Dog Boarding in Hillside, Milwaukee

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

1. Tia

Dog Goddess

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding

93 repeat clients

"We all loved our experience with Tia! Kirby had such a great time. He's a shy puppy so we worried a little, but he came home to us a more rounded puppy - exh... (more)"

2. Daniela & Michael

Paws Down, the Best in Town!

Lower East Side, Milwaukee, WI, 53202

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

75 repeat clients

"Daniela was amazing as always! We needed a last-minute sitter when my wife went into labor, and Daniela was flexible and kind enough to change her plans for ... (more)"

3. Amy

A fun, caring & loving dog sitter!

Walker's Point, Milwaukee, WI, 53204

Dog Boarding

1 repeat client

"My 5 month old puppy stayed with amy and shilo for the weekend, she was very good with her and kept me updated and sent pictures all weekend. My puppy can be... (more)"

4. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

11 repeat clients

"Brian and Becky are outstanding caregivers! Communication throughout the booking process was extremely prompt, and we received lots of updates and pictures o... (more)"

5. Vanessa

Great Home in BayView w/Fenced Yard

Bay View, Milwaukee, WI, 53207

Dog Boarding, Dog Walking

9 repeat clients

"My family took a vacation over Thanksgiving. Because of the holiday all of the people that my wife will let watch her one and only daughter (Baby Maria) had... (more)"

6. Camry

Caring College Students

Avenues West, MILWAUKEE, WI, 53233

Dog Boarding

2 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)"

7. Sarah

The Great Kind Of Dog House.

West Milwaukee, WI, 53215

Dog Boarding

6 repeat clients

"We left our dog with Sarah and her family for a week while we were on vacation and it was a great choice. Sarah sent us many updates which made us feel bett... (more)"

8. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

9 repeat clients

"Sandy is wonderful to work with. She was flexible with our drop off and pick up times, and she even helped us by picking up our pup during our wedding ceremo... (more)"

9. Wanda

I love taking care of pets.

Whitefish Bay, WI, 53217

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

3 repeat clients

"Wanda was fantastic! She was kind and communicative. Our dog was happy and so am I. Thank you Wanda! (more)"

10. 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

2 repeat clients

"Dogs were well cared for, I think almost more spoiled than at our house and they were exhausted when we got home which was fantastic as so we're we. Also, R... (more)"

11. 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)"

12. Rebecca

Can I pet your dog?

Juneau Town, Milwaukee, WI, 53202

Dog Boarding

2 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)"

13. Staci

Calling all East Side Pets!

Lower East Side, Milwaukee, WI, 53202

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

6 repeat clients

"Staci was great with our little guy, Watson. From the meet and greet to drop off and pick up, we felt super comfortable with her friendliness and level of pr... (more)"

14. 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

17 repeat clients

"Nick was a great help with watching Zoey for the weekend! He was very accomodating with our schedule/plans and I could tell Zoey felt right at home with all... (more)"

15. Melainie

Your pups home away from home!

Lower East Side, Milwaukee, WI, 53202

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

"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)"

16. Trevor

Active dog loving couple downtown

Brewer's Hill, Milwaukee, WI, 53212

Dog Boarding, Doggy Day Care

2 repeat clients

"Travel and Kristen took great care of Zuma, and we're very conscientious to ask about his car instructions. He was all brushed and soft when we picked him u... (more)"

17. Stephanie

Energetic, caring dog lover!

Northpoint, Milwaukee, WI, 53202

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

"Stephanie is a fun and energetic friend that brings joy to everyone she meets. She is a very responsible person and has a lot of experience working with anim... (more)"

18. 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)"

19. Dante

Happiness is a warm puppy.

Walker's Point, Milwaukee, WI, 53204

Dog Boarding, Doggy Day Care, Dog Walking

"Dante was great we would happily have her watch our dog again. Thanks! (more)"

20. Kimberly

Walker's Point dog lover

Walker's Point, Milwaukee, WI, 53204

Dog Boarding, Drop-In Visits, Doggy Day Care

About: My name is Kimberly and I live in the Walker's Point area! I am a huge dog lover and always have since I was a child. My family always had them whi... (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: