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: Alexandra I.
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Alexandra I.
Star Sitter
from
$70
per night
5.0 out of 5 stars
22 reviews
4 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: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
17 reviews
8 repeat clients
13 years of experience
Juneau Town, Milwaukee, WI, 53202

Ashley took absolutely excellent care of our cat while we were out of the country for a week! I knew from the moment she met our cat during our meet and greet that our little girl was going to be in great hands. Throughout the trip, Ashley reached out with check-ins and photos reflecting how well she was being taken care of. She also responded quickly to any messages and went above and beyond watching our place. We (and our cat) look forward to seeing her again in the future!

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Jeremiah W.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$45
per night
4.9 out of 5 stars
47 reviews
22 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha was amazing with our 10 year old dog! This was our first time using a sitter and it went so smoothly. We got tons of pictures updates and Keisha left the house in tip top shape. I highly recommend working with her! Best of the best!

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

Elizabeth took amazing care of our dog Layla while we were away. She kept us updated with sweet messages and photos, and we could tell Layla was happy and well-loved the whole time. We came home to a relaxed, content pup — we couldn’t ask for more! Highly recommend Elizabeth and would absolutely book with her again.

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Monique M.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$64
per night
5.0 out of 5 stars
208 reviews
63 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Our family had recently experienced a loss of our other pet. It was a tough time for travel but Jessica supported our other pet while we were away. She kept us informed and made the world of difference being away during such a difficult time.

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

We were so happy to have Carole staying at our house and taking care of our puppy! We were sent many updates and assured that our dog had been well taken care of. Thank you!

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Catie W.
Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$90
per night
5.0 out of 5 stars
147 reviews
54 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: Rebecca M.
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Rebecca M.
from
$28
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

About: I’ve been caring for dogs for over 5 years, and I truly love getting to know each pet’s personality and routine. Friends, neighbors, and family have trusted me to walk, feed, play with, and stay with their pets while they’re away. I especially enjoy longer stays because it gives dogs time to feel comfortable and settled, and I love being able to build that trust with them. One of my favorite parts is taking dogs on enriching walks, keeping them active, engaged, and happy, and making sure they feel safe, loved, and well cared for while their owners are away. I work remotely, which gives me a flexible schedule and allows me to give pets plenty of attention throughout the day. I’m able to keep up with walks, feeding schedules, playtime, potty breaks, and companionship, especially during longer stays when consistency and routine are important. I always try to make pets feel as comfortable and relaxed as possible by sticking closely to their normal routine and giving them lots of attention and care. I pay close attention to each dog’s personality, energy level, and needs to make sure they feel safe, happy, and comfortable while their owners are away. I’m attentive on walks, respectful of clients’ homes, and committed to providing reliable communication and updates throughout each stay.

Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$59
per night
5.0 out of 5 stars
38 reviews
9 repeat clients
30 years of experience
Milwaukee, WI, 53213

Emily did a fantastic job watching Tuukka while we were traveling to India for a wedding. She sent daily updates with lots of photos and we knew our pup was well take care of when we were away!

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Anna C.
Sitter Profile Image: Julianna W.
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Julianna W.
from
$44
per night
5.0 out of 5 stars
13 reviews
1 repeat client
30 years of experience
Milwaukee, WI, 53204

Julianna Stayed in my house for five nights/six days and took excellent care of my large, high-energy Siberian Husky. It can be hard to find a trustworthy house/dog sitter sitter outside of personal friends and family, but I couldn’t have been more satisfied.

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

Megan was friendly and super communicative the whole time she house sat for us! My dog got sick while I was away and Megan handled it like an absolute pro. I would definitely trust Megan to care for my dog again.

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Amanda J.
Sitter Profile Image: Melissa H.
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Melissa H.
Star Sitter
from
$70
per night
5.0 out of 5 stars
57 reviews
22 repeat clients
40 years of experience
Milwaukee, WI, 53202

Wonderful!!! Charlie was so relaxed when I got home which I think speaks volumes to how comfortable he was with Melissa. They played, cuddled and went for a bunch of walks. I loved the photos!!❤️ I will definitely be booking Melissa again for my sweet little peanut!

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Mary Elizabeth W.
Sitter Profile Image: Catherine R.
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Catherine R.
Star Sitter
from
$70
per night
5.0 out of 5 stars
26 reviews
10 repeat clients
1 year of experience
Murray Hill, Milwaukee, WI, 53211

Catie is a gem! We met twice before she stayed with our two small dogs for 4 nights. Catie updated us frequently and left our house spotless… and our dogs love her! She is kind, highly reliable, a great communicator and is a truly lovely person. So happy to have found her!

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Joshua S.
Sitter Profile Image: Jake R.
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Jake R.
from
$55
per night
5.0 out of 5 stars
13 reviews
4 repeat clients
10 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Watson had his first dog watching experience and we are so happy it was with Jake . He took great care of Watson and sent updates and pictures .

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Bryn M.
Sitter Profile Image: Alena H.
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Alena H.
from
$55
per night
4.9 out of 5 stars
7 reviews
16 years of experience
Milwaukee, WI, 53233

Alena did a great job taking care of my pup! I booked on short notice, and she was extremely gracious and accommodating, and even she made time for a meet and greet prior. She was prompt in responses when I reached out and sent check-in updates and photos as well. I would definitely recommend and will be rebooking if the need arises!

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Mandy S.
Sitter Profile Image: Riley L.
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Riley L.
Star Sitter
from
$35
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
3 years of experience
Avenues West, Milwaukee, WI, 53233

Overall, it was great! She sent us photos throughout our trip and took good care of the dogs. Whenever we reached out (i.e. - packages, workers coming to the house), she was responsive and would grab anything to help. She also treated our house with respect and left it better than she found it - taking out the trash before she left even! Before she left, she even washed the sheets to her bed and started a load of towels - which was unexpected but awesome to be able to get a head start on laundry. Would definitely recommend and will plan on contacting her for future house sitting needs.

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Edward C.
Sitter Profile Image: Alhana S.
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Alhana S.
from
$45
per night
4.7 out of 5 stars
7 reviews
4 repeat clients
10 years of experience
Murray Hill, Milwaukee, WI, 53211

Alhana was great with Coco. My little dog was recovering from knee surgery and she followed instructions beautifully for he night I had to be away. Thank you!

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

This is our first time using Rover and I am so glad that Lily was the one to watch Rosie. She did a great job keeping us updated, sending pictures and it looks like she and Rosie had a blast. She even did a little training for us. I highly recommend Lily and we will definitely use her again in the future.

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Mary I.
Sitter Profile Image: Kathryn D.
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Kathryn D.
from
$65
per night
5.0 out of 5 stars
86 reviews
22 repeat clients
14 years of experience
Milwaukee, WI, 53211

Kathryn has been amazing! She picked up a request super last minute and was so sweet to my pup. She really goes above and beyond what a typical dog watcher would do. Would definitely recommend!!

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Emily H.
Sitter Profile Image: Lauren S.
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Lauren S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
10 years of experience
Kilbourn Town, Milwaukee, WI, 53203

Lauren did a great job taking care of the boys while we were away. She gave them plenty of exercise and engagement as well as keeping them on their regular schedule. Very much appreciated and we hope to book again.

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Alex J.
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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

Elizabeth did a great job as always!! She is such a great communicator and sends so many pictures which I love! Thank you so much!!

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Emily H.
House Sitting
5.0 out of 5 stars

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.
House Sitting
5.0 out of 5 stars

Kyla was beyond amazing & wonderful with my 2 cats! She took time to observe & learn how I normally do my pet care; she even came over a day before I left so she could feed, change water, clean litter box, use the vacuum & empty it, etc…. My boys LOVED HER from the first day they met her. She updated me with photos, videos & messages about them which was really fun & much appreciated..Kyla was very respectful of my living space…she even cleaned it and did laundry before I came back home!! She took the cats on walks, took time to acquaint herself with staff & people in my building. She left a lovely card for me. My goodness… I just can’t say enough to describe how pleased & grateful I am for Kyla & her incredible love & care of my cats as well as her respect for me & the whole community I live in. She will be welcomed back in a heartbeat!

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Kimberly S.
House Sitting
5.0 out of 5 stars

Highly recommend Carole! Excellent communicator, clean and polite in our home, and our dogs were SO well cared for!

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Ashleigh D.
House Sitting
5.0 out of 5 stars

Madeline house sat for me for over a week and did a great job with my timid Chihuahua and Cat. She gave me daily updates and handled their daily routine and activity needs effortlessly. My dog who's slow to warm up to new people was actually sad to see her leave by the end of the sitting period. Highly recommended.

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Ryan O.
House Sitting
5.0 out of 5 stars

Alena did a great job. Cosmo seemed to be really well taken care of was very calm when we got back. Alena also left the house in great shape.

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Ronald S.
House Sitting
5.0 out of 5 stars

Cassidy was great! Very communicative, responsible and trustworthy! She sent pictures and took very good care of our dogs! We would love to have her stay with them again for sure!

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Shelley M.
House Sitting
5.0 out of 5 stars

Thanks so much Yacob! Appreciate all you do for our Harvey. We are licky to have you and your support.

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Nick A.
House Sitting
5.0 out of 5 stars

Jamie was simply amazing & incredibly reliable! I was in the UK for nearly one full month and Jamie house sat with my two dogs and two cats. One of my dogs is very high energy and the other is 15. During my travels, my older dog, Macy, developed a second round of vestibular disease. Jamie immediately noticed the change in Macy's coordination and reached out to me. We coordinated a same-day visit to the vet, followed by regular medication. The condition required Jamie to carry Macy up and down the stairs for the remainder of the sit. Jamie took care of Macy while still ensuring my high-energy dog got the play time he needed. I cannot say enough about Jamie's dedication and communication skills. Highly recommend!

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Kristin S.
House Sitting
5.0 out of 5 stars

Lily absolutely exceeded my expectations with her attention to detail, genuine care and concern for my pups, and thoroughness! My dogs were well taken care of with feeding, walking (carefully in a heat wave), fireworks, and just general companionship. I also returned to my home probably looking better than how I left it - well cared for, cleaned, and plants alive and well. The daily updates were fantastic and very reassuring. Lily is amazing and I hope we can book again :)

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K D.
House Sitting
5.0 out of 5 stars

Alex was amazing with my dogs! She sent updates throughout the stay and took great care of my house. My dogs receive medications and she handled it all amazingly!

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Stefanie S.
House Sitting
5.0 out of 5 stars

Travis took incredible care of our two dogs and handled a genuinely chaotic situation with so much calm and flexibility. The night before we left, our AC failed during a heat wave. While we were stuck across the country juggling an HVAC company and a landlord who wasn’t prioritizing the issue at all, Travis kept the dogs safe, comfortable, and monitored. He checked in regularly so we knew how they were doing, and he adjusted his schedule so repairs could be made. His support made a huge difference for our peace of mind during a very stressful situation for us and I’m sure him. One of our dogs is anxious, skittish, and extremely high‑energy, and Travis did an amazing job letting her warm up at her own pace while still getting her out for consistent walks. Both dogs were well cared for the entire stay. We’re so grateful for how he handled everything and will absolutely book with him Again. Thank you Travis!

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Charlotte B.
House Sitting
5.0 out of 5 stars

Elizabeth was awesome, and super flexible when my travel plans got switched up at the last minute. Will definitely rebook!

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Margaret G.
House Sitting
5.0 out of 5 stars

Nikki went above and beyond for our dog and two birds when house sitting for us! We received regular pictures and updates and they were well cared for.

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Barret S.
House Sitting
5.0 out of 5 stars

Ashley took great care of my pet and my home!! She was very reliable and great about sending updates. I would absolutely book her again!

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Kristen H.
House Sitting
5.0 out of 5 stars

Riley was wonderful with our boys. They are relatively recent rescues, so have some behavioral quirks. Riley quickly sussed out how to approach the boys. She sent regular updates and photos, which I so appreciated!! I wouldn't hesitate to have her stay with Rocky and Gordo anytime!

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Cathi W.
House Sitting
5.0 out of 5 stars

Kiara was so happy to see Melissa, and we could be out for the evening knowing our pup was in good hands.

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Kristin S.
House Sitting
5.0 out of 5 stars

Lauren was great! She stayed with my pups while I was at summerfest for the day. She was so responsive, gave updates, and my boys loved her. She was extremely respectful of my space and even sent a video of locking the door and giving the key back since I wasn’t home yet. Will be using her services again!

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Emma P.
House Sitting
5.0 out of 5 stars

As always, Megan was amazing with our fur babies! I could tell they felt happy and safe while we were away which is the best feeling! Thank you!!

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Emily H.
House Sitting
5.0 out of 5 stars

First time user of Rover, and we love Sydney! Our dogs loved her, which one of our dogs is not a fan of strangers. But he approved so much that he jumped up and cuddled next to her immediately. Which DOES NOT happen! She was thorough with asking questions. We will be using Sydney again!

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Melissa R.
House Sitting
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Sitters in Hillside average 4
repeat house sitting clients

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