Dog Boarding in Highwood Estates, 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. Melissa

Melissa's Comfort Zone

West allis, WI, 53227

Dog Boarding, Doggy Day Care, Dog Walking

25 repeat clients

"Melissa did an amazing job! Bailey had so much fun during her weekend away and I wasn't worried for a second. Melissa sent super cute pictures of Bailey duri... (more)"

2. Andrea

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

10 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)"

3. Daniel

warm comfortable caring environment

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

35 repeat clients

"My dog Hachi has stayed with Dan for 2 consecutive weekends. We get good updates and have peace of mind that my baby is safe with him. He had an injury the s... (more)"

4. Jill

I have two great dogs and a fence

Greenfield, WI, 53228

Dog Boarding

"I have known Jill for 6 years and can testify that she is exceptional with animals. In addition to having experience in pet training, the skills, love, and c... (more)"

5. Julie

Dogs complete the family!

Wauwatosa, WI, 53226

Dog Boarding, Doggy Day Care

10 repeat clients

"I would like to start by saying that when we picked our collie up he didn't want to leave. He has never stayed with anyone other than friends or family and u... (more)"

6. 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)"

Confirmed Holiday Availability
7. Sylvia

Very excited to care for your dog!

Fairview, Milwaukee, WI, 53219

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

1 repeat client

"Sylvia was great with our dogs! They instantly felt comfortable in her home and they were very happy when we picked them up! I would definitely recommend boo... (more)"

Confirmed Holiday Availability
8. Julie

Very flexible and inexpensive care

Clayton Crest, Milwaukee, WI, 53221

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

2 repeat clients

"My pup is a high energy guy, so I wanted to match him up with someone with a dog(s) that he could play with, and a person that I was comfortable with. Julie ... (more)"

9. Andrea

Cavalier mom who loves animals

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

5 repeat clients

"Andrea was incredible! Our dog is high energy and we were worried that we had to leave her for a week, but as soon as we met Andrea we knew we were in good h... (more)"

Confirmed New Years Availability
10. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

18 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)"

Confirmed Holiday Availability
11. Traci

Snuggles & Play While You’re Away

Jackson Park, Milwaukee, WI, 53219

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

"Traci was fantastic... She took great care of my girls. She sent lots of photos. It’s a huge relief knowing we have a better option then a kennel.. We Highly... (more)"

12. April

Doggone Awesome Pet Sitting

West Allis, WI, 53219

Dog Boarding

14 repeat clients

"Ronan and Pippen had a great stay at Aprils home. They were very well taken care of. I did not have to worry about them at all while I was gone. It was a gre... (more)"

Confirmed Holiday Availability
13. Esther

Your pet will feel like family

West Allis, WI, 53227

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

"Esther is an amazing person with a big heart and love for animals. She is reliable and will be an excellent dog sitter. You can count on Esther to give it he... (more)"

14. Maureen Casey

Love to get outside with your pup!

Wauwatosa, WI, 53213

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

2 repeat clients

"Maureen was great, and my crazy terrier was happy when I picked her up after 5 days. Lots of walks reported and prompt emails with status reports. Everythi... (more)"

15. Karen

Let's have fun!

Jackson Park, Milwaukee, WI, 53219

Dog Boarding, Doggy Day Care, Dog Walking

About: Our house is perfect for dog and puppy fun. My own dog, Roger, loves playing and snuggling with other dogs. He makes quick friends and is always up... (more)

Confirmed Holiday Availability
16. Angie

Loving Family to Care for your Dog

West Allis, WI, 53219

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

1 repeat client

"Angie and the kids did a great job taking care of my energetic pup for the weekend! They sent photo pupdates and maintained the perfect amount of communicati... (more)"

17. Zhanae

The best care for your best friend!

Greenfield, WI, 53221

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

4 repeat clients

"Having my furry one stay with Zhanae was a great experience. She was communicative, flexible with drop off and pick up times, and most importantly, took grea... (more)"

18. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

8 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)"

19. Ryan

I'll run, rough house, & romp!

River Bend, Milwaukee, WI, 53219

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

About: I've always had dogs, and I always enjoy playing with dogs. I'll play tug, fetch, chase, wrestle, you name it. Dogs can let out their wild side wit... (more)

Confirmed Christmas Availability
20. Amber

Welcome to our home!

Wedgewood, Milwaukee, WI, 53220

Dog Boarding

About: I have a very friendly chihuahua named Brutus who gets along with most pets! I’ve been caring for dogs for about 10 years and enjoy spending time w... (more)

When it comes to dog boarding, dog owners in Highwood Estates, Milwaukee, WI love Rover.com. Over 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of dog boarding in Highwood Estates may surprise you - in a good way. That's because there's a dog sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for dog boarding on Rover? Check out our average dog boarding rates to get an idea before you start a conversation with a sitter.

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 Highwood Estates 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 Highwood Estates, 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 Highwood Estates, 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: