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. Sara

Experienced Sitter, Fenced Yard

Morgandale, Milwaukee, WI, 53215

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

"This was the second or third stay we booked with Sara and her daughter. The pups had a great time and we got tons of Proof of Life photos :) -- great communi... (more)"

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2. Tia

❤️Professional Dog Lover❤️

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding

"Tia was absolutely wonderful. I had a lot of anxiety leaving Brunswick with someone new. After our meet and greet, I felt completely at ease. She answered al... (more)"

3. Megan

I love your dog already!

Lower East Side, Milwaukee, WI, 53202

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

"Adele was the best sitter we have found on rover to days. She was very flexible with meeting us before the trip, asked us questions, and sent lots of pics du... (more)"

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4. Samantha

Home full time & love to walk!

Northpoint, Milwaukee, WI, 53211

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

"I can't say enough good things about Sam! She has been dog sitting for my puppy for the past 3 weeks. She is caring, responsible, and fun. Oliver (my pup) li... (more)"

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5. Janel

Dog cuddles = the best! Let's play!

Jackson Park, Milwaukee, WI, 53219

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

"Naru stayed with Janel during labor day weekend. She had an absolute blast there! Janel has two amazing dogs of her own that played really well with our dog.... (more)"

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6. Jo Ann

Home full time-fenced in yard

Riverwest, Milwaukee, WI, 53212

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

"Jo Ann was awesome! We were gone for a full week and Shandy totally bonded with JoAnn. We will request her whenever she is available for Shandy !!! (more)"

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7. Hannah

Great backyard for outside time!

Bay View, Milwaukee, WI, 53207

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

"Emma had so much fun at Hannah’s House! She didn’t want to come home!!! They played And went for walks. I got Pictures and videos so I knew she ways having a... (more)"

Confirmed availability
This weekend
8. Deann

Multiple walks and cuddles!

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

"Rory had a great time over at Deann’s! I will be bringing him back next time I go out of town! Thank you for keeping me updated with pics and not being too t... (more)"

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9. Andrea

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

"Lola was so well cared for and given much love and attention! The frequent updates and photos were wonderful. Lola and I are so grateful that we have found... (more)"

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10. Hannah

Home full-time, love long walks!

Downer Woods, Milwaukee, WI, 53211

Dog Boarding

"I've personally known Hannah for her entire life and she is an incredibly hard working and dedicated person to any task put before her. She has had much per... (more)"

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11. Alexis

Dog, hikes and walks lover

Upper East Side, Milwaukee, WI, 53211

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

"Alexis was wonderful! It was my first time using Rover and she exceeded all expectations. She kept us up to date with how our dog was doing, and sent lots of... (more)"

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12. Gabriella

I’ll treat your dog like my family

Avenues West, Milwaukee, WI, 53233

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

"Gabriella did a great job taking care of Max. She sent numerous updates and made sure he got all the attention he needed. Would definitely recommend Gabriell... (more)"

13. Matthew J

Large fenced in yard- Home fulltime

Riverwest, Milwaukee, WI, 53212

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

"My dog had a great time with Matt and his dogs. He got to spend a lot of time out in Matt's yard and I loved the pictures he sent. Matt was also great with t... (more)"

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14. Natalie

I love your Dog already!

Lower East Side, Milwaukee, WI, 53202

Dog Boarding, Drop-In Visits, Dog Walking

"Natalie is AWESOME! My pup spent the weekend with her while I was away and I was so impressed by her care for Miley. She treated my dog as part of her own fa... (more)"

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15. Lea

See Spot Stay by UWM

Downer Woods, Milwaukee, WI, 53211

Dog Boarding, Doggy Day Care

"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)"

16. Carrie Ann

Moore's Dog Sitting

Shorewood, WI, 53211

Dog Boarding, Doggy Day Care

"Bulleit came back as pooped as I've ever seen him from Carrie Ann's house. She was willing to take him in for the weekend on short notice when my original si... (more)"

Confirmed availability
This weekend
17. Amber

Doggie Paws N' Play

Walker's Point, Milwaukee, WI, 53204

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

"Amber & Barb took great care of my pup, Wink, while I was on vacation for a week! I got daily updates and photos of him and his new dog friends. When I came ... (more)"

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18. Michelle

I love dogs & like to be active!

Murray Hill, Milwaukee, WI, 53211

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

"Michelle would be an awesome dog sitter, walker, or owner. She is a amazing with animals, and is the first person I call when we need to be gone for an exten... (more)"

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19. Monica

Monica's downtown dog boarding

Lower East Side, Milwaukee, WI, 53202

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

"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)"

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20. Abigail

Saving the world by snuggling dogs

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Dog Walking

"I could not of booked a better sitter for Coco. I had to go to New York for a few days and this was my first time being away from her. Not only did Abigail m... (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: