Pet Setting & Drop Ins in Hillside, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

Available this weekend
1. Lori

Experienced dog & cat sitter

Miller Valley, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

47 repeat clients

"I needed a pet sitter quickly. I just moved to the area and haven't had the time nor needed a sitter but something came up last minute and I was in need of o... (more)"

2. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"At first I was hesitant with using Rover.com. When I met Carolina she was very attentive to Blossom’s needs. After meeting Carolina, I was definitely comfort... (more)"

3. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

22 repeat clients

"I won't trust anyone but Brian and Becky with my baby Rock! Brian has a calming way with dogs and is a dream come true. My doggie and I both feel very lucky ... (more)"

4. Racheal

Never met a dog I didn't like

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

About: I've had dogs of all sorts and sizes my entire life. From training to going for walks to simply hanging on the couch, I always enjoy furry company... (more)

5. Katryn

Ready to Meet the Dogs of MKE

Historic Third Ward, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

"Katryn is a natural when it comes to dogs. She was with my 3 bulldogs for a whole weekend and was wonderful! They loved her so much they were always in the s... (more)"

6. Paige

Home full-time, will jog with dog!

Murray Hill, Milwaukee, WI, 53211

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

"Paige is absolutely wonderful with animals and has done an incredible job sitting for my family's dog in the past! 10/10 would recommend. She was kind, court... (more)"

7. Brooke

Caring & Experienced Dog Sitter

Riverside Park, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Brooke did a wonderful job! When we got home our dogs were happy and tired. While we were gone Brooke took pictures of our dogs and let us know what they did... (more)"

8. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Sarah is amazing! Our dog is 8 weeks old and she helped us a ton while my wife and I were at work. Thank you so much Sarah!! Best part of my morning was gett... (more)"

9. Hunter

Dog lover exploring Milwaukee!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"I've known Hunter since he was a young boy. We've always had dogs and Hunter has always been very good with them. He is gentle but firm. Our dogs were always... (more)"

10. Melainie

Your pups home away from home!

Lower East Side, Milwaukee, WI, 53202

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

1 repeat client

"Lainie was a real life saver with my German Shepherd, Wahoo, when I knew I was going to be stuck late at work. He's a friendly dog in general, but he had nev... (more)"

11. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Laurie was a consummate professional in our home and highly experienced and skilled with my dogs! I can't say enough nice things about Laurie, she instantly ... (more)"

12. Samantha

Sam's Dog Days

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"This was the first time leaving the little ones at the house by themselves and Sam was great! Our Morkie had already made fast friends on the meet and greet ... (more)"

Available this weekend
13. Jonathon W. & Kelsey

Great for last minute requests!

Harambee, Milwaukee, WI, 53212

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

4 repeat clients

"They are both great! They were so flexible and were able to handle my last minute request to watch him. I was able to go through my day knowing Diesel was in... (more)"

14. Jessica

Will Run/Hike for K9 Kisses!

Upper East Side, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"Jessica watched our dog Bosun this past Friday. Took fantastic care of him and sent us some great photos of their adventures. Will definitely book again. ... (more)"

15. Kayley

I go on a lot of walks with dogs

Downer Woods, Milwaukee, WI, 53211

Drop-In Visits, Dog Walking

About: I am 21 years old and I have been around dogs my whole life. When I lived with my parents I had one dog at my mom`s house and two dogs at my dad`s ... (more)

16. Helen

Caring Cat Sitter and Dog Walker

Yankee Hill, Milwaukee , WI, 53202

Drop-In Visits, Dog Walking

3 repeat clients

"This is my first time ever using Rover and Helen was great! She was communicative, took both my dogs on a great, long walk and sent me pictures of them! I'll... (more)"

17. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

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

57 repeat clients

"We had a pretty last minute request for a dog sitter, and we just stumbled on DogVacay. I got a little confused by the site, but Amber helped me through all... (more)"

18. Emily

Caring, Committed & Active

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Emily frequently dog sat our lovable lab, Boomer! Boomer loved his time with Emily. She was very responsible and spent quality time with him. We always kn... (more)"

19. Monica

Monica's downtown dog boarding

Lower East Side, Milwaukee, WI, 53202

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

8 repeat clients

"Monica took such great care of my dog max, he loves when she comes to take him for his walks. She has also kept him overnight while we were away on vacation.... (more)"

20. Madeline

Madeline's Dog Care

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I am a student at the Milwaukee School of Engineering in downtown Milwaukee. I lead a very active lifestyle so getting your pet the proper amount o... (more)

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Learn About Premier

When it comes to pet sitting, dog owners in Hillside, Milwaukee, WI love Rover.com. Over 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of pet sitting in Hillside may surprise you - in a good way. That's because there's a pet sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for pet sitting on Rover? Check out our average pet 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, Milwaukee drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 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, so you're sure to find the perfect pet sitter in Hillside, Milwaukee . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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: