Dog Boarding in Hillside, Milwaukee

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

1. Daniel

warm comfortable caring environment

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

34 repeat clients

"My dog Hachi has stayed with Dan for 2 consecutive weekends. We get good updates and have peace of mind that my baby is safe with him. He had an injury the s... (more)"

2. Jonathon W. & Kelsey

Great for last minute requests!

Harambee, Milwaukee, WI, 53212

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

6 repeat clients

"Jonathon and Kelsey were awesome. One of my dogs gave them a very hard time, but they worked with it and went with the flow. They kept me updated and sent m... (more)"

3. 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 was awesome and reassured me that she wanted both me and my dog to be comfortable during the stay. She regularly updated me with pictures and was very... (more)"

4. Andrea

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

10 repeat clients

"The whole experience was wonderful. We planned a 10 day European vacation and were concerned about leaving our active Labrador retriever. Our dog had a gre... (more)"

5. Rebecca

Loves long walks on the Riverwalk!

Lower East Side, Milwaukee, WI, 53202

Dog Boarding

"Rebecca was a wonderful sitter. She took care of my dog as I would have, he came home happy, and she reassured me that he was ok the whole time I was out of ... (more)"

6. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

22 repeat clients

"Our Newfoundland boarded with Brian last week, and we are delighted to share the fact that this was a lovely experience! Brian and his wife are clearly warm... (more)"

7. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"Carolina was awesome. She took our puppy Archer on short notice! He had a great time and she even updated us with photos:) We would definitely use her agai. ! (more)"

8. 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

"Melanie was great with my new pup, Yuca. Yuca came back sleepy and happy, and Melanie kept in touch with me about how she was behaving and sent plenty of pic... (more)"

9. Kayla

Dog Mom

Wauwatosa, WI, 53072

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

"Riggins, our 4 month old Golden had a great stay with Kayla and her husband! We highly recommend using them for all of your pet needs! (more)"

10. Abbey

the reason u can escape 4 a weekend

Murray Hill, Milwaukee, WI, 53211

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

"Abbey is a good friend of mine who on multiple occasions has been willing to take care of my dog. Shes not the easiest dog to deal with due to frequent acci... (more)"

11. Madeline

'Man's best friend's' best friend!

Kilbourn Town, Milwaukee, WI, 53203

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

"Madeline was very nice and sensitive to our very old dog's needs and foibles. (more)"

12. Rebecca

Dog loving human ready to please!!

Brewer's Hill, Milwaukee, WI, 53212

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

"Becca was prompt, professional, and friendly. Once we met I knew immediately that Jack was in wonderful hands. She asked a lot of great questions about Jack'... (more)"

13. Katryn

Ready to Meet the Dogs of MKE

Historic Third Ward, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

"I have to agree with Devin! Katryn is a natural with dogs! My Boston tends to get overexcited very quickly when meeting new people and Katryn handled him lik... (more)"

14. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

15 repeat clients

"Dogs did soo well with Sandy! So thankful to find somewhere they can stay comfortably when we are gone. She was very accomodating and really appreciated she ... (more)"

15. Jo Ann

I want to connect with your pet!

Riverwest, Milwaukee, WI, 53212

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

5 repeat clients

"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)"

16. Alyssa

Work from home, Dog Lover

Historic Third Ward, Milwaukee, WI, 53202

Dog Boarding, Doggy Day Care

4 repeat clients

"Alyssa was great! She was accommodating with my busy schedule and sent me photos of my pup during the stay. Her dog Lilly was adorable and friendly and got a... (more)"

17. Quinn

Home full-time, will take swim&hike

Avenues West, Milwaukee, WI, 53233

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

2 repeat clients

"Quinn was amazing as our goldendoodle's first pet sitter. She sent adorable pictures that let us know that Mia was having a great time with her dog, Cleo. Qu... (more)"

18. 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

3 repeat clients

"Paige was absolutely amazing! I can't even begin to explain how wonderful she was. I can count the number of people I trust to care for my dog on one hand. ... (more)"

19. Mary

Attentive dog sitter, flexible hrs.

Riverside Park, Milwaukee, WI, 53211

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

About: I am a grad student at UWM with a flexible schedule. On days that I am available, I will be able to provide your dog with abundant attention to ens... (more)

20. Michelle

Excess Love for Sale

Historic Third Ward, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"Michelle was great. She was really accommodating. I had to leave town at weird hours, but wanted to spend as much time with my pup before I left and Michel... (more)"

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Learn About Premier

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: