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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1. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

4 repeat clients

"Lola and Watson lived thier stay! They were tired from playing with duke in the awesome big backyard. Will definitely recommend and stay again. (more)"

2. Daniel

warm comfortable caring environment

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

22 repeat clients

"Daniel and his family did a wonderful job caring for our dog. They accommodated our request for boarding with short notice. Daniel quickly responded to all... (more)"

3. Andrea

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

8 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)"

4. Daniela & Michael

Paws Down, the Best in Town!

Bay View, Milwaukee, WI, 53207

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

104 repeat clients

"Daniela & Michael took fabulous care of Sadie! She was alert, happy, and wanted to play more when we picked her up. They sent updates throughout her stay, an... (more)"

5. Monica

Monica's downtown dog boarding

Lower East Side, Milwaukee, WI, 53202

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

6 repeat clients

"Very flexible with schedule changes. Watched my pup Chloe over the Christmas holiday and sent a lot of pictures. Chloe seemed in top order when I picked her... (more)"

6. Tia

Dog Goddess

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding

148 repeat clients

"Tia was absolutly amazing! I had so much anxiety about leaving my babies she made me feel so comfortable. She sent me pictures and kept me updated. Because o... (more)"

7. Tori

Dogs are my passion!

Upper East Side, Milwaukee, WI, 53211

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

1 repeat client

"Tori did a great job with Ginger. She was very flexible with pick up and drop off times, which was very convenient. She sent pictures with an update of how m... (more)"

8. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Carolina was great! Ari felt right at home from the moment we walked in. She took several pictures throughout her stay and also went on nice long walks. Ari ... (more)"

9. Laura

Bleeding heart dog lover

Bluemound Heights, Wauwatosa, WI, 53213

Dog Boarding, Drop-In Visits, Doggy Day Care

2 repeat clients

"Badger had a nice stay with Laura! She was sweet to him and made him feel right at home with her dog. Hopefully he will be staying with her again soon. (more)"

10. Carrie Ann

Moore's Dog Sitting

Shorewood, WI, 53211

Dog Boarding, Doggy Day Care

29 repeat clients

"Excellent sitter! Very loving and friendly household. Our old girl got to sleep with Carrie Ann's teenaged son (!) and our younger boy dog had a blast runnin... (more)"

11. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

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

54 repeat clients

"My 3 month old puppy is a handful but she stayed with Amber and Barb for a week and had a blast! They sent daily videos and pictures which was really nice f... (more)"

12. Rebecca

Loves long walks on the Riverwalk!

Lower East Side, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

"I don't think I know anyone who loves dogs more than Rebecca. If your number one concern is having someone take care of your dog who treats them just as well... (more)"

13. 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)"

14. Lea

See Spot Stay by UWM

Upper East Side, Milwaukee, WI, 53211

Dog Boarding, Doggy Day Care

2 repeat clients

"This was my dogs' first visit with Lea. They adore her, and she took great care of them. I also found Lea flexible and very easy to communicate with. I would... (more)"

15. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

10 repeat clients

"Sandy was absolutely wonderful! You can tell she is a true animal lover. I felt so at ease when my little pup was there as she sent updated pictures througho... (more)"

16. Julie

Large fenced yard and a Lab buddy

Wauwatosa , WI, 53213

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

"Julie was great! Yoda got along with Chevy and Julie's kids were a big help! Would definitely recommend! (more)"

17. 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

24 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)"

18. Scott

Scots EastSide Doggy Daycare

Murray Hill, Downer Woods, WI, 53211

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

"Our dog Pax had a great stay with Scott and his dog Texas. Scott was easy to coordinate with and everything went great. And our dog Pax has a new best friend... (more)"

19. Katie

Born with a love for dogs

Juneau Town, Milwaukee, WI, 53202

Dog Boarding, Dog Walking

"Katie loves dogs and is very responsible. She's a high energy, positive woman and is great with dogs of all sizes, energy levels and temperaments. She has vo... (more)"

20. Rebecca

Can I pet your dog?

Juneau Town, Milwaukee, WI, 53202

Dog Boarding

4 repeat clients

"Becky did a wonderful job taking care of our dog Zuzu for two and a half weeks, which was the longest we had ever been separated. She sent us photos and upd... (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: