House Sitting in Hillside, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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Alicia S.
1.
Trustworthy, Loving, Genuine, SillyMurray Hill, Milwaukee, WI, 53211
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Alicia is fantastic! She did an excellent job caring for our pets, was respectful of our home & was open and transparent in communication. Alicia was incredibly… (more)

from
$100
per night
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Marina M.
2.
You deserve a worry free getaway!Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

We asked Marina to come in at the last minute to watch our 14 year old dog for a couple of days. She was prompt and asked some great questions. While we were aw… (more)

from
$65
per night
Elaine B.
3.
Caring & trustworthy pet sitter 🥰MILWAUKEE, WI, 53211
House Sitting

If I give more than 5 I would. By far the best pet sitter I’ve had. Bubbly personality and attentive to my puppies needs. Very great communication and even … (more)

from
$30
per night
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Dominique L.
Flexible and willing to travel!Murray Hill, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Dominique provided a wonderful service while I was away. House sitting as well as care for my Tinker I was happy with the care they received. Will definitely … (more)

from
$37
per night
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Malissa N.
Specialized in House/Dog SittingUpper East Side, Milwaukee, WI, 53211
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Couldn’t ask for a better sitter. She takes care of our dogs with all the care and love youd hope for . You can just tell the dogs are happy when we get back ho… (more)

from
$60
per night
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6.
EMOTIONAL SUPPORT HUMANRiverwest, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Jabril was a most excellent caretaker for our fur babies. Highly recommend! Sophie, our big Catahoula mix, and Ollie our black cat, took to Jabril like family. … (more)

from
$45
per night
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7.
Happiness is with your furry friendMurray Hill, Milwaukee, WI, 53211
House Sitting, Drop-In Visits

Chloe is amazing!! We had a lovely week in Cancun and didn’t have to worry about our sweet pup. She kept him company and took him on many walks + took care of o… (more)

from
$44
per night
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8.
Can't Wait to Meet Your Fur Baby!Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Ameera was great at communicating and sending pictures of our furry friends without even asking. She exercised them often and gave them the attention they neede… (more)

from
$70
per night
9.
Experienced, reliable, retired!!!!!Historic Third Ward, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Laurie was so great with our puppy! I asked her very last minute too, she was very accommodating and send photo updates. Lovely lady, would definitely recommend… (more)

from
$65
per night
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10.
A dog lover who loves the outdoors!Lower East Side, Milwaukee, WI, 53202
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Molly is a great person, and she has always been so sweet and patient around my shy rescue dog. I have seen her love for her own dogs, and I know with her carin… (more)

from
$35
per night
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11.
I <3 furry friends & miss my fam’sLower East Side, Milwaukee, WI, 53202
Dog Boarding, House Sitting

Talor was attentive and responsive. She was great about communicating and kept our pup happy. I would definitely go with Talor again the next time I'm out of to… (more)

from
$85
per night
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12.
Loving sitter, enthusiastic walkerRiverwest, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Jessica was terrific! My 2 cats who really don’t like to be left alone,(ie: hold a grudge and snub me) behaved as if I had not left them! Not much more to say! (more)

from
$40
per night
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13.
Dog Buddy & Reliable CareMilwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Karsyn was great with Zoe from start to finish! She was very welcoming, which made leaving Zoe with confidence that she was being taken care of, very easy! Kars… (more)

from
$35
per night
14.
Sweet animal loverJuneau Town, Milwaukee, WI, 53202
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Dominique and Clay are incredible. Our dogs loved them and they made me feel so relieved to have them at our home with the dogs while we were out of town. They’… (more)

from
$45
per night
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Your dogs second best friend.Riverwest, Milwaukee, WI, 53212
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

When Jennifer came to meet us Mini ran up and couldn't stop wagging her tail - Mini loves meeting new people but it's like she knew Jennifer was a dog person, I… (more)

from
$45
per night
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16.
Neighbor providing additional loveJuneau Town, milwaukee, WI, 53202
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Awesome job! Would highly recommend. Expert care of our needy, elderly Great Pyrenees, and pure wizardry with our little shepherd who can be tricky unless you’r… (more)

from
$38
per night
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17.
Friendly, Careful, and Loving!Juneau Town, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Tiana grew up in a home of dedicated dog/cat and horse lovers! She is an attentive and caring person, who truly loves and admires animals of all kinds (except … (more)

from
$30
per night
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18.
Your Pets are my Passion!Juneau Town, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

I booked Hailey at the last minute to house sit and to sit for my dog and she did such an amazing job!!! She sent me pictures and communicated with me daily whi… (more)

from
$50
per night
19.
Enamoured with pups of all sortsRiverwest, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Kristen did a wonderful job with our 2 geriatric pugs who have some special needs. While we were away, she sent pictures and updates. When we came home, they we… (more)

from
$125
per night
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20.
Ali 
Verified Background Check
Trustworthy, friendly and punctualLower East Side, Milwaukee, WI, 53202
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Ali is an amazing and caring person who is an avid dog lover. She truly cares for each dog as if it were her own. She is extremely energetic, athletic and activ… (more)

from
$40
per night

Pet parents in Hillside, Milwaukee, WI love dog sitters on Rover.com. 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Hillside house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Hillside, Milwaukee, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Hillside house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Hillside, Milwaukee donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Milwaukee.

We're proud to support over 200 organizations across the nation, including: