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.
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Travis H.
1.
Love & Exercise for your dog or catMartin Drive, Milwaukee, WI, 53208
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Travis did a great job. He communicated well throughout the entire process and was easy to work with. He provided photos and updates throughout the 3 days he … (more)

from
$40
per night
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Sarah P.
2.
Dogs and cats = girl's best friendsBrookfield, WI, 53005
House Sitting, Drop-In Visits, Dog Walking

Sarah was amazing! She met with us and our pets beforehand, she was easy to keep in contact with, and she sent us pictures of the pets along with updates while … (more)

from
$35
per night
Confirmed availability: Memorial day
Teresa O.
3.
Your Pet’s NannyMenomonee Falls, WI, 53051
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Teresa is always very caring and attentive to our 14 year old little maltese. She comes to our home to watch our little fur baby. I highly recommend her. (more)

from
$40
per night
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Meg M.
4.
Meg 
Verified Background Check
I love to walk and play with dogsAvenues West, Milwaukee, WI, 53233
House Sitting, Drop-In Visits, Dog Walking

Meg has frequently taken care of my two dogs and one cat. She is responsible and loving while caring for my pets. Meg has proven to be dependable, timely and … (more)

from
$35
per night
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Rachel H.
5.
** Mission: meet ALL the dogs **Lower East Side, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking

Rachel was absolutely amazing! She was really great at communicating and sending lots of pictures throughout the stay. Most notably, she went above and beyond t… (more)

from
$27
per night
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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
$30
per night
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7.
The Friendly, Neighborhood Pet LadyBrown Deer, WI, 53223
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jax was phenomenal! Our pup can be a handful at times and she handled him so well. She took the time to not only take him out but to play with him and get him t… (more)

from
$35
per night
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8.
Experienced Animal Caretaker! 😻Brookfield, WI, 53005
House Sitting, Drop-In Visits, Dog Walking

Taylor was great, she came out several days before her appointed time to sit for a meet and greet, she was friendly and obviously loves animals, after the meet… (more)

from
$40
per night
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9.
I <3 furry friends & miss my fam’sLower East Side, Milwaukee, WI, 53202
Dog Boarding, House Sitting

Talor was amazing!!! Super responsive, personable, and made sure to send photo updates each day we were away. She was very attentive to our dog and made sure he… (more)

from
$30
per night
Confirmed availability: Memorial day
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
$40
per night
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11.
🐾 Reliable,Caring Flexible 😸🐕Northridge Lakes, Milwaukee, WI, 53223
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sharon did a wonderful job of caring for our pets, and keeping an eye on the house for the weekend. Communication was good, and Gus our goldendoodle and Murdoc… (more)

from
$38
per night
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12.
Pawesome, Detail-Oriented SitterCambridge Heights, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

We needed a house sitter for our two pups and our cat, and we were beyond happy with Kaitlyn! This was our first time leaving our pets for an extended time, and… (more)

from
$35
per night
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13.
Dogs are the joy of my life!Glendale, WI, 53217
House Sitting, Drop-In Visits, Dog Walking

I loved her service. I would recommend her to anyone (more)

from
$40
per night
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Dog Loving Couple!Wauwatosa, WI, 53225
Dog Boarding, House Sitting

Vince is a responsible, caring individual with two of his own pups at home. He is very knowledgeable in regards to dog care/training and would be a wonderful ca… (more)

from
$38
per night
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15.
I’m the fairy dog mother.Harambee, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

About: Hi, my name is Kaliyah & I am 20 years old. I am a high school graduate, soon to be professional dog groomer. I don’t have much professional experie… (more)

from
$50
per night
Confirmed availability: Memorial day
16.
Jan 
Verified Background Check
I am a pet lover; home full timeWhitefish Bay, WI, 53217
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jan watched my dog 2 weekends in a row. Sadie loved her company. Jan is the sweetest lady ever and always sent me periodic updates on how Sadie was doing. I wou… (more)

from
$70
per night
Confirmed availability: Memorial day
17.
True compassion for all animalsWauwatosa, WI, 53213
House Sitting, Drop-In Visits, Dog Walking

My dog loves Gina more than my dog loves me.....Gina is simply wonderful with the care of my 5 year old Golden. (more)

from
$40
per night
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Make new dog friends!Mount Mary, Milwaukee, WI, 53222
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Jonathan was available to come to my house over the holiday weekend on short notice, despite having plans of his own. He was super reliable and easy to work wit… (more)

from
$35
per night
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19.
Tell Your Dog I Said "Hi"......Glendale, WI, 53209
House Sitting, Drop-In Visits, Dog Walking

Becky is an absolute dream sitter! She sent so many photos, tons of updates, asked thoughtful questions and even offered some super great advice! She’ll be ou… (more)

from
$45
per night
Confirmed availability: Memorial day
20.
I’m a dog lover! ?Timmerman West, Milwaukee, WI, 53225
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I am a dog lover! I will take car of your pet as if it was mines! I have a lot of love and pet experience that I would love to share with your family… (more)

from
$25
per night

Rover also offers House Sitting in:

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: