Dog Boarding in Highwood Estates, Milwaukee

Find a loving dog sitter to watch your dog overnight at your sitter's home.

Available this weekend
1. Daniel

warm comfortable caring environment

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

34 repeat clients

"Dan and his family were amazing with our dogs. We were receiving a daily update of how they were doing and lots and lots of photos and videos It was great to... (more)"

2. Melissa

Melissa's Comfort Zone

West allis, WI, 53227

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

23 repeat clients

"Melissa was great! Rascal was well cared for and happy when we picked him up. We have already planned for Rascal to stay with Melissa again next month. (more)"

3. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

22 repeat clients

"Bear had a great stay. Brian and Becky were great. Their house was clean and set up to be all about dogs. I will continue to use them for Bear's walk and fut... (more)"

4. Julie

Dogs complete the family!

Wauwatosa, WI, 53226

Dog Boarding, Doggy Day Care

8 repeat clients

"Charlie loved staying with Julie! She was so good to him- tons of snuggles and pats-and he loved playing with her lab as well. He was happy and tired after a... (more)"

5. Julie

Large fenced yard and a Lab buddy

Wauwatosa, WI, 53213

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

2 repeat clients

"Julie and her family were great with Kaiser! I think he really enjoyed having a pack to stay with while we were gone. I loved Julie's updates too! I'm so gla... (more)"

6. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

14 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)"

7. Dana + Justin

Fenced in yard-bring to work!

Town Of Lake, Milwaukee, WI, 53207

Dog Boarding, Doggy Day Care

1 repeat client

"Ranger had a great stay with Dana, Justin and Millie! They went hiking together and played in the back yard. Would recommend and will be returning! (more)"

8. Andrea

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

9 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)"

9. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

7 repeat clients

"Valeria watched our dog Otis for 10 days while we were on a long vacation. She gave us regular updates and photos which was so good to see while we were away... (more)"

10. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

38 repeat clients

"Kathleen did an awesome job. She even sent me pictures of my baby Princess everyday. She was also very nice and I can tell she really loves dogs! I would def... (more)"

Available this weekend
11. katie

K&A's Doggie Retreat

Greenfield, WI, 53228

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

1 repeat client

"Roscoe enjoyed his time with Katie and the other dogs. He was well taken care of and came home cleaner than when he left! (more)"

12. Andrea

Cavalier mom who loves animals

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

4 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)"

13. Sandy

Home full-time. Love all dogs!

Greenfield, WI, 53220

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

2 repeat clients

"Sandy has taken such good care of Buddy. This was our 2nd time using her. She had him for 2 weeks this time while I was out of the country! She sent lots of ... (more)"

14. Sarah

The Great Kind Of Dog House!!!

West Milwaukee, WI, 53215

Dog Boarding, Drop-In Visits, Doggy Day Care

10 repeat clients

"Sarah and her family were wonderful! They took care of Charlie like he was their own while we went out of town for three days. We received regular updates an... (more)"

15. Denise

Simply Love Dogs!

West Allis, WI, 53214

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

About: I love dogs, like everybody on here! I enjoy long walks and taking my dogs to the dog parks and swimming. Big believer that dogs need friends, and... (more)

16. Tracie

Peace Of Mind With Private Care

Johnson's Woods, Milwaukee, WI, 53214

Dog Boarding, Doggy Day Care

9 repeat clients

"Tracie was friendly and my dog had a great time at his stay. Tracie was accommodating when our pick up time changed and communicated with us throughout our ... (more)"

17. Robyn

Two care givers to spoil your pup

Cannon Park, Milwaukee, WI, 53226

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

"Robyn was very responsive and flexible. She provided us with picture updates such that I knew my goldendoodle was having a great time. Would recommend and pl... (more)"

Available this weekend
18. Sylvia

Very excited to care for your dog!

Fairview, Milwaukee, WI, 53219

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

"Sylvia was an amazing sitter to our little Baxter. She has sat for us twice and Baxter was so excited to see her both times. He could feel the love she has ... (more)"

19. Chandler

Obsessed with dogs since '93

West Allis, WI, 53227

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

"Chandler has watched my dogs on many occasions and is very accommodating to my dogs needs. My dog always comes home exhausted so I know she was very active d... (more)"

20. Sheila-Ann

Sheila-Ann S.'s Home

west allis, WI, 53227

Dog Boarding, Dog Walking

About: Hello everyone! My name is Sheila I have been watching dogs since I was 16 years old. It's my passion my life I love all dogs no matter breed sha... (more)

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Learn About Premier

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: