House Sitting Hillside

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Hillside, 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.

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Sitter Profile Image: Laurie P.
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Laurie P.
Star Sitter
from
$75
per night
5.0 out of 5 stars
120 reviews
49 repeat clients
36 years of experience
Historic Third Ward, Milwaukee, WI, 53202

This is our second time using Laurie and she is fabulous. She shows up on time, keeps the dogs on their schedule, sends lots of updates, is very attentive to their needs, and the house is always super clean when we get back. I hate leaving my dogs and typically worry about them while away, but with Laurie I don't worry at all. We've already got her scheduled again next month!

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Kasey M.
Sitter Profile Image: Megan D.
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Megan D.
Star Sitter
from
$85
per night
5.0 out of 5 stars
64 reviews
15 repeat clients
11 years of experience
Milwaukee, WI, 53204

Megan was so great! We got lots of pics and videos and our pups were happy and chill when we got back, even after it being too cold to go outside much. Will definitely call again - thanks!

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Carley M.
Sitter Profile Image: Acacia L.
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Acacia L.
Star Sitter
from
$40
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
8 years of experience
Milwaukee, WI, 53212

The best Rover sitter I have had. Communicative, clean, great with Gertie, and an all around kind, responsible, and trustworthy person. Thank you Acacia! It means the world to me 🥰

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Naomi S.
Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$90
per night
5.0 out of 5 stars
153 reviews
57 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Jackie was great. This was our first time having someone come to our house to watch our (almost) 11 year old chocolate lab. He can be finicky and has pretty strong anxiety, but Jackie was great with updates, and when we came home, Otis seemed in great shape...much better than taking him somewhere else. Would highly recommend Jackie, especially to anyone who is new to Rover and unsure of whether or not to book.

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Joe S.
Sitter Profile Image: Carole C.
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Carole C.
Star Sitter
from
$80
per night
5.0 out of 5 stars
191 reviews
41 repeat clients
23 years of experience
Murray Hill, Milwaukee, WI, 53211

Carole and Shannon are fantastic house and pet sitters! My A/C unit began leaking while I was gone and Carole was flexible and helpful with accommodating a repair person on several days. My plants are happy, my Great Dane is thrilled, and I'm so glad they were available!

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Marjory C.
Sitter Profile Image: Molly O.
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Molly O.
from
$65
per night
5.0 out of 5 stars
72 reviews
20 repeat clients
18 years of experience
Wick Field, Milwaukee, WI, 53208

Molly absolutely crushed it- I can’t say enough good things. Our dogs have huge personalities, some bizarre behaviors, and special needs (and so does our weird old rental house) and she handled all of it with aplomb. Our resident canine klutz tore his paw pad the night before we left, and even though we totally sprung this development on Molly at the last minute, pro that she is, she jumped in and changed his dressings, kept the area clean, AND kept the dog calm to prevent further injury. He was basically fully healed upon our return. Thanks, Molly! We will be back if you’ll have us- with fewer surprises next time, we hope!

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Lily S.
Sitter Profile Image: Lily S.
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Lily S.
from
$125
per night
5.0 out of 5 stars
66 reviews
18 repeat clients
25 years of experience
Milwaukee, WI, 53212

Lily was a blessing for our family!! This was the very 1st time we have used rover. We ended up adopting a dog 2 weeks before a preplanned vacation. Lily was so patient and understanding with us as we had very little information about our new family member when we booked with her. We were able to leave her with notes on training our new dog had and we gave her the ability to address and immediate concerns with positive training as she saw fit to help her week go smoothly. Lily was able to help bridge the gap with consistent training while we were gone to ensure we didn’t lose precious training time. She was also able to pivot and help address any behavioral issues or quirks that arose that we were unaware of. She even sent us videos and a great description of how she addressed them. She sent updates everyday and didn’t hesitate to reach out with questions. She put away our grocery order before we arrived and made sure to have the house cleaned up and even washed the towels I left out for her. We definitely will be booking with her again.

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Sarah R.
Sitter Profile Image: Lynette F.
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Lynette F.
Star Sitter
from
$60
per night
5.0 out of 5 stars
90 reviews
14 repeat clients
11 years of experience
Milwaukee, WI, 53207

Lynette continues to be a star with our dogs. They are both rescues and have special issues. They love lynette and she is so good with them. Thank you Lyly!!!

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Bill B.
Sitter Profile Image: Emily B.
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Emily B.
from
$25
per night
5.0 out of 5 stars
2 reviews
2 repeat clients
6 years of experience
Riverwest, Milwaukee, WI, 53212

As a first time Rover user, I was SO nervous but Emily was truly amazing. She was communicative with updates/pictures and flexible with timing as I was getting back later than anticipated on the last day. I will be rebooking with her!

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Maya D.
Sitter Profile Image: Catherine R.
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Catherine R.
Star Sitter
from
$70
per night
5.0 out of 5 stars
29 reviews
12 repeat clients
1 year of experience
Murray Hill, Milwaukee, WI, 53211

Catherine did a great job. She took great care of our dog and two cats. She asked a lot of great questions that I wouldn’t have even thought about. Very thoughtful and thorough. We will definitely be asking her to petsit again.

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Douglas S.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$50
per night
4.9 out of 5 stars
51 reviews
22 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha was great! She watched our 2 doodles, one with a bit of an attitude! She sent texts when she had questions and sent us pictures. Will definitely book with her again!

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Marie G.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
21 reviews
9 repeat clients
13 years of experience
Juneau Town, Milwaukee, WI, 53202

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!!

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Dena K.
Sitter Profile Image: Rebecca M.
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Rebecca M.
Star Sitter
from
$38
per night
5.0 out of 5 stars
12 reviews
5 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

Rebecca was phenomenal with my little critters! Excellent communication throughout the week and she was able to adjust last minute to needing to give my dog extra TLC and medication. I highly recommend her for your pet-sitting needs!

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Kristina P.
Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$77
per night
5.0 out of 5 stars
103 reviews
28 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

Emily is incredible with my senior dog, Bernie. She's gentle and patient and is understanding of the unfortunate accident or 2 requiring clean up on some visits. I have peace of mind knowing she will be there for Bernie!

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Kim A.
Sitter Profile Image: Carolina G.
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Carolina G.
Star Sitter
from
$50
per night
4.9 out of 5 stars
39 reviews
8 repeat clients
9 years of experience
Cudahy, WI, 53110

Carolina was super respectful of all of our instructions for caring for the cat and dog. She sent many pictures and videos along with detailed updates. We have no question that they were well taken care of and they were happy when she was here.

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Julia M.
Sitter Profile Image: Elizabeth J.
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Elizabeth J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
34 reviews
7 repeat clients
17 years of experience
Lower East Side, Milwaukee, WI, 53202

Elizabeth was amazing. We need a last minute dog sitter and she came through and saved vacation! She provided plenty of updates, photos, and videos. Our dog sometimes is a little shy coming out of her crate but she loved Elizabeth. We will definitely use Elizabeth's services again!!

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Shaun M.
Sitter Profile Image: Alexandra I.
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Alexandra I.
Star Sitter
from
$80
per night
5.0 out of 5 stars
31 reviews
6 repeat clients
11 years of experience
Juneau Town, Milwaukee, WI, 53202

Alex did a great job with Tucker. She bonded with him immediately, he was feed, walked and pampered. Communication was excellent, we got lots of photos and updates. We will definitely use Alex again

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Phil S.
Sitter Profile Image: Ana B.
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Ana B.
from
$75
per night
5.0 out of 5 stars
227 reviews
38 repeat clients
11 years of experience
Shorewood, WI, 53211

I highly recommend Ana! Very happy with the care and companionship that Ana provided for my senior dog, and I was comfortable with Ana staying in my home. I could tell she paid attention to detail about my dog's typical routine and care requests. Ana's cheerful updates made me smile-- she really seems to delight in dogs and their personalities! She was plenty active with my dog, both walks / outdoor time and playing. Thanks Ana!

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Bridget L.
Sitter Profile Image: Kathryn D.
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Kathryn D.
from
$65
per night
5.0 out of 5 stars
87 reviews
23 repeat clients
14 years of experience
Milwaukee, WI, 53211

It was so nice to have Kathryn stay with Autumn while we were away. Kathryn is sweet, responsive and kind. She sent me several pictures during her time with Autumn..

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marycate r.
Sitter Profile Image: Madeline R.
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Madeline R.
from
$27
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
11 years of experience
Lower East Side, Milwaukee, WI, 53202

Madeline is a great and responsive sitter. She took great care of our boys, and she charmed our skittish boy. He even crawled on her lap... amazing while he is a lovebug he does not usually warm up that quickly.

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Deb R.
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The median cost per night for house sitting in Hillside is $50

Pet parents share their Rover experiences - Hillside

1 / 1
5.0 out of 5 stars

Mikalanne took amazing care of my two dogs and was amazing with her communication. Would definitely book again

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Hannah L.
House Sitting
5.0 out of 5 stars

Keisha deserves a perfect rating for the great care she provided for our dog and the house was in absolutely perfect shape! I can’t say enough about how great she was! When we got home she left our pet with a soothing pet sounds screen saver on the TV. It was such a nice way to be welcomed home!!

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Mark M.
House Sitting
5.0 out of 5 stars

As always, Ashley was incredible watching our pets and our house while we were on vacation. We never have any concerns when she is there and her communication is always incredible. Thanks again, Ashley.

