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.
Dismiss
1. Julie

Dogs complete the family!

Wauwatosa, WI, 53226

Dog Boarding, Doggy Day Care

3 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)"

2. Daniela & Michael

Paws Down, the Best in Town!

Bay View, Milwaukee, WI, 53207

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

92 repeat clients

"Daniela was great with Ranger. We were so happy with her services. She treated him like her own and kept us updated throughout the week with pictures and h... (more)"

3. Melissa

Melissa's Comfort Zone

West allis , WI, 53227

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

10 repeat clients

"Maya is all tuckered out which means she had a great time! Melissa sent us pictures every day and was very easy to communicate with. We'll definitely be send... (more)"

4. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

4 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)"

5. Daniel

warm comfortable caring environment

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

19 repeat clients

"Balto and I are very happy to have met Dan and his lovely family! They took great care of Balto during this past weekend. I'm sure Balto is looking forward t... (more)"

6. Laura

Bleeding heart dog lover

Bluemound Heights, Wauwatosa, WI, 53213

Dog Boarding, Drop-In Visits, Doggy Day Care

2 repeat clients

"Badger had a nice stay with Laura! She was sweet to him and made him feel right at home with her dog. Hopefully he will be staying with her again soon. (more)"

7. Andrea

Wauwatosa's Wag More Motel

Wauwatosa, WI, 53213

Dog Boarding

8 repeat clients

About: Your dog will love it at the Wag More. My husband and I are self-employed giving me an extremely flexible schedule with plenty of time to pamper a... (more)

8. Andrea

Cavalier mom who loves animals

West Allis, WI, 53219

Dog Boarding, Doggy Day Care

1 repeat client

About: I have two Cavalier King Charles Spaniels and a cat, all little ladies. I also foster dogs and cats through local rescues. My dogs get along with a... (more)

9. Katherine

Reliable, devoted, diciplined.

Bay View, Milwaukee, WI, 53207

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

4 repeat clients

"I absolutely love Katherine! My dogs are never away from me and she was so understanding about that. My pups had a great time! I got pictures and even a vide... (more)"

10. Brian

Two Caregivers - Double the Love

Washington Heights, Milwaukee, WI, 53208

Dog Boarding, Drop-In Visits, Dog Walking

17 repeat clients

"Doggie's third stay with Brian! He is definitely one of Olive's official buddies in life! We continue to be thoroughly pleased with this dog sitting arrang... (more)"

11. Micha

Garden District Bed & Biscuit

Town Of Lake, Milwaukee, WI, 53207

Dog Boarding, Doggy Day Care, Dog Walking

3 repeat clients

"Micha, Nate, and Arya are remarkable! As a first time user of the service, I was not sure how Pepper would react to staying with a new family. Daily updates,... (more)"

12. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

10 repeat clients

"Dogs did soo well with Sandy! So thankful to find somewhere they can stay comfortably when we are gone. She was very accomodating and really appreciated she ... (more)"

13. April

Doggone Awesome Pet Sitting

West Allis, WI, 53219

Dog Boarding

8 repeat clients

"April had a great idea of a meet and greet prior to them watching the dogs. We were able to see the dogs in her environment which created a wonderful sense ... (more)"

14. Rachel

Long Walks and Lots of Play

Highwood Estates, Milwaukee, WI, 53219

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

"Rachel was an absolute gem of a find for our family! We have two large breed dogs, one of which requires medicine each am and one of which can be a challeng... (more)"

15. Jes

The Hardy-Berndt Ranch

Kensington, New Berlin, WI, 53151

Dog Boarding

28 repeat clients

"Daisy always has a great time. She is well cared for. (more)"

16. Kari

Best Friend Boarding

New Berlin, WI, 53227

Dog Boarding, Doggy Day Care

62 repeat clients

"Maple had a great time with Kari. She was very well cared for and was returned home safe and happy. Kari responds very quick to inquiries and sends picture... (more)"

17. Sarah

The Great Kind Of Dog House!!!

West Milwaukee, WI, 53215

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

6 repeat clients

"Sarah took a great deal of time making sure my pup was well-associated with her, her family, and her surroundings. She took excellent care of my dog and will... (more)"

18. Anastasia

Living in the dog house

West Allis, WI, 53214

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

About: After years of pet sitting for a large variety of families, I am excited to expand my clientele base. I have worked with dogs of all shapes and siz... (more)

19. Matthew

Dog dad, animal lover, adventurer

West Allis, WI, 53227

Dog Boarding, Drop-In Visits, Dog Walking

"Matt and his wife were great!!! They sent me picture of them out and about on walks and hikes and Spyder came home exhausted! Will definitely book Spyder t... (more)"

20. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

31 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)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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: