Dog Boarding in Hillside, Milwaukee

Find a loving dog sitter to watch your dog overnight at your sitter's home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Samantha

Home full time & love to walk!

Northpoint, Milwaukee, WI, 53211

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

"I can't say enough good things about Sam! She has been dog sitting for my puppy for the past 3 weeks. She is caring, responsible, and fun. Oliver (my pup) li... (more)"

Confirmed availability
Christmas and New Year
2. Tia

❤️Professional Dog Lover❤️

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding

"This was Trouble's first stay away from home, and only his second stay away from us at all. Tia made us feel very comfortable leaving him in her care, and th... (more)"

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3. Kayla

Young dog-lover!

Bay View, Milwaukee, WI, 53207

Dog Boarding, House Sitting

"We were very happy with the care our little Tinkerbell got while staying with Kayla. Kayla was professional, caring and flexible with our schedules. She pr... (more)"

4. Deann

Multiple walks and cuddles!

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

"Deann was a great sitter! She sent picture updates and Tucker got to go on walks. He was a happy dog when I picked him up. I'll definitely ask Deann to watch... (more)"

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5. Lori

Home full-time - available to host

Upper East Side, Milwaukee, WI, 53211

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

"Lori and her husband were fantastic! Lori sent a number of updates and photos. Our pup came home well exercised and happy. Would highly recommend Lori to any... (more)"

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6. Tori

Home full time! Dogs are my love!!

Enderis Park, Milwaukee, WI, 53210

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

"Tori was amazing! My two pups peaches and phin had a great time on their over night stay. Tori is was in constant contact with me before and during their sta... (more)"

Confirmed availability
Christmas and New Year
7. Maria

Duplex with a fenced yard.

Burnham Park, Milwaukee, WI, 53215

Dog Boarding, Drop-In Visits, Dog Walking

"As a long time friend of Maria, I can confidently vouch for her empathy and compassion towards dogs, cats, and every animal in between. A kind soul, Maria c... (more)"

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8. Christy & Lucas

Flexible availability!

Riverside Park, Milwaukee, WI, 53202

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

"Christy and Lucas took great care of our dog - Chouquette even came back a little depressed because she missed their dog Jojo :). Christy sent us picture eve... (more)"

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9. Hannah

Home full-time, love long walks!

Downer Woods, Milwaukee, WI, 53211

Dog Boarding

"Hannah was great with my little Maya. She sent photos of her having a good time and Maya seemed upset to leave! I’ll certainly bring her back. (more)"

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10. Alexis

Dog, hikes and walks lover

Upper East Side, Milwaukee, WI, 53211

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

"Alexis was wonderful! It was my first time using Rover and she exceeded all expectations. She kept us up to date with how our dog was doing, and sent lots of... (more)"

Confirmed availability
Christmas and New Year
11. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

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

"Amber and Barb are wonderful! They take such good care of my little Roxy, she even gets to sleep in bed with Amber. They have a wonderful play yard for the d... (more)"

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12. Meghan

Dog Loving Young Professional

Lower East Side, Milwaukee, WI, 53202

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

"My Olive absolutely loves staying over with Meghan. She's been so good with her and Olive always greets her with so much excitement. She has also been extre... (more)"

13. Gabriella

I’ll treat your dog like my family

Avenues West, Milwaukee, WI, 53233

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

"Gabriella did a great job taking care of Max. She sent numerous updates and made sure he got all the attention he needed. Would definitely recommend Gabriell... (more)"

Confirmed availability
Christmas and New Year
14. Framaris

Home full time-

Washington Park, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

"Hi! My name is Deisy Guio and I know Framaris Hernandez 11 years ago. She is a very careful and responsible person. I trust her 100% and that's the reason wh... (more)"

Confirmed availability
Christmas and New Year
15. Christine

Bjj coach and dog lover!

Historic Third Ward, Milwaukee, WI, 53202

Dog Boarding, House Sitting, Dog Walking

"Christine took good care of Chester. He really seemed to enjoy staying there. Christine always responded to my questions and was flexible on when I could pi... (more)"

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16. Addie

Active & will luv ur pup as my own!

Yankee Hill, Milwaukee, WI, 53202

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

"Addie was great with my aussie Maya. She was super flexible about my pickup time and lots of photos and updates. Maya was happy. I’ll certainly be back! (more)"

17. Matthew J

Large fenced in yard- Home fulltime

Riverwest, Milwaukee, WI, 53212

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

"Rue had so much fun staying with Matthew! We automatically trusted him in caring for our pup due to his knowledge about dogs and their behaviors. He constant... (more)"

Confirmed availability
Christmas and New Year
18. Sierra

Your Dog’s Best Friend :)

Upper East Side, Milwaukee, WI, 53089

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

"Sierra is awesome! Very quick to reply and super flexible on pick up and drop off times. My dogs stayed with her for nearly 3 weeks and they had a fantastic... (more)"

19. Stephen

Dogs are the best

Kilbourn Town, MILWAUKEE, WI, 53203

Dog Boarding, House Sitting

"Our dog Barley had a great stay with Stephen! He sent us lots of photos and updates showing how much fun they were having together while we were gone. Highly... (more)"

20. Natalie

I love your Dog already!

Lower East Side, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

"Natalie is AWESOME! My pup spent the weekend with her while I was away and I was so impressed by her care for Miley. She treated my dog as part of her own fa... (more)"

Pet parents turn to sitters on Rover.com when they're looking for overnight boarding for their dog. 1,089 owners have reviewed sitters in Hillside, Milwaukee, WI, giving them an average rating of 5.0/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect dog sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average dog boarding rates to get an idea before you start a conversation with a dog sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

Rover.com offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Hillside dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Hillside, Milwaukee, WI, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

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: