Dog Boarding in Hillside, Milwaukee

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

1. Daniela & Michael

Paws Down, the Best in Town!

Lower East Side, Milwaukee, WI, 53202

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

67 repeat clients

"Leon, Fury and Margie seemed to have LOVED their visit with Daniela and Mike. I was so comfortable leaving them with at their home. We met before hand and Mi... (more)"

2. Tia

Dog Goddess

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding

91 repeat clients

"Tia was amazing. She has very extensive knowledge about dogs needs, behavior and training. She seemed to go out of her way to address our concerns and prov... (more)"

3. Amy

A fun, caring & loving dog sitter!

Walker's Point, Milwaukee, WI, 53204

Dog Boarding

1 repeat client

"Amy was so accommodating taking Benji last minute. She made him feel right at home and me at ease and sent me lots of pictures. She had lots of space, a back... (more)"

4. Camry

Caring College Students

Avenues West, MILWAUKEE, WI, 53233

Dog Boarding

2 repeat clients

"We felt at ease leaving Willie with the girls for a few days. Communication was timely and easy. They were very accommodating in scheduling drop off and pick... (more)"

5. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

10 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)"

6. Mattie

Easy-going, Reliable, Lover of dogs

Riverwest, Milwaukee, WI, 53212

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

1 repeat client

"Mattie was very easy to communicate and coordinate our 13 year old Whippet, Becca's 2-night stay in her home. Becca has settled in very easily since she came... (more)"

7. Sarah

The Great Kind Of Dog House.

West Milwaukee, WI, 53215

Dog Boarding, Doggy Day Care

3 repeat clients

"Sarah was great w our dog Marty! Kept us up to date all weekend with photos. Marty had a great time hanging out with his new girlfriend Lucy. We would defini... (more)"

8. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

8 repeat clients

"Sandy is amazing! She really went above and beyond, and this was the first time she took care of Jackson. He has separation anxiety and needed someone to... (more)"

9. 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

16 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)"

10. Trevor

Active dog loving couple downtown

Brewer's Hill, Milwaukee, WI, 53212

Dog Boarding, Doggy Day Care

2 repeat clients

"We want to thank you with all our heart for taking outstanding care of our dogs, Trevor was awesome! I am very thankful for Trevor, his professionalism, and ... (more)"

11. Stephanie

Friendly, Experienced Dog Foster!

Milwaukee, WI, 53211

Dog Boarding, Dog Walking

1 repeat client

"Stephanie did a great job taking care of Gordon while I was away for five nights. He can be shy with strangers but he warmed right up to her! She took him to... (more)"

12. Heather

Work From Home Dog Lover

Story Hill, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

11 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)"

13. Rebecca

Can I pet your dog?

Juneau Town, Milwaukee, WI, 53202

Dog Boarding

1 repeat client

"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)"

14. Staci

Calling all East Side Pets!

Lower East Side, Milwaukee, WI, 53202

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

5 repeat clients

"Staci's dog and my own got along very well. My dog was happy and TIRED after leaving. Staci was also flexible with my pick up time. If I travel to Milwauk... (more)"

15. Matt

Dogs get all my care and love

Lower East Side, Milwaukee, WI, 53202

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

"Matt was fantastic! Very polite and courteous. He responded anytime I text or called and he was great with my dogs. I received pictures from Matt everyday a... (more)"

16. 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)"

17. 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)"

18. Ethan

No dog too energetic or old for me!

Juneau Town, Milwaukee, WI, 53202

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

1 repeat client

"He did an awesome job with our high attention Bulldogs- and on short notice! His place is the perfect set up with a dog park close by. Our dogs aren't easy a... (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. Mathew

Look at this eye-catching headline

Juneau Town, Milwaukee , WI, 53202

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

"Great dog walker and dog sitter. Very reliable, respectful, and responsible. I would would use him again in a heart beat. I have 4 dogs 2 cats and a 2 mice a... (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: