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. Steve

Your dogs home away from home

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding, Doggy Day Care

7 repeat clients

"Steve was awesome and super accommodating. I got pictures of Waski everyday, and I know that Waski loved playing with all the other dogs. We will be back! (more)"

2. Tia

Dog Goddess

Lincoln Creek, Milwaukee, WI, 53218

Dog Boarding

167 repeat clients

"Tia was wonderful from start to finish. Extremely quick response time and photo updates during the vacay. My boys can be a handful but she said they're wel... (more)"

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3. Matthew J

Large fenced in yard- Home fulltime

Riverwest, Milwaukee, WI, 53212

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

2 repeat clients

"We felt very comfortable leaving Ruby with Matthew. This is our first experience with Rover.com and it couldn't have been better. We brought Ruby over prior ... (more)"

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4. Alyssa

Doggie paradise near many parks!

Bay View, Milwaukee, WI, 53207

Dog Boarding, Doggy Day Care

3 repeat clients

"Alyssa and Hunter were awesome dog sitters for Rusty! When we first met them they took the time to get to know Rusty. Once we left for our trip we received p... (more)"

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5. Alli

Home full time- fenced in yard

Bay View, Milwaukee, WI, 53207

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

3 repeat clients
No Reviews Yet

About: I own two large friendly dogs of my own and would love to welcome your dog into my house too. I work from home so they will never be unattended, my... (more)

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6. Andrea

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

13 repeat clients

"Andrea and her family are awesome!!:). We feel so comfortable every time our pup goes there! Winston also loves coming and gets so excited...:) (more)"

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7. Deann

Multiple walks and cuddles!

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Doggy Day Care

About: I know that our pets are an important part of our family and that's why they should be treated as such! I am a lover of all animals and I have had ... (more)

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8. Amanda

Love Dogs all shapes and sizes!

Johnson's Woods, Milwaukee, WI, 53214

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

5 repeat clients

"This was my first Rover experience, and I was very pleased. Amanda took great care of my dog and kept me updated during her stay. My dog is deaf and can be a... (more)"

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9. Carrie Ann

Moore's Dog Sitting

Shorewood, WI, 53211

Dog Boarding, Doggy Day Care

33 repeat clients

"I was so happy to find Carrie Ann. It was a relaxing environment. Her fenced in backyard allowed for lots of playtime for my dog. I can tell when we picked h... (more)"

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10. Jo Ann

Home full time-fenced in yard

Riverwest, Milwaukee, WI, 53212

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

8 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)"

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11. Mackenzie

Interactive part-time caretaker

Kilbourn Town, Milwaukee, WI, 53203

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

1 repeat client
No Reviews Yet

About: Hello, I’m Mackenzie. I love dogs of all sizes and ages. I grew up with one Yorkshire Terrier and Two Yorkie-Poos, one of which was mine and I was ... (more)

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12. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting, Drop-In Visits

21 repeat clients

"Sandy was a lifesaver! She took great care of our pups. They loved their stay and actually seemed bummed to leave when we got them in the car. I highly recom... (more)"

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13. 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)"

14. Caroline

Home full-time

Historic Third Ward, Milwaukee, WI, 53202

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

"Caroline and Dan are both very knowledgeable and friendly! They were very accommodating with my hectic schedule and kept me updated during Ty's stay. Thanks! (more)"

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15. Tatiana & Tyler

Everything You Need Under One Woof.

Downer Woods, Milwaukee, WI, 53211

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

3 repeat clients

"Tatiana and Tyler were really great with my pup Obie! They made sure to keep me up to date on his stay and even sent me a cute picture. I would definitely r... (more)"

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16. Payton

A Doggo A Day Keeps The Doctor Away

Upper East Side, Milwaukee, WI, 53211

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

"Payton was amazing! She really helped me out in an emergency, on VERY short notice. She was able to accommodate my tricky drop off/pick up schedule. She was ... (more)"

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17. Kim

Looking for walking buddies!

Riverwest, Milwaukee, WI, 53212

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

"My Boston Terrier Mac loves Kim! She's very kind and caring, and I trust Kim to walk, play and keep him safe when I travel. Mac is always excited to see Kim ... (more)"

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18. Monica

Monica's downtown dog boarding

Lower East Side, Milwaukee, WI, 53202

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

16 repeat clients

"Our dog stayed with Monica for 8 nights and knew he was in great hands while we were out of town. We received numerous photos throughout the week. With her ... (more)"

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19. Abigail

Saving the world by snuggling dogs

Riverwest, Milwaukee, WI, 53212

Dog Boarding, Dog Walking

4 repeat clients

"Abby was a great sitter for our puppy! I appreciated the pictures and updates over the weekend, and was grateful for her personal attention to making sure ou... (more)"

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20. Taylor

Full-time Pupper Lover

Juneau Town, Milwaukee, WI, 53202

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

"Taylor was amazing! My dog is a timid/shy dog and Taylor made her feel comfortable. I will definitely be using her again! (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: