House Sitting in Hillside, Milwaukee

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Blythe R.
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Sitter Profile Image: Blythe R.
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1.

Blythe R.

Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
4.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
137 reviews
61 repeat clients
from
$55
per night

We can’t say enough good things here. We had a really bad boarding experience and needed to do something different. We were a little hesitant with having someone in our home but Blythe was awesome. We have a large dog who is pretty needy and a little old man. She took pics, gave us updates and did everything we asked and our home looked the exact way we left it. Would highly recommend!

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Sitter Profile Image: Carole & Shannon C.
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Sitter Profile Image: Carole & Shannon C.
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2.

Carole & Shannon C.

east side dog-whisperers
Murray Hill, Milwaukee, WI, 53211
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 reviews
15 repeat clients
from
$60
per night

Carole was nothing short of amazing! I have 2 senior dogs, one of whom is very “particular” as far as the people she likes. Carole was able to walk her and care for her without any issues. I received photos and updates and felt completely at ease knowing that they were in good hands.

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Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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3.

Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
4.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
77 reviews
22 repeat clients
from
$27
per night

Rachel is honestly the *best* - Arya loved spending the weekend with her and she left the house spotless!! We are so grateful we found her and can’t recommend her enough :) thank you Rachel!!

Sitter Profile Image: Daniela & Michael P.
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Sitter Profile Image: Daniela & Michael P.
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4.

Daniela & Michael P.

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
279 reviews
161 repeat clients
from
$65
per night

Excellent job!! I have two large dogs and a cat, who can be a handful. They took great care of them all. Sent me daily updates with pictures. They allowed me to travel without worrying about my pack. I already have booked them for another trip, and will use them going forward.

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Sitter Profile Image: Cindy H.
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Sitter Profile Image: Cindy H.
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5.

Cindy H.

Reincarnated Dog Here!
wauwatosa, WI, 53213
3.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
28 reviews
6 repeat clients
from
$65
per night

Cindy never fails to please! I was able to leave my dog Daisy with her while we attended a wedding. Cindy sent lots of pictures, and it was clear that Daisy was getting along well with her little pups! Daisy is an older dog, and easily becomes stressed and anxious. At home, she becomes distressed if she awakes and I am not in the room. When I went to pick her up at Cindy's, she looked as though she was feeling totally safe and secure right where she was! It warms my heart to see her so content.

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Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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6.

Jessica Z.

Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
85 reviews
29 repeat clients
from
$59
per night

Jessica was amazing!! She sent photos and kept the lines of communication open with us throughout our trip. We came home to a clean house and happy pets. We will definitely be using her services for house sitting with our babies again!!

Confirmed availability: Easter Weekend
Sitter Profile Image: Abby C.
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Sitter Profile Image: Abby C.
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7.

Abby C.

Obsessed cat mom & foster cat mom
Lower East Side, Milwaukee, WI, 53202
1.0 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
31 reviews
5 repeat clients
from
$25
per night

Abby has taken care of my dog and cats on numerous occasions. She was responsible and gave my pets extra attention. I always knew they were well cared for when Abby was the pet sitter. Her love for cats is apparent and she will treat yours like her own.

Sitter Profile Image: Payton R.
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Sitter Profile Image: Payton R.
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8.

Payton R.

making tails wag one walk at a time
Milwaukee, WI, 53211
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$40
per night

Payton did a great job staying with my little girl, Malena. She sent photos and updates and probably spoiled Malena so much that she just said 'oh it's you' when I came home :) I'd love to have Payton sit again.

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Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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9.

Leandrea R.

Rover 101
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
2.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
99 reviews
36 repeat clients
from
$60
per night

Leandra did an amazing dog sitting at our house. She provided lots of updates and pictures that made us feel so comfortable and confident that our doggo was getting the best care and love.

Sitter Profile Image: Beth P.
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Sitter Profile Image: Beth P.
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10.

Beth P.

Summer/weekend house sitting
Milwaukee, WI, 53212
1.5 mi. away
House Sitting
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$60
per night

Beth is a Godsend! She stayed at our home for five days and took exceptional care of our many animals: our dog, cats, rabbits, Guinea pig and fish. We came back to a tidy house and relaxed animals. She took our dog on two mile walks and sent photos and updates regularly. We couldn’t have asked for a better sitter. She is kind and considerate. We highly recommend Beth!

Sitter Profile Image: Micaela B.
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Sitter Profile Image: Micaela B.
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11.

Micaela B.

Pet lover looking for new friends!
Riverwest, Milwaukee, WI, 53212
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
29 reviews
7 repeat clients
from
$50
per night

Micaela put us at ease when my husband & I left our dog with someone other than family for the first time. She sent regular updates & her communication was wonderful overall. Would absolutely book Micaela again.

Sitter Profile Image: Jordanne H.
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Sitter Profile Image: Jordanne H.
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12.

Jordanne H.

I’m a teacher with all summer off!!
Riverwest, Milwaukee, WI, 53212
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
5 repeat clients
from
$50
per night

Jordanne was absolutely incredible. She was prompt and an excellent communicator. She took excellent care of my pup and kept my apartment clean. I highly recommend and will use Jordanne again in the future.

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Sitter Profile Image: Riley N.
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Sitter Profile Image: Riley N.
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13.

Riley N.

Animal lover since birth! PETS=FAM
Milwaukee, WI, 53212
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
1 repeat client
from
$60
per night

Riley was great with our little anxious dogs. They immediately loved her and seemed very content when we got home! We’ll definitely book with her again!!

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Sitter Profile Image: Jackie C.
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Sitter Profile Image: Jackie C.
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14.

Jackie C.

Looking forward to meet your pet!
Brewer's Hill, Milwaukee, WI, 53212
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
53 reviews
20 repeat clients
from
$70
per night

Jackie is incredible! Great communication, she is punctual, sent so many pictures, and best part was my pup was so happy. I definitely recommend! Thanks again Jackie!!

Confirmed availability: Easter Weekend
Sitter Profile Image: Danielle A.
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Sitter Profile Image: Danielle A.
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15.

Danielle A.

Flexible, professional pet care
Upper East Side, Milwaukee, WI, 53211
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
42 reviews
12 repeat clients
from
$75
per night

Danielle was fantastic. She watched over my 2 bulldogs over Memorial Day weekend and was fantastic. She kept us updated with notes and pictures, and asked all the right questions to truly understand both boys. Would recommend again!

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Sitter Profile Image: Kassidy O.
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Sitter Profile Image: Kassidy O.
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16.

Kassidy O.

Animal lover & flexible schedule
Lower East Side, Milwaukee, WI, 53202
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
2 repeat clients
from
$28
per night

Kassidy was very respectful of our home and was so good with our dogs. She shared pictures, communicated regularly, and gave them lots of love. Would recommend!

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Sitter Profile Image: Emma K.
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Sitter Profile Image: Emma K.
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17.

Emma K.

Animals bring joy to my life!
Milwaukee, WI, 53202
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
3 repeat clients
from
$30
per night

Emma is always great with Princess! I know I can rely on her to take care of my senior girl and her special needs. Thanks Emma! ?

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Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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18.

Erica L.

Rover 101
Pro. Dog Handler with WFH job!
Park West, Milwaukee, WI, 53206
1.8 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
77 reviews
28 repeat clients
from
$65
per night

Erica came to house sit our 5 month old dachshund. It was our first time leaving him and she made us feel comfortable he would be in great hands. She came over prior for a meet and greet and wrote down all the crazy notes i had for her. My dachshund is really teething/nipping and she went and got him puppy teething bones and Truly went above and beyond (also providing new dog parents with helpful puppy training tips)! She sent many pictures of our pup throughout the week and left our apt perfectly clean. We can’t wait to have Erica dog sit again!

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Sitter Profile Image: Jennifer T.
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Sitter Profile Image: Jennifer T.
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19.

Jennifer T.

Your dogs second best friend.
Milwaukee, WI, 53212
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
104 reviews
33 repeat clients
from
$45
per night

This was my first time utilizing Rover and I can't say enough good things about Jennifer! She recently provided 5 days in-home services for my 9.5 year old dog and 14 y.o. cat. Both are pretty chill but do require medications and LOTS of attention and Jennifer provided both. She was reliable, transparent with her schedule and sent lots of updates and pictures, minimizing the stress associated with leaving our fur babies with others. Would highly recommend.

Sitter Profile Image: Maggie P.
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Sitter Profile Image: Maggie P.
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20.

Maggie P.

Will love your pet like my own :)
Riverwest, Milwaukee, WI, 53221
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
13 repeat clients
from
$50
per night

We were delighted to have Maggie housesit with Connor. Everything was thorough and efficient with his med schedule, and she is very experienced which we appreciated. We would definitely recommend Maggie to others, as well as have her back again ourselves.

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Rover also offers House Sitting in these neighborhoods:

Rover also offers other services in Hillside:

Pet parents in Hillside, Milwaukee, WI love dog sitters on Rover.com. 1089 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:

House Sitting