House Sitting in Williamsburg, 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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Dominique L.
Flexible and willing to travel!Murray Hill, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Dominique was wonderful to our somewhat difficult dog. She was patient and made sure our dog was well taken care of when we were out of town. (more)

from
$37
per night
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Jessica Z.
Loving sitter, enthusiastic walkerRiverwest, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Jessica’s interest in taking care of, and indeed becoming friends with, all animals is extraordinary. I know cats and dogs have the ability to sense human emoti… (more)

from
$40
per night
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Alicia S.
3.
Trustworthy, Loving, Genuine, SillyMurray Hill, Milwaukee, WI, 53211
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
$115
per night
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Chloe V.
4.
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
Confirmed availability: 4th of July
Marina M.
5.
You deserve a worry free getaway!Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Marina was AMAZING. Highly highly recommend. The frequent pictures and updates were great, our house looked like nobody was even there, and the animals were sup… (more)

from
$65
per night
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6.
Beagle owner & dog loverDowner Woods, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking

Pamela is a wonderful, loving, caring pet owner herself. She is fantastic with any and all pet breeds and types. Your pet will get endless pets and love from Pa… (more)

from
$35
per night
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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
$65
per night
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8.
Ready for a puur-fect getaway? 🦮🐱Riverwest, Milwaukee, WI, 53212
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sarah has cared for my small dog Stella before. My dog ended up loving her, and barely wanted to leave her place. I recommend her to any pet owner that needs a … (more)

from
$30
per night
9.
Caring & trustworthy pet sitter 🥰MILWAUKEE, WI, 53211
House Sitting

Elaine was very knowledgeable and experienced with dog care. She gave updates and photos during her stay. Wanda was a calm puppy when we got home, which tells… (more)

from
$30
per night
Confirmed availability: 4th of July
10.
Can't Wait to Meet Your Fur Baby!Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Ameera was AMAZING. This was our first experience with Rover and leaving our puppers with someone new and Ameera did awesome at keeping us updated throughout th… (more)

from
$70
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 is an amazing human that really cares about the dogs she sits for and the people she is helping out. She rescued us when our previous dog sitter failed to… (more)

from
$95
per night
Confirmed availability: 4th of July
12.
The right sitter FUR you ♥️Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits

Shabana stayed in our home with our 2 large dogs for 6 nights while we were on vacation and she did amazing! She gave us updates and pictures every day. One of … (more)

from
$42
per night
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13.
Rio 
Verified Background Check
caring & reliable sitterRiverwest, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Rio went above and beyond! Very good communication and plenty of pictures were sent. We trust Rio completely with our animals and our home. We will definitely b… (more)

from
$30
per night
Confirmed availability: 4th of July
14.
Leave your pet in good hands!Murray Hill, Milwaukee, WI, 53211
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sierra did a wonderful job with Louie while we were out of town! We got daily updates, but not overwhelming. She took him to the dog park, went on walks and ov… (more)

from
$60
per night
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15.
Will spoil your dog as my own!Riverwest, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Paige was excellent! She was kind, always kept me updated, and took amazing care of my senior dog. I was worried about leaving him with a sitter as he can be re… (more)

from
$38
per night
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16.
Snuggles, Walks and TreatsWhitefish Bay, WI, 53211
House Sitting, Drop-In Visits, Dog Walking

Colleen was absolutely fantastic and took all of the stress out of leaving our dog behind while going on vacation. Usually he’s left with family and when we ret… (more)

from
$50
per night
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17.
Active outdoorsy animal loverUpper East Side, Milwaukee, WI, 53211
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
6 years of experience

About: I’ve taken care of my sister and neighbors throughout the past 6 years. My sister has a very sweet pit bull that I’ve given full care to. I’ve washed… (more)

from
$60
per night
18.
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
Confirmed availability: 4th of July
Your dogs second best friend.Riverwest, Milwaukee, WI, 53212
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jennifer was awesome! Super responsive, personable, and made sure to send picture updates of our happy pup. We had her stay in our house while we were gone and … (more)

from
$45
per night
Calendar Recently Updated
20.
Loving to all pups❤️Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking

Annie has had dogs her entire life and she currently has her own dog that she raised and cares for herself. She is a true animal lover and is very responsible … (more)

from
$45
per night

Dog owners in Williamsburg, Milwaukee, WI love booking house sitting with sitters on Rover.com. Over 1,089 pet owners have reviewed house sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking house sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book house sitting with Rover? Check out our average house sitting rates to get an idea before reaching out and starting a conversation with a house sitter near you in Williamsburg.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Williamsburg house sitter in seconds on Rover.com. If you're looking for trusted dog sitters while you're away, whether it's for one night or a whole month, you can find a house sitter in Williamsburg, Milwaukee, WI who meets your and your dog's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your dog, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of dog lovers pet sitters and dog walkers.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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 Williamsburg, 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: