House Sitting in Hillside, Milwaukee

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

1. Rachel

Fun and energetic college student

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"I have known Rachel since she was young and she has always been kind and considerate. I also know that she is crazy about dogs. When she first met our curren... (more)"

2. Nikki

Pro Dog Exerciser and Lover! :)

Northpoint, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, House Sitting, Dog Walking

4 repeat clients

"Lucy and Bella loved Nikki! She is super sweet, organized and punctual. The house was kept clean and she even brought our mail in. I highly recommend Nikki! (more)"

3. Lizzi

Dog's Best Friend

Downer Woods, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Lizzi took great care of my high maintenance cairn terrier. In fact, I think Winnie was really hoping for Lizzi (not me) when I returned home. Oh well, she... (more)"

4. Lydia

Dog (and Cat) Lover in the City

Murray Hill, Milwaukee, WI, 53211

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: A little about me - I grew up with a wonderful corgi (Bruce) and have carried that love of dogs with me out here to the city! I'm finishing my unde... (more)

5. Brady

I love animals as they love me.

Avenues West, Milwaukee, WI, 53233

House Sitting

"Memphis had a wonderful time with Brady. Brady communicated with us and sent several updates with pictures. He watched our house as well as the pup. It was s... (more)"

6. Danielle

Upbeat, openminded, respect for all

Northpoint, Milwaukee , WI, 53202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Danielle was wonderful! She took such good care of our dog and home while we were gone. We will definitely use her in the future! It is nice to have peace of... (more)"

7. Brenna

Dog Walker / Babysitter

Saint Joseph, Milwaukee, WI, 53210

House Sitting, Drop-In Visits

4 repeat clients

"Brenna was fabulous! She was super flexible with our continuously changing plans. My dogs and cat absolutely adore her and I felt so comfortable leaving them... (more)"

8. Daniela & Michael

Paws Down, the Best in Town!

Lower East Side, Milwaukee, WI, 53202

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

67 repeat clients

"We love these two! We know they love our dogs and they treat them like their own. (Sometimes we wonder if our dogs even want to come back home!!) It's so ... (more)"

9. Marianna

Reliable, active, loving sitter

Lower East Side, Milwaukee, WI, 53202

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

6 repeat clients

"I have only ever trusted my dog with 2 other people in the entire 6 years I owned him but after meeting Marianna, she quickly became the 3rd. She was great... (more)"

10. Lauren

Your dog won't be "ruffing" it

Bay View, Milwaukee, WI, 53207

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

8 repeat clients

"I was a bit nervous about leaving my dog and 2 cats for a long weekend, but I had no reason to be because Lauren took great care of them! When I returned ho... (more)"

11. Jo A

I want to connect with your pet!

Riverwest, Milwaukee , WI, 53212

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Joann is the most awesome Dog sitter! We have an aussie doodle and a golden retriever that call her Aunt Jo. She is flexible, helpful and available when we... (more)"

12. Chelsie

Your dog's comfort is my concern :)

Riverwest, Milwaukee, WI, 53212

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

3 repeat clients

"Chelsie was a fantastic dog sitter for my family! She communicated consistently during our time away, and that gave us peace of mind. Chelsie was thoughtfu... (more)"

13. Steven

Top notch, experienced dog care

Lower East Side, Milwaukee , WI, 53202

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Steven was great with my dogs. My older dog Murphy is elderly and infirm and Steven was patient and kind with her. I'd definitely trust my dogs with Steven... (more)"

14. Margaret

Experienced trainer and owner!

Murray Hill, Milwaukee, WI, 53211

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Margaret was terrific with our dog, Louis! He can be difficult, but she was patient and gentle. I can tell that they bonded. On top of that Margaret was a gr... (more)"

15. Katie

Student and wannabe dog owner

Avenues West, Milwaukee , WI, 53233

Drop-In Visits, House Sitting, Dog Walking

2 repeat clients

"Katie was an excellent dog/house sitter for us! She took the dog to the park and our house was immaculate upon return. We will definitely be using Katie agai... (more)"

16. Allison

Dog lover who can't afford her own

Cambridge Heights, Milwaukee , WI, 53211

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

"Allison was the only sitter I trusted with my beloved 10-year-old, slightly neurotic, sometimes naughty and always emotionally needy Jack Russell Terrier. M... (more)"

17. Margaret

Barking Mad to Dog Sit for You

Northpoint, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Maggie was wonderful!!!! It was my first time using Rover and leaving Henri (8 yr old yorkie) with someone besides a family member or close friend so I was ... (more)"

18. Liz

Huge Dog Lover for all doggy-care!

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Liz did an amazing job taking care of our pup. She even sent me updates throughout her stay. (more)"

19. Jaronsa

Loving, Caring and Patient Person

Lower East Side, milwaukee, WI, 53202

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

2 repeat clients

"Jaronsa was fantastic! Our dog loved her from the moment she walked in the door. We felt immediately comfortable with her taking care of our animals and hom... (more)"

20. Lexy

Aspiring dog trainer/local artist

Riverwest, Milwaukee, WI, 53212

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

1 repeat client

"I left my 17 year-old cat with Lexy for 16 days, and Lexy took great care of her! The moment that I dropped my cat off, I could tell that Lexy had a true pas... (more)"

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Learn About Premier

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: