House Sitting in Hillside, Milwaukee

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

1. Alex

Active and passionate about dogs!

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Alex has the biggest heart and will shower your dog with love and attention! She is extremely professional and will provide any updates you need. Alex is ver... (more)"

2. Lori

Experienced dog & cat sitter

Story Hill, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

34 repeat clients

"Lori took excellent care of Hope and our home during an in home stay over the holidays. We enjoyed getting updates and photos from Lori daily! It was aweso... (more)"

3. Colleen

Walks, Runs, and Belly Rubs.

Kilbourn Town, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Like many other people my pets are my family and I was very concerned about having somone care for them and love them when i went on a vacation. Colleen did ... (more)"

4. Daniela & Michael

Paws Down, the Best in Town!

Lower East Side, Milwaukee, WI, 53202

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

85 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)"

Available this weekend
5. Mabeth

Home full-time ❤️my 2rescued dogs

Bay View, Milwaukee , WI, 53207

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

"Mabeth takes care of my dog on a daily basis. She is caring and patient especially given that my dog is elderly, blind and often ill. She is a genuine anim... (more)"

6. Jo A

I want to connect with your pet!

Riverwest, Milwaukee , WI, 53212

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"JoAnn is a great dog sitter! She stayed overnight with my senior dog, texted lots up updates and photos, and didn't hesitate in asking any questions. She's... (more)"

7. Kristen

Milwaukee Dog Sitter

Muskego Way, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kristen did a great job taking care of our dogs and our house while we were out of town. She communicated well with us to let us know how things were going ... (more)"

8. Marianna

Reliable, active, loving sitter

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, 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)"

9. Jaronsa

Loving, Caring and Patient Person

Lower East Side, milwaukee, WI, 53202

House Sitting, Drop-In Visits

2 repeat clients

"Jaronsa was great!! She was very responsive and the girls loved her. I came home to happy dogs. I would definitely hire her again and would also recommend he... (more)"

10. Alison

Fun & Adventurous Dental Student

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Alison is so sweet with my pit/lab mix. She is kind and caring when walking him. I love that she is very accountable and always dependable. She hasn't missed... (more)"

11. 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)"

12. 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)"

13. Cassie

Full time animal lover!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: I love all animals and would be honored to meet yours! I love staying active with walking my own dog and would love the opportunity to walk and tak... (more)

14. Sonja

Passionate about life with animals!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Vacations should be relaxing, but when you have to leave your pet in someone else's care, a vacation can become very stressful. Over the last 3 years, we hav... (more)"

15. Brenna

Dog Walker / Babysitter

Saint Joseph, Milwaukee, WI, 53210

House Sitting, Drop-In Visits

4 repeat clients

"My dogs were calm and happy as ever when I got home from my long weekend away. I can tell they do very well when Brenna stays with them! she's great and tru... (more)"

16. Jenny

Has loved dogs since childhood!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"The entire time I have known Jenny, she has adored dogs. To give some context, Jenny and I have been best friends for 20+ years. Some of my earliest memories... (more)"

17. Melanie

Dogs and I are love at first sight

Riverside Park, Milwaukee, WI, 53211

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

1 repeat client

"Melanie is great with dogs! My staffordshire terrior Knox absolutely loves her, to the point he anticipates her arrival by waiting next to the door on days s... (more)"

18. Margaret

Experienced trainer and owner!

Murray Hill, Milwaukee, WI, 53211

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

3 repeat clients

"This was the first time having someone come into our house to take care of our dog and Margaret couldn't have been better! She was very accommodating before... (more)"

19. Margaret

Barking Mad to Dog Sit for You

Northpoint, Milwaukee, WI, 53211

Dog Boarding, 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)"

20. Cullen

U.S. Marine and MKE educator

Murray Hill, Milwaukee, WI, 53211

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

1 repeat client

About: As someone who has been a lifelong lover of animals and worked at a vet hospital during high school I am very familiar with understanding the needs... (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: