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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. Siri Verified Background Check

Very flexible dog lover!

Lower East Side, Milwaukee, WI, 53202

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

"Siri is amazing with my pup! Macky can be a tempered little bull dog, but Siri gives him the love he needs! She is soo great!! Would HIGHLY recommend. (more)"

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2. Ryan Verified Background Check

Large fenced yard w/ toys:)

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Doggy Day Care

"Ryan is great. My dogs came back happy and tired. I’d almost say too good if that was a bad thing - my puppy didn’t even act like she missed me. I also boarded… (more)"

3. Andrea Verified Background CheckRover 101

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

"Lola was so well cared for and given much love and attention! The frequent updates and photos were wonderful. Lola and I are so grateful that we have found A… (more)"

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4. Katrina Verified Enhanced Background Check

Home Full Time- Always Available!

Town Of Lake, Milwaukee, WI, 53207

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

"Granger was so happy to see his buddies again! He’s currently passed out on the couch after another great vacation weekend at Katrina’s. See you in August! (more)"

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5. Cindy Verified Background Check

TOTAL DOG LOVER :)

Wauwatosa, WI, 53222

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

"Cindy went above and beyond. She was great at sending photos and keeping me in the loop. Followed all my instructions for feeding and made sure Maverick played… (more)"

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6. Kelly Verified Background Check

home full time with fenced yard!

Story Hill, Milwaukee, WI, 53208

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

"Kelly was great with our dog CC, and we will definitely be using her again in the future when we go out of town. She arranged for us to meet beforehand so CC c… (more)"

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7. Ellisha Verified Enhanced Background Check

Experienced, Loving & Compassionate

Walker's Point, Milwaukee, WI, 53204

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

"Jayla enjoyed her stay! She had enjoyed many walks and runs along the Oakleaf trail. I had received updates on Jayla along with photos of her!! I will definite… (more)"

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8. Karen & Toy Verified Background CheckRover 101

Ready to play and cuddle

Tippecanoe, Milwaukee, WI, 53207

Dog Boarding, Doggy Day Care

"Great experience! My pups were so well cared for and they came home tired and happy. I loved the daily photos and videos updates. They even gave my stinky boys… (more)"

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9. Denise Verified Background Check

Make your next trip worry-free!

Honey Creek Parkway, Milwaukee, WI, 53213

Dog Boarding, House Sitting

"Denise was absolutely fabulous with my goofbutt! She sent updates regularly with photos, and asked permission before trying new things with him. He needed some… (more)"

10. Eileen Verified Enhanced Background Check

I already love your dog!

Lower East Side, Milwaukee, WI, 53202

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

"Our corgi Clyde had a fantastic stay with Eileen! She was great in sharing pics and updates, and Clyde got plenty of exercise and stimulation during his stay… (more)"

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11. Anne Marie Verified Background Check

My friends call me "Dog-Obsessed"

Upper East Side, Milwaukee, WI, 53211

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

"Anne Marie is an exceptional dog sitter! She sent us updates regularly, gave our dog their required meds and was an all around a fantastic communicator. We ar… (more)"

12. Daisy Verified Background CheckRover 101

I Love all animals

Harambee, Milwaukee, WI, 53212

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

"I really must apologize for being so late in doing this review. I have been on the road and not had a chance. Daisy was terrific, she kept in contact with us t… (more)"

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13. Auria Verified Background Check

Home full time, LOVE dogs!!!

Glendale, WI, 53209

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

"Auria was great with my dog! We were gone for a week and she sent me photos every day. He was happy and I like that she had dogs that he got along with and cou… (more)"

14. Lauren & Derek Verified Background Check

Must Love Dogs

Lower East Side, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

"Lauren and Derek did a great job watching our cocker spaniel! They allowed us to come over to see their place and meet them before we made a decision. While we… (more)"

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15. Jill Verified Background Check

Caring Animal-Loving Vegan 💜

West Allis, WI, 53227

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

"Jill and her husband took such great care of our two pups when we were out of town. It was our first time boarding them and we were a little nervous, but it wa… (more)"

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16. Sadie Verified Background Check

I’ll run with your dog!

Upper East Side, Milwaukee, WI, 53211

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

"Sadie was super accommodating after our original flight got cancelled, and was able to keep our dog for an extra day! She sent photos whenever we asked (which … (more)"

17. Christy & Lucas Verified Background Check

Dog and cat lover!

Cambridge Heights, Milwaukee, WI, 53211

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

"Christy & Lucas were very accommodating and flexible to work with my schedule. And my pup had so much fun during her stay she ended up sleeping off the excitem… (more)"

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18. Megan Verified Enhanced Background Check

Mama Meg’s Doggy Daycare Services

West Allis, WI, 53219

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

"She was so wonderful! She provided pictures and updates throughout my dogs stay. Her home was clean and her backyard totally fenced, great for pups to play in … (more)"

19. Deann Verified Background Check

Multiple walks and cuddles!

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

"Deann and her family were amazing with our two dogs! She sent me pictures and updated me daily. We were able to have a stress free time away knowing our pups w… (more)"

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20. mkjjkelley@sbcglobal.net Verified Background Check

Friendly, Fun and Faithful Care

Wauwatosa, WI, 53213

Dog Boarding, Drop-In Visits, Dog Walking

"I am so happy to have found such a wonderful dog sitter! Karen (and Michael) are very quick to respond to messages and I received great updates while we were … (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: