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.

Search Results

Confirmed availability: Labor Day
Katherine B.
Dogs are happiness 😊West Allis, WI, 53219
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Our 2 year old puppy had a great day and a good play date. I would highly recommend them and would definitely bring my pup here again! (more)

from
$50
per night
Calendar Recently Updated
Mj & James S.
Can't wait to meet your puppy dawg!West Allis, WI, 53227
Dog Boarding, Doggy Day Care

Gizmo seems to be quite happy with Jim snd Mary. Now this is very unusual for my baby. I will definitely book again with Mary and Jim. 10 stars!! (more)

from
$45
per night
Calendar Recently Updated
April & Brad R.
Opening home after losing petWest Allis, WI, 53214
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

The Richters were absolutely amazing! We received regular updates explaining what/how our Lola was doing, as well as pictures of the fun she was having. I was s… (more)

from
$50
per night
Confirmed availability: Labor Day
Jill F.
4.
Dog lover work from homeWest Allis, WI, 53214
Dog Boarding, Doggy Day Care

Jill did a great job with our Bonnie girl! She has a great house and fenced back yard for the pups and really cares about them! Bonnie had such a great time! (more)

from
$45
per night
Calendar Recently Updated
Mary G.
5.
I have a big fenced in yard and luvGreenfield, WI, 53228
Dog Boarding

We were so thankful to Mary for taking such good care of Angel. We adopted her during Covid so she had spent 18 months with only us. It was Christmas and we wan… (more)

from
$35
per night
Calendar Recently Updated
Ready to play and cuddleAlverno, Milwaukee, WI, 53220
Dog Boarding

Sooo happy to have found an awesome family to leave my lovable doggy with! Karen was great at letting me know with photos and updates while we were out of town… (more)

from
$28
per night
Calendar Recently Updated
7.
Every animal makes me smile!Bay View, Milwaukee, WI, 53207
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Blythe was a pleasure to work with and was a joy for my pup while on vacation. Blythe was very easy to work with and made me feel very comfortable, having not u… (more)

from
$35
per night
Calendar Recently Updated
8.
WAH Dog Lover - Nice suburban setupGreenfield, WI, 53219
Dog Boarding, Dog Walking

Tyler kept me updated throughout my dog’s stay. I could tell he cared about my dog and my dog was happy with him. (more)

from
$40
per night
Confirmed availability: Labor Day
9.
Dog lover and frequent sitterFairview, Milwaukee, WI, 53219
Dog Boarding, Doggy Day Care, Dog Walking

Scott was very wonderful with Gigi. Being a senior dog, she has different needs and he accommodated as I needed. He took her on lots of walks, sent a ton of upd… (more)

from
$65
per night
Confirmed availability: Labor Day
10.
Home 24/7 NO KennelingLincoln Village, Milwaukee, WI, 53215
Dog Boarding, Doggy Day Care

Carina took wonderful care of our dog. It was only the second time we had to leave her with strangers, she was a rescue and can be pretty nervous around folks s… (more)

from
$45
per night
Confirmed availability: Labor Day
11.
Warm, loving, home like suroundingsWest Allis, WI, 53219
Dog Boarding, Doggy Day Care

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 se… (more)

from
$35
per night
Calendar Recently Updated
12.
Liz 
Verified Enhanced Background Check
Rover 101
Former vet assistant, works at homeWest Milwaukee, WI, 53214
Dog Boarding, Doggy Day Care

Liz gave my snuggly and energetic 1 year old giant lots of love and attention. Her own dog is such a good and friendly playmate! I was out of town for a few day… (more)

from
$40
per night
Confirmed availability: Labor Day
13.
Loving and caring dog momWest Milwaukee, WI, 53214
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Mary took great care of our dog and took photos to boot, keeping us informed as to his stay. We will definitely be having Mary watch our dog again. (more)

from
$48
per night
Calendar Recently Updated
14.
Dog house that is people friendly!West allis, WI, 53214
Dog Boarding

Mandi and family were so wonderful for our high energy lab. They provided him with plenty of exercise, special treats/meals, and attention. Truly, they went abo… (more)

from
$35
per night
Pet love girl here at your service!West Allis, WI, 53227
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Jennifer is so friendly and really delights in my dog. She sends photo updates and treats my dog like I would. Very happy to have her watch my dog. (more)

from
$33
per night
Calendar Recently Updated
16.
Dog mom who loves all animals!Greenfield, WI, 53220
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Janice is the kind and caring person you can trust with your dogs! She watched our two dogs (one of which has special needs) for two days and our dogs loved he… (more)

from
$70
per night
17.
Pampered poochOak Creek, WI, 53154
Dog Boarding

Debbie took phenomenal care of my 4 year old German Shepherd. He is very needy and requires a tremendous amount of attention and stimulation. Debbie kept me wor… (more)

from
$50
per night
Calendar Recently Updated
18.
I have three great dogs and a fenceGreenfield, WI, 53228
Dog Boarding

Jill is awesome, very personable and our dog enjoyed her stay! She was also very professional and friendly will definitely recommend and use her again (more)

from
$30
per night
Confirmed availability: Labor Day
19.
Experience foster and dog sitter!Hales Corners, WI, 53130
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Eric did a fabulous job watching Sacha, or Shiba Inu/poodle mix dog. He provided updates at least twice a day, they included pictures of our dog. I would highly… (more)

from
$50
per night
Confirmed availability: Labor Day
20.
A fun, yet safe place for your pup!Washington Heights, Milwaukee, WI, 53208
Dog Boarding, Doggy Day Care

Very pleased with the service Deann provided. She took good care of my dog I loved the pictures she took. Excellent service job well done I will refer others. (more)

from
$35
per night

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: