House Sitting In Hillside

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Top rated Hillside house sitters

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: Rachel H.
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Rachel H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
101 reviews
25 repeat clients
11 years of experience
West Allis, WI, 53214

We were so happy Rachel was available for the holiday weekend. We didn’t have to worry about about leaving our beloved dogs at all because Rachel is a pro! She books up quickly for a reason!

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STEPHANIE R T.
Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$59
per night
5.0 out of 5 stars
25 reviews
6 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: Elizabeth C.
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Elizabeth C.
from
$45
per night
5.0 out of 5 stars
15 reviews
7 repeat clients
7 years of experience
Wauwatosa, WI, 53213

Libby was wonderful with taking care of my cat and dog! She made sure they were both safe, fed and exercised. She also did extra house needs, like taking in the mail, watering the flowers and attending to my garbage cans on weekly pick-up! Highly Recommended!

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Barbara B.
Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$77
per night
5.0 out of 5 stars
96 reviews
26 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

Emily was prompt, respectful, and communicative. She sent pictures and updates and my dog seemed very comfortable and calm when I returned. I highly recommend Emily and will happily book her again in the future if I need a dog sitter!

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Meredith H.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$64
per night
5.0 out of 5 stars
195 reviews
54 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: Megan D.
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Megan D.
Star Sitter
from
$75
per night
5.0 out of 5 stars
52 reviews
13 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: Elizabeth J.
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Elizabeth J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
27 reviews
6 repeat clients
17 years of experience
Lower East Side, Milwaukee, WI, 53202

Elizabeth did the most fantastic job with our dog Annie. She was always fast to respond and sent multiple updates with pictures! Annie can be reactive and has grudges against many of our neighbors dogs so leaving her with someone new for neighborhood walks can be daunting. I felt completely confident in Elizabeth after one walk with her and Annie. We will absolutely be reaching back out to Elizabeth the next time we are looking for a rover! Thank you so much for the best first rover experience.

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Emma L.
Sitter Profile Image: Keisha P.
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Keisha P.
from
$45
per night
5.0 out of 5 stars
38 reviews
17 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

We had Keisha stay for a 7 day sit for our dog and cat. Keisha was incredible and everything we could have ever wanted in a sitter! She sent us updates at least daily, sometimes more with pictures which is what we requested! I made an error and she was flexible with adding another day to her stay! Could not recommend her enough, we will definitely use her again in the future!!

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Jordyn
Sitter Profile Image: Lauren S.
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Lauren S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
14 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.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
13 reviews
4 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: Lily S.
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Lily S.
Star Sitter
from
$125
per night
5.0 out of 5 stars
61 reviews
18 repeat clients
25 years of experience
Milwaukee, WI, 53212

As always, Lily goes above and beyond. Helped navigate an u expected, significant GI problem with one of the dogs that required a visit for emergency care and helping mitigate a significant clean-up job. Communicated fantastically throughout the saga

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Eric M.
Sitter Profile Image: Catherine R.
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Catherine R.
Star Sitter
from
$70
per night
5.0 out of 5 stars
18 reviews
7 repeat clients
1 year of experience
Murray Hill, Milwaukee, WI, 53211

Catherine did a wonderful job house sitting. She took attentive care of our two dogs and cat. She provided great updates and our dogs looked so happy in every picture. We had total peace of mind with Catherine watching our home.

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Bill K.
Sitter Profile Image: Carole C.
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Carole C.
Star Sitter
from
$80
per night
5.0 out of 5 stars
176 reviews
39 repeat clients
23 years of experience
Murray Hill, Milwaukee, WI, 53211

I was away for 10 days in July, the longest I’ve ever left my dog, Miley. Once again, Carole was wonderful and was Max. Miley takes time to warm up to people and she’s great with Carole and Max—it’s a relief knowing that Miley is in such good hands!

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Robin F.
Sitter Profile Image: Karla D.
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Karla D.
from
$45
per night
4.8 out of 5 stars
11 reviews
5 repeat clients
5 years of experience
Juneau Town, Milwaukee, WI, 53202

Karla was amazing!! She was super responsive and sent many updates each day we were gone. Kuzco is still a puppy and can be wild at times, and she handled him perfectly. Would use her again for sure!

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Kelsey H.
Sitter Profile Image: Berenice B.
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Berenice B.
from
$70
per night
4.9 out of 5 stars
247 reviews
102 repeat clients
15 years of experience
Bay View, Milwaukee, WI, 53207

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

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Jagpreet S.
Sitter Profile Image: Cindy H.
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Cindy H.
from
$60
per night
5.0 out of 5 stars
51 reviews
12 repeat clients
45 years of experience
Martin Drive, Milwaukee, WI, 53208

We love having Cindy to house sit our dog ! Besides taking care of the dog, she does so many other little things to show how much she cares for the people and animals she takes care of!

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

Jackie was absolutely wonderful! Not only did she take excellent care of our high-need 16.5-year-old dog, she also took great care of our home. She provided updates along the way and followed all of our instructions for caring for Jack (no small feat). We can't speak highly enough about Jackie.

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Kristen R.
Sitter Profile Image: Meghan E.
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Meghan E.
from
$63
per night
5.0 out of 5 stars
21 reviews
3 repeat clients
8 years of experience
Avenues West, Milwaukee, WI, 53233

Meghan was amazing! Our dog loved her and she made sure he is comfortable and happy while we were gone. She sent us multiple updates with pictures of our sweet little pup. She followed all his feeding and walking routines to the t and communication was stellar. We couldn’t be happier. Our Shurik definitely found a new friend.

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Lidia S.
Sitter Profile Image: Maiah D.
Verified Enhanced Background Check
Maiah D.
Star Sitter
from
$100
per night
5.0 out of 5 stars
84 reviews
26 repeat clients
16 years of experience
Juneau Town, Milwaukee, WI, 53963

Maiah did a terrific job taking care of my dog. She gave us daily updates and photos, left the house clean and even stayed with my dog so she didn’t get lonely! Amazing!

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Will S.
Sitter Profile Image: Julianna W.
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Julianna W.
from
$50
per night
5.0 out of 5 stars
10 reviews
1 repeat client
30 years of experience
Milwaukee, WI, 53202

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.
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Hillside pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Davina was truly incredible! I have a dog with many allergies, and is anxious and reactive. She sent me all the updates and he is pooped after her stay. I had such a peace of mind while I was gone, so I cannot recommend Davina enough!! 10/10

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Hailey Q.
House Sitting
5.0 out of 5 stars

Catherine did a great job house sitting and pet sitting my golden retriever for 5 nights. She was extremely professional throughout the entire process and left my home clean and tidy. I would not hesitate to book with her again!

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Kirstyn W.
House Sitting
5.0 out of 5 stars

Jessica is an absolute pro when it comes to dogsitting. We recently rescued two dogs, and they can be quite a handful as they're acclimating to their new home. She was unfazed with Rocky's barking, and had Gordo snuggling in no time. Jessica sent regular updates and photos, which made me feel better, since it was our first time away from them overnight. I highly recommend Jessica, and would love to have her back in the future.

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Cathi W.
House Sitting
5.0 out of 5 stars

We love Talor and so do our doggies. We were gone for 9 days, Talor took such good care of dogs and the house. We will most definitely use her again.

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Diana W.
House Sitting
5.0 out of 5 stars

Harvey is lucky to have you. Thanks for another great long week stay to watch Harvey on our spring break. It’s so nice to know we have someone we can trust.

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Nick A.
House Sitting
5.0 out of 5 stars

Flor was an EXCELLENT sitter to our dog Toast! We left on a trip for 5 days and she took amazing care of not only our dog, but our house as well! She was a great communicator and sent a ton of pictures! She also was great at giving our dog his medicine. We would absolutely book Flor again!

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Santiago M.
House Sitting
5.0 out of 5 stars

It was our second time hiring Elizabeth, another positive experience. My pooch likes his walks and we are grateful she is ok with taking him. She is great with giving updates and sending photos. Upon return the house was just as we left it.

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Carol M.
House Sitting
5.0 out of 5 stars

Steely my dog was in great hands with Megan. He was very happy to see her when she came back after the meet and greet. She kept me up to date regularly and sent me multiple pictures a day which made me feel so good being away. She asked appropriate questions regarding his care instructions. Also the residents in my 55 and over apartment building were very complimentary about her. I would absolutely have her take care of my boy again. Thank you Megan!🩷

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Lyanne H.
House Sitting
5.0 out of 5 stars

Carrianne is fantastic. She befriended my shy cat on their first meeting. Great and responsive at communicating about everything. Completely understood the medication schedule and carried it out. Really grateful to have found someone so responsible and caring.

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Eleanor H.
House Sitting
5.0 out of 5 stars

Travis always goes beyond the call of duty! He is amazing with our dog, communicative and always leaves our place nice and tidy after his stay. If I could give more than 5 stars I would :)

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Rosy R.
House Sitting
5.0 out of 5 stars

Once again, Lily exceeded our expectations. She was so caring and attentive to Bailey during her 11 day stay in our home. She handled a long stretch of horrible weather (including a power outage) and sent us pictures that showed how much Bailey was enjoying playtimes, walks, and cuddles in our absence. The house was in great condition when we returned.

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Susan W.
House Sitting
5.0 out of 5 stars

Lauren is a great pet sitter. She communicated very well and the dogs were happy and healthy when I got home

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Christina J.
House Sitting
5.0 out of 5 stars

Keisha was absolutely great with our young dog. We were feeling anxious as it was our first time leaving him for vacation. She provided constant updates to ease our worried minds and took great care of him and our apartment. We came home to a happy, healthy pup and a clean home. What more could you ask for? If we go on a trip again while living in the area we will 100% be booking with Keisha again. 5/5 stars no complaints.

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Jack D.
House Sitting
5.0 out of 5 stars

Alexandra was fantastic! I have two cats and two dogs, all with quirks, and she was wonderful with them. She put up with more than she was likely prepared for and did so with grace!

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Kristin S.
House Sitting
5.0 out of 5 stars

I’m so thankful I found Carole two years ago! She’s amazing with my senior dog, Miley! Carole is communicative and so in-tune with Miley’s needs—she’s the best and I can’t imagine anyone else caring for Miley.

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Robin F.
House Sitting
5.0 out of 5 stars

Madison’s watched our 1yo hound puppy overnight twice now - once with a cone and once without. Both times were easy, without any problems!

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Nick W.
House Sitting
5.0 out of 5 stars

Erica was thorough, communicative, thoughtful, and loving with our two dogs and cat. It was so refreshing to go away knowing they were in competent hands!

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Jennine P.
House Sitting
5.0 out of 5 stars

Jamie was great with our two pups! She kept us updated and sent lots of photos and took good care of our good boy and girl!

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Heather D.
House Sitting
5.0 out of 5 stars

Maiah did a wonderful job taking care of my buddy. I would recommend her everytime! She sent cute photos along the way!

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Sean R.
House Sitting
5.0 out of 5 stars

Jamie was great! She helped make my usually anxious cat calm and comfortable. She was also great at communicating. I would 100% recommend her!

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Adia H.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 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?

  • 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 house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Hillside house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Hillside.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Hillside house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.