House Sitting in Hillside, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

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1. Travis Verified Background CheckRover 101

Love & Exercise for your dog or cat

Martin Drive, Milwaukee, WI, 53208

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

"Travis was great! My dogs are not used to being left and they were very happy and comfortable with him watching them. Would definitely book again! (more)"

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2. Niamh Verified Background Check

Available to help through Covid!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Niamh was so great!! Couldn’t have picked a better person to come to our house for the weekend while we were away to watch our high energy boy. Kept us fully u… (more)"

Confirmed availability
 Easter weekend
3. Abigail Verified Background CheckRover 101

LOVE long walks more than your pup.

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Abigail did a great job. She came over to my house the night before to meet the dogs. And it was a really good experience. Thank you Abigail (more)"

Confirmed availability
 Easter weekend
4. Colleen Verified Background CheckRover 101

Snuggles, Walks and Treats

Whitefish Bay, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Colleen was absolutely fantastic and took all of the stress out of leaving our dog behind while going on vacation. Usually he’s left with family and when we re… (more)"

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5. Rachel Verified Background Check

** Mission: meet ALL the dogs **

Lower East Side, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"I can't say enough about how great Rachel is! Bunnies are very hard to care for, and she does it at an all-star level. We came home to clean, happy bunnies an… (more)"

Confirmed availability
 Easter weekend
6. Isabella Verified Background Check

Your Pet's New Best Friend

Downer Woods, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Isabella is a very caring and responsible person. She loves dogs and will be a great dog walker for your dog! I definitely recommend her! (more)"

7. Sadie Verified Background Check

I’ll run with your dog!

Upper East Side, Milwaukee, WI, 53211

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

"Sadie was was good with Brodi. Other than being 15 minutes late I think she did a good job of keeping my Brodi happy. I will use her services again. (more)"

8. Tasha Verified Background CheckRover 101

Your dog's next BFF!

Shorewood, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Tasha was awesome. This was my first time leaving my dogs overnight with someone who wasnt family. The best thing was to s3 them looking happy in the photos sh… (more)"

Confirmed availability
 Easter weekend
9. Jennifer Verified Background Check

Your dogs second best friend.

Riverwest, Milwaukee, WI, 53212

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

"We loved Jennifer and our dogs loved her as well. (more)"

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10. Rachel Verified Background CheckRover 101

Pet care you can trust.

Lower East Side, Milwaukee, WI, 53202

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

"Rachel is reliable, hard working, and most importantly, GREAT with dogs. She has taken care of many types of dogs; large, small, scared, energetic, you name it… (more)"

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11. Maisie Verified Enhanced Background CheckRover 101

Hard-working animal enthusiast!

Lower East Side, Milwaukee, WI, 53202

House Sitting

"Great dog sitter. She was great with communication and with the two dogs. (more)"

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12. Jessica Verified Background Check

Attentive Careful and Kind Sitter

Cambridge Heights, Milwaukee, WI, 53211

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

"Great updates! She did a greatjob (more)"

13. Christina Verified Background Check

Welcome dog owners!

Cambridge Heights, Milwaukee, WI, 53211

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

"Christina was excellent. Not only was she great with our dog, she even made sure the house was kept extremely clean. She was also nice enough to clean up after… (more)"

Confirmed availability
 Easter weekend
14. Rachel Verified Background CheckRover 101

Your dog's "other" best friend!

Harbor View, Milwaukee, WI, 53204

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

"Rachel house sitted for me this time while taking care of my American Bulldog. Rachel has always been amazing with Ernie and knowing she was watching the house… (more)"

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15. Katie Verified Enhanced Background Check

Riverwest staycation for dogs!

Harambee, Milwaukee, WI, 53212

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

"Whadda gem! We’re super happy we found Katie. Our little guy has a temporary medical issue and cannot be around other dogs. So daycare is out and we found ours… (more)"

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16. Hailey Verified Enhanced Background Check

Your Pets are my Passion!

Juneau Town, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"I booked Hailey at the last minute to house sit and to sit for my dog and she did such an amazing job!!! She sent me pictures and communicated with me daily wh… (more)"

17. Jeremy Verified Background CheckRover 101

Neighbor providing additional love

Juneau Town, milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"I cannot recommend Jeremy enough. He is easy to work with, thoughtful and considerate, and has a wonderful way with dogs. We were concerned that our red heeler… (more)"

18. Alyssa Verified Background Check

Care for your furry or scaly friend

Northpoint, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Alyssa was seriously the best sitter we’ve ever had! Our dog, Lea, loved her! We came back to a very happy dog. House and everything was just as we left it. Wi… (more)"

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19. Emily Verified Background Check

Caring & Active Dental Student

Avenues West, Milwaukee, WI, 53233

House Sitting

"Emily did a great job watching our dogs while we went to the cabin for the weekend. She came across as very warm, genuine, and caring when we first met her. … (more)"

20. Taylor Verified Background Check

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

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

"Taylor was great! She was very respectful of the house and gave me great updates about my dog and cat. I will be using her in the future and you should too! My… (more)"

Pet parents in Hillside, Milwaukee, WI love dog sitters on Rover.com. 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Hillside house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Hillside, Milwaukee, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Hillside house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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: