Dog Boarding in Hillside, Milwaukee

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

Confirmed Easter Weekend Availability
1. Daniela & Michael

Paws Down, the Best in Town!

Lower East Side, Milwaukee, WI, 53202

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

80 repeat clients

"Thanks Daniela and Michael for taking such good care of Kinley! Communication with Daniela was awesome! From the drop off, to the daily pictures and updates ... (more)"

2. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

12 repeat clients

"Brian and Becky were incredible. We really appreciated the thorough meet and greet we had with them prior to our dogs stay. They made sure to really get to k... (more)"

3. Camry

Caring College Students

Avenues West, MILWAUKEE, WI, 53233

Dog Boarding

3 repeat clients

"Highly recommend Camry! She was flexible with drop-off and pick-up times (even when the pick-up was delayed by hours while I was traveling), sent adorable p... (more)"

Confirmed Easter Weekend Availability
4. Tia

Dog Goddess

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding

97 repeat clients

"We did an initial meet and greet to make sure everything was good. Tia was all set up and ready for us. She made sure everyone was comfortable and was even a... (more)"

5. Jennifer

Love and Play while You're Away

Bay View, Milwaukee, WI, 53207

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

"Wonderful experience!!! I felt completely comfortable leaving Penny with Jennifer who is very knowledgeable about dogs. I really appreciated getting pictures... (more)"

6. Vanessa

Great Home in BayView w/Fenced Yard

Bay View, Milwaukee, WI, 53207

Dog Boarding, Dog Walking

9 repeat clients

"As always, Vanessa was fantastic: professional, friendly, and great with communication. Scout had a great time staying with her and playing with Luna. We can... (more)"

7. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

9 repeat clients

"Sandy was a lifesaver! She took great care of our pups. They loved their stay and actually seemed bummed to leave when we got them in the car. I highly recom... (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

"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. Macaulay

We are lifetime dog lovers.

Walker's Point, Milwaukee, WI, 53204

Dog Boarding

"My dog was very well taken care of. He is actually missing his play buddy Belle. Two hands our better than one! Thanks MacCauley! (more)"

10. Rebecca

Can I pet your dog?

Juneau Town, Milwaukee, WI, 53202

Dog Boarding

4 repeat clients

"Becky did great with Finley. I don't even think Finley missed us while we were away for the weekend, and when we picked her up on Sunday afternoon she slept ... (more)"

11. Sarah

The Great Kind Of Dog House.

West Milwaukee, WI, 53215

Dog Boarding

6 repeat clients

"Sarah and family were very sweet to Maddie. They took her on nice walks and welcomed her with open arms into their pet friendly home. All of our dog's needs... (more)"

12. Staci

Calling all East Side Pets!

Lower East Side, Milwaukee, WI, 53202

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

6 repeat clients

"NeilYoung was happy and relaxed when I picked her up and then back at home. Staci made me feel very at ease about my little princess staying with her. (more)"

13. Nick

I'm happy too watch your dog!

Bay View, milwaukee, WI, 53207

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

20 repeat clients

"He did a good job of taking care of our dog at the last minute when we had to go out of town for the day. Nick made the time and took extremely good care of ... (more)"

14. Robert

Let's take a walk in the park!!

Bay View, Milwaukee , WI, 53207

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

1 repeat client

"Finn came home happy and tired and content, signs of being well cared for. Thank you, Robert, for taking on such a high energy dog with not much background h... (more)"

15. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

"Carolina is someone who is patient and considerate when listening to our needs for our sweet senior dog. We know our baby is safe and happy when she's there,... (more)"

16. Tori

Gifted animal trainer and lover

Upper East Side, Milwaukee, WI, 53211

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

About: When I was 7 I got my first dog, a yellow Labrador who passed a few years ago. Since then I have recently adopted two dogs. One as a year old, the... (more)

17. Heather

Work From Home Dog Lover

Story Hill, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

12 repeat clients

"This was ziggy's first stay away from home with other than family or friends. What can I say, Heather was wonderful! She sent me picture updates, Ziggy see... (more)"

18. Cullen

U.S. Marine and MKE educator

Murray Hill, Milwaukee, WI, 53211

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

"Cullen is kind and responsive, and was readily available when we needed him. Dropoff and pickup both went well, and Fenway seemed very happy to have spent th... (more)"

19. Trevor

Active dog loving couple downtown

Brewer's Hill, Milwaukee, WI, 53212

Dog Boarding, Doggy Day Care

2 repeat clients

"Trevor did a great job watching my two dogs. His home was A great set up for dogs in general Because it has a big fenced in backyard. I felt sure that my dog... (more)"

20. Michael

East side, close to beach and parks

Murray Hill, Milwaukee, WI, 53211

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

About: I have always grown up with animals in the home, from cats to bunnies and always plenty of dogs! After venturing to the midwest for grad school, my... (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: