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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Available this weekend
1. Daniela & Michael

Paws Down, the Best in Town!

Lower East Side, Milwaukee, WI, 53202

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

62 repeat clients

"Daniela was amazing! When I returned my dog was happy, relaxed, and well exercised! I treat my dog like my child, and I would definitely leave her here aga... (more)"

Available this weekend
2. Tia

Dog Goddess

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding, Drop-In Visits

86 repeat clients

"Our dog Smokey can definitely be a handful as well as an escape artist, but Tia did such a great job taking care of him. She sent pictures and I never once w... (more)"

3. Camry

Caring College Students

Avenues West, MILWAUKEE, WI, 53233

Dog Boarding

2 repeat clients

"Went to Milwaukee for a couple days with my fiance for his birthday. Didn't want to leave our dog, Spike, at home so I turned to Rover. Came across Camry and... (more)"

4. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

8 repeat clients

"I have taken my three dogs to Sandy several times. I have a Golden named Molly and two Shih Tuz named Georgie and Gacie. Sandy gives them the run of the hous... (more)"

5. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

10 repeat clients

"Scout had an amazing stay! We received the cutest pictures and I could tell he was happy and comfortable away from home. Will definitely book again. (more)"

6. 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)"

Confirmed New Years Availability
7. Stephanie

Friendly, Experienced Dog Foster!

Milwaukee, WI, 53211

Dog Boarding, Dog Walking

1 repeat client

"Great experience! Our Goldendoodle, Finn, seemed very happy and comfortable here. Stephanie sent pictures and videos throughout our trip. It was great to see... (more)"

8. 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)"

Confirmed Holiday Availability
9. Heather

Work From Home Dog Lover

Story Hill, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

10 repeat clients

"Heather was fantastic! We can't say enough good. She took great care of Molly and sent us pics every day so we knew how well Molly was doing. (more)"

10. Sarah

The Great Kind Of Dog House.

West Milwaukee, WI, 53215

Dog Boarding, Doggy Day Care

2 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)"

11. 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)"

Confirmed New Years Availability
12. 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

15 repeat clients

"Awesome. Nick was great, so easy to coordinate and he was super accommodating wth my flight schedule. We did a meet and greet first, his dog Bambi is so swee... (more)"

13. Staci

Calling all East Side Pets!

Lower East Side, Milwaukee, WI, 53202

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

5 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)"

Confirmed Holiday Availability
14. Katherine

Reliable, devoted, diciplined.

Bay View, Milwaukee, WI, 53207

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

"Katherine has been a friend to many large dogs over the years, both her own and her friend's dogs; pitbulls, dobermans, great danes, afgan wolfhounds, etc. S... (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)"

Available this weekend
16. Cullen

U.S. Marine and MKE educator

Murray Hill, Milwaukee, WI, 53211

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

"Cullen is a very honest, kind and responsible individual. Cullen is very good a staying in contact and very accessible when needed. He is an athletic perso... (more)"

17. Rebecca

Can I pet your dog?

Juneau Town, Milwaukee, WI, 53202

Dog Boarding

1 repeat client

"Our sweet pea felt perfectly at home. Rebecca was very acomodating and such a (more)"

18. 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)"

19. Jaime

Leo and I love to meet new friends!

Lower East Side, Milwaukee , WI, 53202

Dog Boarding, House Sitting

2 repeat clients

About: I grew up with dogs and have a dog of my own right now. I couldn't imagine life without one! I am a teacher during the school year and during the s... (more)

20. Scott

Not your Grandpa's Dog sitter

Lower East Side, Milwaukee, WI, 53202

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

"Flexible. Good job with my dog (more)"

Experience exceptional service and a personalized match

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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: