House Sitting in Silver Spring, 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.

Search Results

Confirmed availability: Memorial Day
Cindy T.
1.
TOTAL DOG LOVER :)Wauwatosa, WI, 53222
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Cindy was great to work with and very flexible with scheduling. We received text messages with photos and updates while we were away. We will be using her servi… (more)

from
$35
per night
Kim M.
2.
Kim 
Verified Enhanced Background Check
Fenced yard and lots of love!Timmerman West, MILWAUKEE, WI, 53225
Dog Boarding

I could not have asked for better sitters than Kim and Joe. They took such great care of our dog Bonnie and sent updates to let us know how she was doing. Their… (more)

from
$27
per night
Confirmed availability: Memorial Day
Kadijah L.
I’m a dog lover! ?Lincoln Creek, Milwaukee, WI, 53216
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Kadijah was great! Would definitely feel comfortable having her board my dog again and would recommend her to any friends or family that needed a dog boarded. … (more)

from
$60
per night
Calendar Recently Updated
Angela K.
4.
We’ll Keep Their Tail WagginMenomonee Falls, WI, 53051
Dog Boarding, Drop-In Visits, Doggy Day Care

This was our first time using Rover and we are very pleased with Angela. She sent us pictures of Max and updates which made us feel at ease. Max had a great tim… (more)

from
$35
per night
Calendar Recently Updated
Rebecca & Bobby M.
Two for one love!Brookfield, WI, 53005
Dog Boarding

Rebecca and Bobby took great care of my little anxious Peekapom. Rebecca did a great job of slowly introducing herself and her dog to Peeka. Peeka did great and… (more)

from
$50
per night
Confirmed availability: Memorial Day
For the Love of the Dog-WI™Pheasant Run, Milwaukee, WI, 53224
Dog Boarding

Michelle was more than flexible with everything that came our way. Our vacation started with our dog getting sick from eating something and she was more than wi… (more)

from
$38
per night
Calendar Recently Updated
7.
Multiple walks and cuddles!Washington Heights, Milwaukee, WI, 53208
Dog Boarding, Doggy Day Care

My pup Walter always comes home from Deann happy and tired from playing with the other dogs! Deann is so flexible and easy to work with. I really appreciated th… (more)

from
$35
per night
Confirmed availability: Memorial Day
8.
Wee looove the fur babies ♥️Kops Park, Milwaukee, WI, 53222
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Yisel was absolutely wonderful! Lots of updates and it was obvious our dog had a great time! (more)

from
$40
per night
9.
Love to walk and cuddle.Whitefish Bay, WI, 53217
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Rhonda was amazing! She would send my wife and I daily updates of her and Bella's adventures. When we pulled up to Rhonda's house, Bella was chilling on her lap… (more)

from
$30
per night
Calendar Recently Updated
10.
Accommodating, responsible, lovingKops Park, MILWAUKEE, WI, 53222
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Sara was such a great choice for my dog. It was very late notice but she really came through and took great care of Bubba. She updated me multiple times during … (more)

from
$34
per night
11.
I Absolutely Love Fur Babies ❤️❤️Hampton Heights, Mikeaukee, WI, 53218
Dog Boarding
14 years of experience

About: I’ve known how to care and create bonds with animals at a very young age. I’m 34 and we’ll seasoned with pets of all ages. I really enjoy the persona… (more)

from
$60
per night
We’ll meet your dog's needs!Grasslyn Manor, Milwaukee, WI, 53216
Dog Boarding, Drop-In Visits, Dog Walking

Elizabeth and her family are awesome. She took excellent care of Lovey and kept me updated with daily pictures and messages. I would rebook without hesistatio… (more)

from
$32
per night
Calendar Recently Updated
13.
Dog lover work from homeWest Allis, WI, 53214
Dog Boarding, Doggy Day Care

It was our dogs first time away from us for a whole week!!! I was very nervous, but Jill was amazing! Send me pictures and kept me updated! Definitely recommend… (more)

from
$45
per night
Calendar Recently Updated
14.
Fenced in yard with homemade treatsMenomonee Falls, WI, 53051
Dog Boarding

Jayce had an amazing time spending four days with April, Lupo and Niko. It was our first time using Rover and April made it an awesome experience! Very communic… (more)

from
$35
per night
Calendar Recently Updated
15.
Jen 
Verified Background Check
Unoffended by slobber & muddy pawsEnderis Park, Milwaukee, WI, 53210
Dog Boarding, Doggy Day Care

Jen was an amazing sitter for my chug Izzy! She was patient with my somewhat shy dog, who quickly grew close with the family. Thank you again! We’ll be in touch… (more)

from
$27
per night
Confirmed availability: Memorial Day
16.
Lover of all pets!Mount Mary, Milwaukee, WI, 53222
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Kayla was excellent all around from the first introduction to the final drop off. She has a great backyard and Otis loved playing with her two dogs. This was … (more)

from
$45
per night
Calendar Recently Updated
Open and flexible dog attendeeKilbourn Town, 53233, WI, 53233
Dog Boarding, Doggy Day Care, Dog Walking

Isabella was amazing! She help us out with taking care of our little pup Bigos on last minute request. She was very flexible and easy to communicate and Bigos w… (more)

from
$35
per night
Calendar Recently Updated
18.
I love dogs they are family.menomonee falls, WI, 53051
Dog Boarding, Doggy Day Care

Kathy was great with our sweet little George. She sent updates and adorable pictures of his stay everyday. George came home very relaxed and happy. This was a g… (more)

from
$25
per night
Calendar Recently Updated
19.
I enjoy dogs and they like it here.Menomonee Falls, WI, 53051
Dog Boarding, Doggy Day Care

Randy was a "pawsome" host to our two large pups! We have a Great Dane and a greyhound and they loved it at Randy's! He has a huge fenced in yard that the dogs … (more)

from
$35
per night
Confirmed availability: Memorial Day
20.
We can’t wait to meet your pup!Wauwatosa, WI, 53222
Dog Boarding, Drop-In Visits, Doggy Day Care

Sarah took our girls in very last minute for an over night stay and they had a great time, both came back tired from playing! She sent pics and kept us updated … (more)

from
$30
per night

Dog owners in Silver Spring, 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 Silver Spring.

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 Silver Spring 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 Silver Spring, 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 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 Silver Spring, 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: