House Sitting Hillside

Find a loving house sitter to watch over your pets and your home.

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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: Allison B.
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Allison B.
Star Sitter
from
$50
per night
4.9 out of 5 stars
40 reviews
6 repeat clients
8 years of experience
Janesville, WI, 53546

We all loved Allison! The boys were well taken care of! She left my home perfect! Thank u Allison i will definitely ask u again for Sailor and Bear!

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Cynthia J.
Sitter Profile Image: Dayna V.
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Dayna V.
Star Sitter
from
$75
per night
5.0 out of 5 stars
19 reviews
4 repeat clients
25 years of experience
Stoughton, WI, 53589

Dayna was amazing! She sent us updates through our trip, including photos. She made our trip so much more relaxing knowing our pups and kitty were in good hands! You won’t be disappointed if you hire her!

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Jessica L.
Sitter Profile Image: Brianna L.
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Brianna L.
from
$45
per night
5.0 out of 5 stars
2 reviews
7 years of experience
Edgerton, WI, 53534

Bri was available on short notice to watch our senior dog. She put our mind at ease knowing she was caring for our sweet boy. She is a great pet sitter!

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Neysa S.
Sitter Profile Image: Zackary T.
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Zackary T.
from
$31
per night
5.0 out of 5 stars
14 reviews
5 repeat clients
7 years of experience
Edgerton, WI, 53534

Zackary was so awesome! We was super communicative and seemed to spend a lot of time at home with our two kitties boys. He asked questions when needed, checked in often and sent cute pictures! Our kitties were definitely happy when we got home and he was respectful of our space. Thank you so much Zack, the boys will be happy to see you in the future 😊

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Jordalyn S.
Sitter Profile Image: Phillip W.
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Phillip W.
from
$70
per night
5.0 out of 5 stars
22 reviews
8 repeat clients
23 years of experience
Stoughton, WI, 53589

I can’t say enough good things about working with Phillip! He was kind, professional, and easy to trust with our two hyper and reactive doggos. Above all, it was such a relief to know that our fur babies were being cared for by someone who loved dogs as much as we do!!! We simply relaxed and enjoy our vacation! Thank you, Phillip!

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Gail G.
Sitter Profile Image: Ian M.
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Ian M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
21 reviews
5 repeat clients
4 years of experience
Janesville, WI, 53546

Ian was an absolute life saver! After another person backed out less than 48 hours before my husband and I were scheduled to leave town for several days, Ian answered my last minute request, and saved the day! He came to meet us and our dog the same evening as the request, and immediately established a rapport with our dog. While we were gone, he kept us updated on how things were going, and was very responsive to requests. I would love to have Ian stay with our dog again, and would highly recommend him to anyone!

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Meredyth P.
Sitter Profile Image: Talia W.
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Talia W.
from
$28
per night
4.8 out of 5 stars
6 reviews
2 repeat clients
11 years of experience
McFarland, WI, 53558

Talia did a great job sitting for my dog Koko and she was very responsive in her messaging replies

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Kyle C.
Sitter Profile Image: Kelsea & Astasia L.
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Kelsea & Astasia L.
from
$28
per night
15 years of experience
Stoughton, WI, 53589

About: I've always grown up living around pets and animals of any kind, grew up with farm animals and household pets, lots of experience with both large and small dogs, and plenty of experience with cats. I currently have 3 cats at my home, and I love spending time with dogs as well. I've worked with both young and old cats and dogs as well! I also have experience with disabled pets (one of my dogs was a rescue that lost a leg in an accident). My partner works full time as a manager at a local pizza place in Stoughton, so they might come and go a bit for work, but I work from home and am able to stay in the home with your animals when and as needed. I work from home as a digital artist, so my schedule is completely open and flexible, and I can fit in pet care at any time that might be needed. I am very open to working around any specific care needs your fur family might need, and can work around your wants and needs for your pets care in and out of your home!

Sitter Profile Image: JESSICA P.
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JESSICA P.
from
$45
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
20 years of experience
Edgerton, WI, 53534

Jessica has stayed with our 2 girls Nala and Frida twice now . They warmed up to her quickly . Jessica sends photos and updates a couple times a day. She even brought them little gifts the 2nd time coming . Jessica is very kind and has been

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Marcie R.
Sitter Profile Image: Mallory N.
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Mallory N.
from
$50
per night
4.8 out of 5 stars
23 reviews
2 repeat clients
7 years of experience
Lake Mills, WI, 53551

Mallory took great care of both of our dogs, especially our medically needy senior. She was easy to communicate with and diligently monitored symptoms in our senior. Our dogs were well cared for and I would happily rebook.

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Allison D.
Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$55
per night
5.0 out of 5 stars
48 reviews
15 repeat clients
30 years of experience
Brentwood Village, Madison, WI, 53704

I cannot say enough good things about our experience with Elizabeth. She was so diligent about following Gus's routine, so great about keeping us updated on how things were going, and above all SO kind and understanding of our pups needs as a spicy/reactive dog. She left me completely at ease and able to relax on our trip. I am so glad we've found her and that our baby has someone he will not just be comfortable with, but excited to spend time with while we are gone!

