was in love with Paige and King had a new girl friend! I searched the night before and thank God, Paige was the answer :) Obviously, highly recommend Paige.

Sonia and Alex did an absolutely excellent job caring for my dog. He is developmentally delayed, requires daily medication, and is incontinent, so his care takes extra attention and patience. Throughout the 6 days he was with them, they communicated promptly and openly about any challenges that came up, and together we were able to make simple adjustments to ensure his stay was comfortable and successful. They sent pictures frequently, which gave me great peace of mind while I was away. From every photo, it was clear that my dog was happy, well cared for, and comfortable in their care. I am incredibly grateful for the compassion, flexibility, and attentiveness Sonia and Alex showed, and I would wholeheartedly recommend them to anyone—especially those with pets who have special needs.

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- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
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