Dog Boarding in Hillside, Milwaukee

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

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Gabriel M.
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Sitter Profile Image: Gabriel M.
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1.

Gabriel M.

5 star treatment for your pet
Riverwest, Milwaukee, WI, 53212
1.9 mi. away
Boarding
5.0 out of 5 stars
18 reviews
8 repeat clients
from
$45
per night

I can't be thankful enough. He was not only perfect in taking care of my 8 month old puppy, he was flexible in timing as well if you want an ease of mind I do 100% recommend him.

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Sitter Profile Image: Blythe R.
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Sitter Profile Image: Blythe R.
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2.

Blythe R.

Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
4.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
137 reviews
61 repeat clients
from
$45
per night

My husband and I could not be more excited to have found Blythe as a sitter for our two needy pups! Not only was she flexible with us regarding our pick-up and drop off times, but she was SO understanding with our dogs’ specific needs. We have a very energetic & lovable pit bull named Roxy and a very ANXIOUS Vizsla-mix named Romeo. Blythe went above and beyond to keep Romeo calm while we were away, all while fulfilling Roxy’s needs for attention with daily brushing, cuddles and exercise. She kept us updated with photos and gave this worried puppy mom so much comfort to step away and enjoy our one year wedding anniversary weekend getaway! Thanks again Blythe! I know Roxy and Romeo are already looking forward to their next stay with you ???

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Sitter Profile Image: Kim S.
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Sitter Profile Image: Kim S.
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3.

Kim S.

Never lived a day without a pet
Glendale, WI, 53217
3.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
53 reviews
17 repeat clients
from
$45
per night

It was our dogs first time staying with Kim. She was very sweet with Watson. She took great care of him and sent daily pictures and updates. We will definitely book again!

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Sitter Profile Image: Rhonda G.
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Sitter Profile Image: Rhonda G.
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4.

Rhonda G.

Love to walk and cuddle.
Whitefish Bay, WI, 53217
4.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
84 reviews
38 repeat clients
from
$30
per night

Rhonda took very good care of Pickles. She sent lots of pictures. Took her on lots walks, and gave her a lot of attention. Very satisfied with the care Pickles received.

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Sitter Profile Image: Carina K.
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Sitter Profile Image: Carina K.
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5.

Carina K.

Big or small we love them all🥰
Lincoln Village, Milwaukee, WI, 53215
3.5 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
65 reviews
21 repeat clients
from
$45
per night

Carina did an awesome job watching my dog Bluto. She was very accommodating and gave lots of updates. She has a nice yard for pups to run around and a lovely daughter that enjoys playing with dogs. I would recommend her for any of your pup sitting needs.

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Sitter Profile Image: Brooke K.
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Sitter Profile Image: Brooke K.
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6.

Brooke K.

Loving your precious babies
West Allis, WI, 53227
6.7 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
31 reviews
17 repeat clients
from
$38
per night

Brooke was great! She sent many pictures and videos throughout the stay, and introduced her animals to my dog gradually to make sure they were all comfortable with each other. Extremely responsive and flexible. My dog came home healthy and happy!

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Sitter Profile Image: Cade & Jillian F.
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Sitter Profile Image: Cade & Jillian F.
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7.

Cade & Jillian F.

My girlfriend and I love dogs!
Kilbourn Town, Milwaukee, WI, 53203
0.5 mi. away
Boarding, Doggy Day Care, Dog Walking
2 reviews
from
$30
per night

Cade has a genuine love for animals. He is trustworthy, reliable and professional. He will go above and beyond to make sure your pet is comfortable and loved!

Confirmed availability: Easter Weekend
Sitter Profile Image: Hannah R.
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Sitter Profile Image: Hannah R.
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8.

Hannah R.

Lover of furry friends!
Riverwest, Milwaukee, WI, 53212
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
47 reviews
10 repeat clients
from
$35
per night

Hannah and her family were great host for our dog son! Anubis is very energetic for his size and has some anxiety but it seems they took really good care of him. At pick up, Anubis was very happy and healthy! Thank you very much, we will use Hannah again!

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Sitter Profile Image: Connor M.
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Sitter Profile Image: Connor M.
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9.

Connor M.

Miss my own dog so now I’m here :)
Lower East Side, Milwaukee, WI, 53202
0.8 mi. away
Boarding
5.0 out of 5 stars
3 reviews
from
$35
per night

Simba had a blast and Connor was great about updating me over the weekend on how he was doing!

Sitter Profile Image: Alli M.
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Sitter Profile Image: Alli M.
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10.

Alli M.

Your dog will have a new bestfriend
Lower East Side, Milwaukee, WI, 53202
1.6 mi. away
Boarding, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$35
per night

Alli did a great job taking care of our little Zoe!

Confirmed availability: Easter Weekend
Sitter Profile Image: Kathy & Brad K.
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Sitter Profile Image: Kathy & Brad K.
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11.

Kathy & Brad K.

Your Dog's Home Away from Home
Greendale, WI, 53129
8.4 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
37 reviews
15 repeat clients
from
$40
per night

Kathy and Brad were so wonderful! They sent lots of photos throughout Rosie’s stay. Love that they only accept one pet at a time. Will definitely book again! :)

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Sitter Profile Image: Alberto V.
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Sitter Profile Image: Alberto V.
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12.

Alberto V.

Rover 101
Welcome to our home 🤍🏡
Historic Mitchell Street, Milwaukee, WI, 53204
3.1 mi. away
Boarding
5.0 out of 5 stars
25 reviews
7 repeat clients
from
$33
per night

Highly recommend! Alberto and Chance were both super friendly and kept me updated throughout my trip! Definitely made me feel secure and safe about leaving my pup throughout the weekend:-)

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Sitter Profile Image: Emily V.
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Sitter Profile Image: Emily V.
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13.

Emily V.

Caring, active, & attentive sitter
Brewer's Hill, Milwaukee, WI, 53212
0.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
2 reviews
from
$25
per night

I have trusted Emily to watch my dog many times over the past few years. She loves animals and is very caring and thoughtful! She is responsible, reliable and makes safety a priority. My dog loves when she gets to spend time with her!

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Sitter Profile Image: Dominic S.
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Sitter Profile Image: Dominic S.
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14.

Dominic S.

Dog walker/Home Visits
Lower East Side, Milwaukee, WI, 53202
1.0 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$38
per night

About: I have two dogs both around 2 years old and have had them since they were puppies. I love dogs and would love to help and others and be able to meet some more puppies! I work from home, but I am free anytime before 9 am, 11:30-12, and anytime after 5pm. If live close by, I could make a quick stop by during the work day as well. Along with treating your dog as one of my own, I can also bring over my maltipoo who has tons of energy and loves to play with other dogs.

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Sitter Profile Image: Karen & Toy
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Sitter Profile Image: Karen & Toy
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15.

Karen & Toy

Rover 101
Ready to play and cuddle
Alverno, Greenfield, WI, 53220
6.0 mi. away
Boarding
5.0 out of 5 stars
79 reviews
39 repeat clients
from
$35
per night

This family is truly amazing. They gave daily updates and took great care of my dog. They even bought him a halloween costume. Will be booking again! :)

Confirmed availability: Easter Weekend
Sitter Profile Image: Liz P.
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Sitter Profile Image: Liz P.
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16.

Liz P.

Pet Lover who works from home!
Riverwest, Milwaukee, WI, 53212
2.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
35 reviews
18 repeat clients
from
$40
per night

Liz is super sweet. I felt very comfortable letting her watch and take care of my cat. She was very flexible with me when I was running late. She sent pictures throughout my cat’s stay.

Sitter Profile Image: kiki A.
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Sitter Profile Image: kiki A.
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17.

kiki A.

Animal lover & nurturer
Silver Spring, Milwaukee, WI, 53218
6.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$30
per night

We had the pleasure of having Kiki watch over our beloved Kody during Thanksgiving break, and we couldn’t be more impressed and her for the exceptional care she provided. Kiki’s genuine love for animals shines through in every interaction with Kody. Her attention to detail, reliability, and warmth created an environment where Kody not only felt comfortable and safe but genuinely happy. Kiki went above and beyond ensuring we had photos his ever loving personality during his time with her.🐾 We are incredibly thankful for Kiki’s outstanding service and wholeheartedly recommend her to anyone seeking a reliable and caring pet sitter.

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Sitter Profile Image: Daniel & Holly L.
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Sitter Profile Image: Daniel & Holly L.
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18.

Daniel & Holly L.

Rover 101
Warm, loving, home like suroundings
West Allis, WI, 53219
4.8 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
378 reviews
159 repeat clients
from
$38
per night

Dan and Holly were great! We took a four day vacation recently. Our Ralph is a rescue and has never spent any time away from us since we got him so we were worried about how he would do. We did a meet-and-greet beforehand so our rather clingy pup could get to know them and their two dogs. We could tell immediately how much they love animals. Our dog had a good time and was totally wiped out when we picked him up which was good because so were we. If we travel again, we will use Dan and Holly.

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Sitter Profile Image: Amanda & Cody T.
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Sitter Profile Image: Amanda & Cody T.
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19.

Amanda & Cody T.

We love dogs! Come meet us!
Historic Third Ward, Milwaukee, WI, 53202
1.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
27 reviews
10 repeat clients
from
$45
per night

Cody & Amanda took such great care of my Josie! Lots of pictures and very communicative. Highly recommended and I will be back in the future 😊

Confirmed availability: Easter Weekend
Sitter Profile Image: Sarah J.
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Sitter Profile Image: Sarah J.
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20.

Sarah J.

I’m awkward with humans.
West allis, WI, 53219
6.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
94 reviews
31 repeat clients
from
$25
per night

I couldn’t have asked for a better puppy sitter for our Baylee! Sarah took the extra time to come visit us before our boarding date so Baylee would see a familiar face. Baylee got to experience being around other dogs and cats while in her home which I hoped would be a super fun weekend for her and it sounded like it was based on the updates Sarah gave during Baylee’s time with her. Our pup isn’t fully potty trained and there were no issue there, Sarah was super understanding of that. If we need a sitter in the future we will definitely reach out to Sarah first and foremost 🙂

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Rover also offers Dog Boarding in these neighborhoods:

Rover also offers other services in Hillside:

Pet parents turn to sitters on Rover.com when they're looking for overnight boarding for their dog. 1089 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:

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