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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Confirmed New Years Availability
1. Lindsey

Fur mama and dedicated dog lover

Saint Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Lindsey Did a great job. This was our first visit and the dogs were a little anxious. Lindsey did a great job and was very patient with my dogs little idio... (more)"

2. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Sarah is amazing. She was so great with my puppy, sent me photos while I was away, very accommodating to my schedule, would definitely recommend to anybody w... (more)"

3. Diana

Ready to go, rain or shine!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Diana has been so helpful with Murphy! I've used her a bunch of times and Murphy just adores her. Diana is really communicative and sweet, she is highly depe... (more)"

4. Emma

I would love to run with your dog!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Emma was professional, and very caring. I love that she sent us photo updates of our pets and that she was very responsive. (more)"

5. Yessenia

Home full-time- Years of experience

Riverwest, Milwaukee, WI, 53212

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

2 repeat clients

"Yessina was very reliable, caring , and thoughtful and sent lots of updates and pics and was always expressing how much she loves my dogs. I would definitely... (more)"

6. Lizzi

Dog's Best Friend

Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

11 repeat clients

"Lizzi is great! We have a big lab/pit mix and he's very energetic. Lizzi was able to calm him down in record time. She's very responsive and great. We are go... (more)"

7. Hannah

Working part time, love walks

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Hannah did a great job watching a menagerie while house sitting for me. My two pups loved being able to stay home, snuggle in bed, and go about their usual ... (more)"

8. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

19 repeat clients

"Sandy was terrific with my dog who suffers from separation anxiety. Buff typically stops eating for 2 - 3 days when I am away and then it takes her several d... (more)"

Available this weekend
9. Taylor

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Taylor is great! She is super professional, but will give your four-legged family member all the love and attention it needs. I highly recommend using Taylor... (more)"

10. Ashlyn

I'll exceed your pet's needs

Northpoint, Milwaukee, WI, 53211

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Ashlyn is a dog-lover who’s had many dogs that’s she loved and cared for through out the years. She is also a person who is extremely easy to talk to and wil... (more)"

Confirmed Holiday Availability
11. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

56 repeat clients

"Lori stayed overnight at our house during the week we were overseas. She sent us pictures every day and worked with my mom and sister to manage the dogs (we ... (more)"

12. Emily

Will run or snuggle on couch :)

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"So great to have someone keeping my pup happy while we're gone! Great communication! (more)"

13. Andrew

I love dogs and they love me!

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Andrew has lived with and/or taken care of dogs his whole life. I actually get jealous that Andrew always has a better connection with the dog then me - rega... (more)"

Confirmed Holiday Availability
14. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

59 repeat clients

"We were so happy to find Amber to watch our dog over the weekend. Zeke is recovering from surgery so had some special needs and he was so well taken care of!... (more)"

15. Jake

Love to play with all dogs!

Upper East Side, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Jake has diligently helped care for his family's dog, Ziggy, ever since they got her as a puppy. He takes her on long walks, plays with her, feeds her and ha... (more)"

Confirmed Christmas Availability
16. Taylor

Full-time Pupper Lover

Juneau Town, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Baxter loves when Taylor stays with him. Having Taylor care for my Baxter boy puts my mind at ease while I'm away from home. Taylor is reliable, responsible,... (more)"

17. Nicole

Love dogs and dogs love me

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Nicole is one of the most loving, caring people I know. She has cared for my cat since she was a kitten and has always done a wonderful job. Her true passion... (more)"

18. Jo Ann

I want to connect with your pet!

Riverwest, Milwaukee, WI, 53212

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

6 repeat clients

"Our dogs absolutely love Jo! They had a great time with her and when we had a medical delay, she went above and beyond to make sure the boys were taken care ... (more)"

Confirmed New Years Availability
19. Ala

Like 2 wlk alone, luv 2 wlk w/ dogs

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Ala has been a great pet sitter for my two dogs over the past few years. Not only is she great with the dogs, she is also very reliable, leaves our house sp... (more)"

20. Dylan

Doggo-Lover in need of Doggos

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Dylan did an awesome job with Lana. She had recently had ACL surgery and was a bit of a handful in terms of care, but Dylan was very attentive to her needs a... (more)"

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: