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. Daniel

warm comfortable caring environment

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

38 repeat clients

"Daniel and his wife really set my mind at ease while watching my puppy. I received updates with pictures daily. With this being my pup's first overnight sta... (more)"

Confirmed Holiday Availability
2. Monica

Monica's downtown dog boarding

Lower East Side, Milwaukee, WI, 53202

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

10 repeat clients

"Monica was awesome and reassured me that she wanted both me and my dog to be comfortable during the stay. She regularly updated me with pictures and was very... (more)"

3. Andrea

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

10 repeat clients

"We were very happy with our experience with Andrea. Wrigley loved playing in the backyard and got along great with Molly. It was evident from the meet and gr... (more)"

4. Melainie

Your pups home away from home!

Lower East Side, Milwaukee, WI, 53202

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

1 repeat client

"Melainie did a great job watching Buddy. She sent lots of picture updates and was very patient with him. He is an older dog and can sometimes be very needy, ... (more)"

5. Jonathon W. & Kelsey

Great for last minute requests!

Harambee, Milwaukee, WI, 53212

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

9 repeat clients

"Crosby had a blast with Jonny and Kelsey over the weekend. They have a nice little side yard which was perfect for Crosby to run around in. Crosby came home ... (more)"

6. Rebecca

Loves long walks on the Riverwalk!

Lower East Side, Milwaukee, WI, 53202

Dog Boarding

"Rebecca was a wonderful sitter. She took care of my dog as I would have, he came home happy, and she reassured me that he was ok the whole time I was out of ... (more)"

Confirmed Holiday Availability
7. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

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

59 repeat clients

"Thank you Amber & Barb for taking such excellent care of Roxy! I loved seeing the pictures & videos of her. It is so nice the way you treat the dogs in your ... (more)"

8. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

19 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)"

9. Diane

24/7 - Delightful Doggy Daycare.

Riverwest, Milwaukee, WI, 53212

Dog Boarding

"Hi Diane, I would like to thank you for caring for our Black Labrador Retriever , the Week of August 21-28, 2017. Diane, you provided the best care that ... (more)"

10. Erendira

Outdoorsy dog loving student!

Bay View, Milwaukee, WI, 53207

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

1 repeat client

"Erendira was able to take Olaf on pretty short notice and was super accommodating of our schedule. She made sure our dogs would get along well and sent a cu... (more)"

Available this weekend
11. Abigail

Saving the world by snuggling dogs

Riverwest, Milwaukee, WI, 53212

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

"Abby is my go-to person for when I need a sitter for my special-needs senior fur baby! My dog cannot be left alone for long periods of time and requires medi... (more)"

Available this weekend
12. Carolina

Dog whisperer but not a dog lady

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"We highly recommend Carolina. She went above and beyond, taking care of our dog four days after our dog had to get unexpected surgery. She gave our pup her m... (more)"

13. Nicole

Trust-worthy, dog lover!!

Shorewood, WI, 53211

Dog Boarding

"Nicole is a very kind & trustworthy pet sitter who loves all animals. She is competent and knowledgeable about the care needed. When we travel we have peac... (more)"

14. Carrie Ann

Moore's Dog Sitting

Shorewood, WI, 53211

Dog Boarding, Doggy Day Care

31 repeat clients

"Carrie Ann and Kevin are super easy to work with and took excellent care of our pup! She updated us with pictures, daily statuses, etc. - so happy that we f... (more)"

15. Jo Ann

I want to connect with your pet!

Riverwest, Milwaukee, WI, 53212

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

6 repeat clients

"Thank you JoAnn for watching my dog for 3 nights in a row, walking him, and letting him be comfortable where ever he wanted in your home. Love your backyard ... (more)"

16. Quinn

Home 90%, will take swim&hike

Avenues West, Milwaukee, WI, 53233

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

2 repeat clients

"Willow had a great time with Quinn and Cleo.. so much so that she was visibly sad (and tired from playing!) when she came home. Quinn was very responsive to ... (more)"

17. Mckenzi

lots of walks/ playing

Lower East Side, Milwaukee, WI, 53202

Dog Boarding

"McKenzi has watched my two dogs numerous times She has her own dog, and us very caring and responsible She takes the dogs for walks morning and nights. An... (more)"

Confirmed Holiday Availability
18. Sarah

Responsible animal loving family

Lower East Side, Milwaukee, WI, 53202

Dog Boarding, Doggy Day Care, Dog Walking

"Sarah is kind, attentive, and loving toward Lola and welcomed her into her lovely family. Couldn’t ask for a better dog sitter! (more)"

19. Diana

reliable, flexible& loving sitter

Avenues West, Milwaukee, WI, 53233

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

"Good communication, easy to work with, dog was returned safe and happy. (more)"

20. Madeline

'Man's best friend's' best friend!

Kilbourn Town, Milwaukee, WI, 53203

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

2 repeat clients

"I recently adopted a 3 year old bulldog who had previously (more)"

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: