Pet Sitting & Drop Ins In Hillside

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Hillside pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Travis H.
Verified Background Check
Travis H.
from
$25
per visit
5.0 out of 5 stars
342 reviews
106 repeat clients
35 years of experience
Riverwest, Milwaukee, WI, 53212

Travis will treat your fur babies as if they were his own! This was our first experience using Rover & we were very satisfied. I would wholeheartedly recommend Travis to take care of your pets while you are away. We had 100% peace of mind & no worries or concerns. We will use him again!!!

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Larry B.
Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
145 reviews
50 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Jackie was great! Kitties were very well taken care of. Pictures were sent throughout of them playing, having treats, etc which was nice to see while we were away! Would definitely use her again!

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Lindsey M.
Sitter Profile Image: Amy N.
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Amy N.
from
$18
per visit
20 years of experience
Lower East Side, Milwaukee, WI, 53202

About: I’m a dog/cat mom who is a little obsessed with animals and can’t wait to meet yours! Open for boarding in my home, walks, check ins, feeding, etc. I currently have a standard poodle and a mini poodle who are the center of my life (let’s face it, the run my life!). They love guests and would be thrilled to meet your dog and cat while you’re away. I have 20+ years of experience with dogs and cats, able to give medications, provide senior care, and daily walks, play time. I’d love to help give your pet their very best life! I work a very flexible schedule and can usually accommodate your needs. I’m available weekends and most holidays as well. I’ll do my best to work together to find the best schedule for your pet. My dogs have a lovely home and they kindly let me live there too. 😆. The dogs are allowed free run of the house at all times, though I do have crates for when they want some unbothered time, at their choice. I live in a great neighborhood filled with dogs so we meet a lot of friends on our walks, too.

Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
204 reviews
63 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica was great! Very responsive and communicative and appreciated how timely her visits were. Our cats seemed to be very happy having her drop in too and we loved all the photos 😊

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Colleen S.
Sitter Profile Image: Autumn J.
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Autumn J.
from
$15
per visit
10 years of experience
Milwaukee, WI, 53206

About: I have had dogs my whole childhood, and been around dogs since I could remember. I understand that every pet has unique needs and I strive to make them feel safe, comfortable, and loved. I had a miniature dachshund growing up- so bonus points for a weenie! 🌭 I’m currently working part-time this summer so I have a lot of time to care for your pets. My schedule is kinda random as I am in healthcare currently. I either work from 7-1pm or 1-8pm. Fridays I have mornings available until 12pm, and Saturday evenings, free Sundays. I have two Maine Coon cats at my home currently. They are very friendly but a little skiddish. We have a litter robot at our home, and they are very spoiled & loved!

Sitter Profile Image: Ilene G.
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Ilene G.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
21 reviews
9 repeat clients
7 years of experience
Riverwest, Milwaukee, WI, 53212

Ilene was a great sitter for our two-year-old kitty! She was very communicative, flexible and laid-back. She was able to come for a meet-and-greet ahead of time and amended the drop-in time, per my request, partway through our trip. We really appreciated her detailed write-ups and quality photos. Thank you, Ilene!

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Annamarie H.
Sitter Profile Image: Alexandra I.
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Alexandra I.
from
$18
per visit
5.0 out of 5 stars
9 reviews
10 years of experience
Juneau Town, Milwaukee, WI, 53202

The pets seemed super happy with Alex’s visit, we’re so excited we found her here on Rover- gives us so much confidence and relief for our pets’ care needs for any future drop ins/stays. Super impressive she was able to get the puppies to cuddle up all together on her first drop-in, they clearly liked her a lot! The photos and updates were great little check ins to see the goobers acting well, enjoying some company, and resting happily. Alex is also amazing at following their specific care instructions and asking any questions to clarify or check for things. Communication is 1000/10, plus super responsive, attentive, and easy to coordinate with. Thank you!

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Stefanie V.
Sitter Profile Image: Avery P.
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Avery P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
54 reviews
14 repeat clients
10 years of experience
Historic Third Ward, Milwaukee, WI, 53202

Avery was great with my dog! Followed all requests and went above and beyond. She was very communicative and accommodating. I would definitely recommend booking with her and I will again too! :)

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Briana O.
Sitter Profile Image: Nina W.
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Nina W.
from
$15
per visit
10 years of experience
Avenues West, Milwaukee, WI, 53233

About: I provide dependable, attentive care and treat every pet like they are my own. I understand that every animal has different needs and personalities, so I take the time to make pets feel comfortable, safe, and loved while their owners are away. I’m patient with shy or anxious pets, energetic with playful dogs, and gentle with senior animals who may need extra support and slower-paced care. I’m also very detail-oriented and make sure routines are followed closely, including feeding schedules, medications, walks, potty breaks, and playtime. I communicate consistently with pet owners through updates and photos so they always know their pet is happy and well cared for. What sets me apart most is the amount of genuine attention and affection I give to each pet. I don’t just “watch” animals — I spend quality time with them to make sure they feel comfortable, engaged, and cared for while you’re away. I'm currently nannying on weekdays from 8:00am - 4:30 pm, so I’m available for morning visits before work, evening walks/check-ins, and overnight care depending on the pet’s needs. I’m especially flexible on weekends and have much more availability for walks, drop-ins, extended stays, and quality playtime. When caring for pets in a client’s home, I focus on keeping their routine consistent, stress-free, and fun. I make sure pets are fed on schedule, get plenty of exercise, attention, and playtime, and feel comfortable while their owners are away. I have experience with dogs of all sizes. I have two large-breed dogs at home, so I’m comfortable handling bigger, high-energy dogs, and I have also frequently dog sat for smaller-breed dogs with different temperaments and care needs. I’m reliable, detail-oriented, and always follow owner instructions closely, including feeding schedules, walks, medications, and any special care requests.

Sitter Profile Image: Nevaeh T.
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Nevaeh T.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
24 reviews
6 repeat clients
6 years of experience
Milwaukee, WI, 53211

Nevaeh was awesome! She sent us text updates including pictures/videos the whole time giving us peace of mind. Our dog Mallie loved her! Would definitely recommend!

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Cheyenne D.
Sitter Profile Image: Katarina N.
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Katarina N.
from
$15
per visit
4.8 out of 5 stars
16 reviews
13 repeat clients
10 years of experience
Historic Third Ward, Milwaukee, WI, 53202

Kat was great! She took the time to get to know Lily. She was punctual, great communication, and she sent pictures. I would use her again for sure.

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Liz C.
Sitter Profile Image: Zoe M.
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Zoe M.
from
$18
per visit
11 years of experience
Milwaukee, WI, 53202

About: I’ve been a pet sitter since I was a kid and i’ve loved every second of it. I know that each animal is different and i’m prepared to give your pet the care it deserves. I’m working part time with a flexible schedule but I am mostly unavailable in the mornings. I will be more available in the late afternoon and night. I have been around dogs my whole life so I am experienced in the needs of dogs in their homes. I always prioritize the pets safety according to their owners instructions.

Sitter Profile Image: Megan D.
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Megan D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
58 reviews
14 repeat clients
11 years of experience
Milwaukee, WI, 53204

Megan was so wonderful!! Our sassy cat loved her and we could tell he felt comfortable with her and was calm when we got home after a week away. We are so thankful to have found her and are way more confident with leaving in the future!

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Anika H.
Sitter Profile Image: Qian D.
Verified Enhanced Background Check
Qian D.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
2 years of experience
Lower East Side, Milwaukee, WI, 53202

Qian took great care of my cat while I was away. She came to my house every day for a week!, refreshed his water, cleaned the litter box, and spent time playing with him. She was reliable, consistent, and made me feel very comfortable knowing my cat was nice and cared for. I really appreciated her help and would definitely recommend her to anyone looking for a trustworthy pet sitter!

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Just N.
Sitter Profile Image: Lesley R.
Verified Enhanced Background Check
Lesley R.
from
$15
per visit
6 years of experience
Brewer's Hill, Milwaukee, WI, 53212

About: I’ve dog & cat-sitted for friends, neighbors, and family somewhat frequently over my life. I also used to travel when I first adopted my own cats, so I understand how important it is to trust the person looking after your animal. I prefer to stick to the animal’s routine as much as possible - I find it’s less stressful for them. On the days I’m available, I can flex to a customer’s needs. It’s all about the animal more than it’s about me. Routines are important, so I would want to stick to yours. Also, if you’re gone longer than a weekend/days I’m available, feel free to reach out. I have an unusual work schedule, and if I’m a good fit for you & your pet, I am happy to be flexible beyond what’s “officially” listed as my availability. I’m also happy to get mail, water plants, and I always wash food/water bowls for the pets I visit. I live in a condo very close to downtown. The neighborhood is very walkable. Because I traveled for work, sometimes at the last minute, I also accept last minute appointments - because those can be stressful enough! It’s nice knowing you can count on someone on short notice.

Sitter Profile Image: Hope S.
Verified Enhanced Background Check
Hope S.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
51 reviews
24 repeat clients
15 years of experience
Riverwest, Milwaukee, WI, 53212

Hope was so amazing with my kitty! She left very detailed notes, giving me complete peace of mind while I was dealing with a loss in the family. Hope was extremely communicative and responsive which was very helpful. She not only made sure my kitty’s basic needs were met, but went above and beyond to play with her, too. Very grateful for a phenomenal sitter like Hope. 😇

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Sarah R.
Sitter Profile Image: Riley L.
Verified Enhanced Background Check
Riley L.
from
$15
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
3 years of experience
Avenues West, Milwaukee, WI, 53233

About: Hi! I would be an amazing pet sitter because I love animals. Ever since I was little I have had pets whether dogs, cats, ducks or turtles. I am currently in college and away from my dog Nalla so taking care of your pet would honestly be special for me too. One of the main reasons I am on rover is because I love to walk and hike and figured why not add a companion. Hi! I am currently on break from work and school so I can make anything work! I am available everyday of the week at any hours necessary! I sadly cannot have any pets in my home because I live in an apartment but I can take that out for walks in areas near me! I also am used to taking care of a dog when I am home so can do whatever the owner needs!

Sitter Profile Image: Jamie S.
Verified Background Check
Jamie S.
from
$14
per visit
5.0 out of 5 stars
28 reviews
13 repeat clients
17 years of experience
Avenues West, Milwaukee, WI, 53233

This was my first time using Rover, and I couldn’t have asked for a better dog lover, than Jamie. Jamie was fantastic to work with, and has great communication. I look forward to working with her in the future.

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Edward S.
Sitter Profile Image: Mary Beth B.
Verified Enhanced Background Check
Mary Beth B.
from
$14
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
2 years of experience
Avenues West, Milwaukee, WI, 53233

Mary Beth was great! She did drop in visits with Winnie this summer while I was at work and was a huge help. She’s very trustworthy, communicates well, and I always knew Winnie was in good hands. Thanks Mary Beth!

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Annie K.
Sitter Profile Image: Jake R.
Verified Background Check
Jake R.
from
$25
per visit
5.0 out of 5 stars
13 reviews
3 repeat clients
10 years of experience
Brewer's Hill, Milwaukee, WI, 53212

About: I've grown up with dogs since I was 8 years old and have loved taken on the responsibilities. I also have experience taking care of friends' and family's variety of pets. I currently have my own 1 year old Australian Shepherd who has taught me so much about raising and training a dog. I will give your pets the attention, time, and patience that they deserve. I currently work remotely so I am very flexible with providing pet care and ensuring that your pets get quality time! I love spending time walking, playing fetch, or exercising with my dog everyday and would love to do the same with yours. I am always thoughtful of a pet's needs and am respectful of their space. I practice good spatial awareness with my own high energy dog and understand how important it is to properly monitor a pet's behavior. I currently have availability at any time of day throughout the week. For my own pets, I ensure that they are properly fed and watered throughout the day. All of them have designated time to play each day and are groomed regularly. I will give this same attention to care to any animal I watch and am responsible for. While house sitting or dropping, I follow instructions given to me as best I can and I respect you and your pets' space. Whatever is best for you, I will accommodate!

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Over 4
pet parents in Hillside have booked pet sitting

Hillside pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Qian is reliable as always! Always appreciated that she takes photos with the drop in! Definitely top pet sitter!

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Pei Hsuan C.
Drop-In Visits
5.0 out of 5 stars

Katie provided peace of mind and lots of great love and attention to my two dogs. I can’t wait to have her help again in the future!!

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Tonya N.
Drop-In Visits
5.0 out of 5 stars

Travis was amazing and able to help on such short notice. The photos were great, and Pretzel looked so happy!

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Laura B.
Drop-In Visits
5.0 out of 5 stars

Abigail is the best. We've utilized her services 4 or 5 times over the last few years and she's always reliable, communicative and pleasant to work with. I can't overstate our satisfaction.

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Brian S.
Drop-In Visits
5.0 out of 5 stars

Lindsay did an exceptional job caring for my dog while I was away. She was highly communicative throughout the entire stay, spent quality time with him, and regularly sent updates and photos that gave me peace of mind during my trip. It was clear that she genuinely cared about his well-being and made sure he was comfortable and happy. I would absolutely trust Lindsay with my dog again and highly recommend her to anyone looking for a reliable and caring pet sitter.

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Patrick S.
Drop-In Visits
5.0 out of 5 stars

The pets seemed super happy with Alex’s visit, we’re so excited we found her here on Rover- gives us so much confidence and relief for our pets’ care needs for any future drop ins/stays. Super impressive she was able to get the puppies to cuddle up all together on her first drop-in, they clearly liked her a lot! The photos and updates were great little check ins to see the goobers acting well, enjoying some company, and resting happily. Alex is also amazing at following their specific care instructions and asking any questions to clarify or check for things. Communication is 1000/10, plus super responsive, attentive, and easy to coordinate with. Thank you!

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Stefanie V.
Drop-In Visits
5.0 out of 5 stars

appreciated Jessica popping over to reacquaint herself with my pup and house etc before our booking. she did all we talked about in 2 timely drop in visits and kept me informed. highly recommend!

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Jude S.
Drop-In Visits
5.0 out of 5 stars

Sarah was great! Our cat who is normally very shy around strangers clearly felt comfortable enough to let Sarah pet her.

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Stacey M.
Drop-In Visits
5.0 out of 5 stars

Anna took wonderful care of my two stranger-shy cats, even managing to coax one of them out of hiding, a minor miracle! Will definitely be booking again!

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Brad B.
Drop-In Visits
5.0 out of 5 stars

Carole (and Max!) were terrific help with twice-daily drop-ins to give an antibiotic -averse Great Dane his meds. They were patient and kind, in spite of his trixie wiles!

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Marjory C.
Drop-In Visits
5.0 out of 5 stars

Vanessa is so incredibly attentive and sweet to our pets. We know they are always well cared for and loved when we have to get away. She’s a blessing!

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Miranda B.
Drop-In Visits
5.0 out of 5 stars

Liz was amazing! She was so sweet to our two cats and took excellent care of them. She also took her son over to visit them one night and he was great with them. Can’t recommend her enough, we are immediately rebooking for our next weekend trip.

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Jackson H.
Drop-In Visits
5.0 out of 5 stars

Christie did a phenomenal job taking care of our pup! She is great with him and very communicative throughout each drop in.

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Samantha L.
Drop-In Visits
5.0 out of 5 stars

Maggie was easy to work with, very responsive, and had an amazing time with my pup. Would love to have her watch my dog anytime!

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Bo B.
Drop-In Visits
5.0 out of 5 stars

Aubrey is an attentive and caring kitty sitter who is easy and friendly to communicate with. We’ve hired her more than once when vacationing and will definitely do so again!

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Amanda R.
Drop-In Visits
5.0 out of 5 stars

Helped me out with a last minute request for a pet sitter. Communicated very well and did everything asked! Would rebook again in future 😊

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Payton H.
Drop-In Visits
5.0 out of 5 stars

Amazing as usual! Thank you and I know gizmo and Daisy are grateful as well for your warm and friendly visits.

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Kailey S.
Drop-In Visits
5.0 out of 5 stars

Bailey is always awesome and I love her updates!! She does a great job with the kitties and takes great pics!

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Jaclyn W.
Drop-In Visits
5.0 out of 5 stars

Jackie was very kind! I appreciated her looking after my fur babies while I was gone. I always loved the picture updates!

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Samantha M.
Drop-In Visits
5.0 out of 5 stars

Amazing care for our cats! Great updates throughout the trip that left us feeling comfortable knowing our kitties were well taken care of

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Jensen M.
Drop-In Visits
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Pet Sitting FAQs

Frequently asked questions about Rover

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

If you have an active request or have booked a service with a pet 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 pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

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

Rover makes it easy to find Hillside pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet 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 pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.