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Mya E.
Sitter Profile Image: Emma W.
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Emma W.
from
$45
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
5 years of experience
Cottage Grove, WI, 53527

Emma was absolutely fantastic with our large dogs! They are a bit high maintenance in their own ways but they were taken care of perfectly! Will absolutely be booking again in the future!

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Young A.
Sitter Profile Image: Ava N.
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Ava N.
from
$45
per night
5.0 out of 5 stars
2 reviews
10 years of experience
Stoughton, WI, 53589

Ava was wonderful! Great communication and was so incredibly helpful when we needed a cat sitter last minute. Our shy cat warmed up to her right away. Will definitely book her again.

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Julie W.
Sitter Profile Image: Tucker S.
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Tucker S.
from
$42
per night
5.0 out of 5 stars
8 reviews
10 years of experience
Orchard Ridge Community, Madison, WI, 53711

Tucker did a great job watching Zoe & Mocha - regularly sent photos, provided updates from each visit, and was very communicative in providing care.

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Eric L.
Sitter Profile Image: Emma R.
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Emma R.
from
$35
per night
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Sun Prairie, WI, 53590

Emma did a great job watching my dogs and my house while I was gone.

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Rita B.
Sitter Profile Image: Danielle L.
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Danielle L.
from
$45
per night
5.0 out of 5 stars
23 reviews
6 repeat clients
12 years of experience
Janesville, WI, 53548

Danielle was wonderful with my pups! Along with TLC, she was able to handle their challenges and keep them happy and healthy. I loved the pics she sent and immediately responded to any check-ins or just my missing them and needed to see a picture right now!

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Bebe B.
Sitter Profile Image: Karina M.
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Karina M.
from
$45
per night
5.0 out of 5 stars
26 reviews
6 repeat clients
5 years of experience
Marquette, Madison, WI, 53703

Karina did a wonderful job looking after our cat for a long weekend. We came back to a relaxed cat and a house in perfect order. Thanks, Karina!

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Chloe H.
Sitter Profile Image: Sandina P.
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Sandina P.
from
$40
per night
5.0 out of 5 stars
28 reviews
5 repeat clients
28 years of experience
Fort Atkinson, WI, 53538

First time using Sandina and Riley did very well under her watch. 3 pictures. Will definutely use her again.

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Linda L.
Sitter Profile Image: Shatoria W.
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Shatoria W.
Star Sitter
from
$68
per night
5.0 out of 5 stars
33 reviews
11 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Shatoria was great. She engaged my two pups quite a bit. I received lots of photos of happy dogs, some cuddling with her - a good sign! The house was in excellent order, just as I left it. I plan to invite her to house/dog sit again. Thanks Shatoria!

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Marit S.
Sitter Profile Image: Morgan L.
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Morgan L.
from
$30
per night
8 years of experience
Edgerton, WI, 53534

About: I bring hands-on experience caring for dogs with a variety of needs, from energetic pups to seniors requiring extra attention. I’ve successfully cared for up to three dogs at a time, making sure each one gets individual love, exercise, and attention. I’m also comfortable providing medications—whether it’s oral medicine or ear treatments—so you can feel confident your pet’s health routines will be followed with care. My goal is always to make your dog feel safe, happy, and loved while giving you peace of mind knowing they’re in capable hands. As a full-time teacher, my weekdays are structured and reliable—which means your pets can count on a consistent routine with me, too! I’m available for drop-ins and walks before and after school hours, and I have every other weekend off, which allows me to dedicate extra time to longer visits, boarding, or overnight care. Teaching has given me patience, attentiveness, and strong multitasking skills—all qualities I bring into pet care. I also offer house sitting, which means your pets can stay in the comfort of their own home while I keep up with their routines and give them lots of love and attention. I make sure your pets feel safe, your home is cared for, and you have peace of mind while you’re away. Spending time with animals is truly one of the best parts of my week! When I’m caring for a dog in your home, I want them to feel completely loved and comfortable while you’re away. I do my best to stick to their normal routine—whether that’s mealtime, walks, playtime, or even just those quiet snuggle moments they look forward to. I pay close attention to the little things that make your dog happy, because I know how much they mean to you. While I’m there, I also treat your home with the same care and respect I’d want for my own. You can count on me to keep things tidy and follow your instructions so you can come back to both a happy pup and a peaceful home. My goal is always to make your dog feel like they’re spending time with a trusted friend until you return.

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

Book with peace of mind

  • 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.

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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Hillside

Select a filter and find qualifying sitters offering house sitting.

Sitters in Hillside average 4
repeat house sitting clients

FAQs for House Sitting - Hillside

Frequently asked questions about Rover

As of July 2026, there are 975 sitters on Rover offering House Sitting across Hillside. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Hillside walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Hillside maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Hillside choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Hillside. On Rover:

  • 96% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 96% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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