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Dustin G.
House Sitting
5.0 out of 5 stars

Carrianne was a blessing when we first found her after our original dog sitter backed out. At the time, we had two dogs, one elderly dog with more needs and one young 2 year old pup. The first meet and greet when great. She completely understood our elderly dog's needs with mobility and was prepared to take care of both of our dogs when we would be gone for a week. Shortly before our trip, our elderly dog passed. Carrianne was open to another visit with just our younger dog and that went just as well. Unfortunately, we couldn't anticipate how our pup would be when we were gone and not have her buddy with her. Carrianne approached the unexpected behaviors with compassion and understanding, which is all we could ask for. She communicated frequently and was open to any problem solving solutions that would make our pup feel comfortable. She was open to working with our neighbor to give our puppy what she needed in the time of a big life transition for here, with unexpected/unanticipated behaviors while we were gone. If you are looking for someone who understands dogs and dogs needs, I highly recommend Carrianne.

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Katie T.
House Sitting
5.0 out of 5 stars

Great service and very well communicating with me throughout the day. The pup most definitely had fun and enjoyed her time with Kyla

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Jules T.
House Sitting
5.0 out of 5 stars

Very good and fid well communicating and letting me know how the day was going. Ve back to a satisfied dog

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Jules T.
House Sitting
5.0 out of 5 stars

Tabitha was fantastic! She made the process seamless and took excellent care of Newt. I will certainly request her services again!

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Erin L.
House Sitting
5.0 out of 5 stars

This was our second time having Nikki watch our dog for a three night stay, and everything went great as usual. My dog was expertly cared for, walked twice/day, fed and loved. My house was cleaner than we left it! Will definitely hire Nikki again she was great and kept in communication with us during our trip. Thanks again, Nikki!

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Karrie L.
House Sitting
5.0 out of 5 stars

Maddy was absolutely wonderful! She took amazing care of Harley and kept me updated so I could relax knowing Harley was happy and in great hands. I highly recommend Maddy and will definitely book her again!

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Michelle S.
House Sitting
5.0 out of 5 stars

The best house/cat sitter! Our cat was very happy, and she left our house so nice and clean. Amazing.

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Nancy & Daniel N.
House Sitting
5.0 out of 5 stars

We are so grateful to have found Laurie! She spent a week with our 9 month old Bernedoodle puppy, skillfully managing his sometimes "challenging" energies. We appreciated the daily pictures, the regular contact, and her insightful feedback and training tips grounded in her experience with dogs. Our house was well-cared for, and all was well when we arrived home. We also appreciated her managing an unfortunate "casualty" in our aquarium! We would absolutely hire her again. Thank you Laurie!

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Paul S.
House Sitting
5.0 out of 5 stars

Rebecca was great with Hambone. She was communicative and flexible, sent good updates and pics. Will definitely book again!

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Julia S.
House Sitting
5.0 out of 5 stars

As a first time Rover user, I was SO nervous but Emily was truly amazing. She was communicative with updates/pictures and flexible with timing as I was getting back later than anticipated on the last day. I will be rebooking with her!

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Maya D.
House Sitting
5.0 out of 5 stars

Nina stayed with our two dogs for a night. We came home to two happy and well cared for pups and a clean house. I would definitely recommend her!

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Sarah M.
House Sitting
5.0 out of 5 stars

Another great stay with Catherine. Our pup was completely relaxed when we came home and clearly loves having Catherine stay with him!

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Ben B.
House Sitting
5.0 out of 5 stars

Alex stayed at our house with our dog and cat for 3 nights and she was amazing. Super communicative, I loved all of her updates and pictures. I was never once worried about them! She was very respectful of our home - it looked just like we left it. We will definitely request Alex again for our next trip!

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Kathleen P.
House Sitting
5.0 out of 5 stars

Thank you Christie! She did a wonderful job taking care of our pup and our house while we were away. Christie sends great pics and thorough updates throughout her stay and we appreciate all she does!

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Samantha L.
House Sitting
5.0 out of 5 stars

Melissa was amazing with our pups! She took great care of our house and our dogs while we were away. Would use her again in a heartbeat.

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Angela S.
House Sitting
5.0 out of 5 stars

Gabrielle watched our two dogs over the weekend. Our trip was smoother for peace of mind knowing that they were in good hands! She was responsible, gave updates, took them on walks. We came back to happy pups. You'd be fortunate to book her for dog care!

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Savannah T.
House Sitting
5.0 out of 5 stars

This was our third time having Elizabeth stay with our dog. Walks are the highlight of his day and Elizabeth always gets him out for long walks. The house is always in good order upon our return. We are grateful to have found Elizabeth.

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Carol M.
House Sitting
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