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House Sitting in Milwaukee

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed availability
4th of July
1. Samantha

Sam's Dog Days

Yankee Hill, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Samantha is a dream. She's very personable and great with communication. I'd recommend her to anyone. (more)"

Confirmed availability
This weekend
2. Danielle

Full time house/dog sitter!

Whitefish Bay, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

"Danielle did a fantastic job watching my dog while I was out of town. She kept me updated during her stay, and I came home to a well-exercised, contented dog... (more)"

Confirmed availability
4th of July
3. Savannah

Dog lover for hire!

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Savannah is a very capable and mature individual who is very good with both animals and people. She commits and works well in many environments. (more)"

Calendar Recently Updated
4. Taylor

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

House Sitting

"I'm so used to giving the, "one of my dogs has been abused and you need to let her come to you speech," when in walks Taylor and my struggling pup runs right... (more)"

Calendar Recently Updated
5. Tasha

Your dog’s next bff!

Glendale, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Tasha was awesome with our dog! She came organized and prepared to our meet and greet with important questions about Gus. She was patient and did great helpi... (more)"

Calendar Recently Updated
6. Sarah

Taking myself for walks gets boring

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Sarah is amazing. She was so great with my puppy, sent me photos while I was away, very accommodating to my schedule, would definitely recommend to anybody w... (more)"

Confirmed availability
4th of July
7. Erin

Flexible hours!!!

Upper East Side, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Erin is awesome! My dog Ruby was a very happy girl in her care. (more)"

Calendar Recently Updated
8. Vanessa

Lots of TLC

Burnham Park, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"Vanessa was so good with my dog! She did everything right and stayed in close contact with me. I would hire her again for a future stay. (more)"

Confirmed availability
4th of July
9. Amanda

Happy Paws make for Happy Owners!

Johnson's Woods, Milwaukee, WI, 53214

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

"Amanda stayed at my home as a house-sitter my little dog who suffers from separation anxiety. Buff, who is normally very hostile to strangers attached herse... (more)"

Calendar Recently Updated
10. Gwenn

I love all dogs equally.

Walker's Point, Milwaukee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

"Gwenn was awesome!! I've got a crazy household including a special needs blind pup, an old guy that that has a tough time getting around and a wild child att... (more)"

Calendar Recently Updated
11. Ashlyn

I'll exceed your pet's needs

Northpoint, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Ashlyn and Chris are the most accommodating and gentle sitters. Our dog adores them. They are the best. (more)"

Calendar Recently Updated
12. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

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

"Lori stayed overnight at our house during the week we were overseas. She sent us pictures every day and worked with my mom and sister to manage the dogs (we ... (more)"

Calendar Recently Updated
13. Olivia

Animal Behavior Master's Student

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Olivia was the perfect fit for us and our pets. She was an excellent communicator, kept us updated, and made sure our animals were happy and taken care of wh... (more)"

Calendar Recently Updated
14. Abbey

Flexible, responsible, animal lover

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Abbey did a great job!!! She was confident about what she was doing and really good about paying attention to everything that we told her. We felt very at ea... (more)"

Calendar Recently Updated
15. Laurie

Experienced, reliable, retired!!!!!

Historic Third Ward, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Upon meeting Laurie for the first time, my husband & I felt incredibly comfortable having her care for our pups in our home!!! During our meet & greet Laurie... (more)"

Calendar Recently Updated
16. Colleen

Walks, Runs, and Belly Rubs.

Avenues West, Milwaukee, WI, 53233

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

"Colleen is an amazing dog sitter. I have a 1 1/2 year old rescue dog who is scared of all strangers. It takes him a VERY long time to trust strangers. Col... (more)"

Confirmed availability
4th of July
17. Alexis

Dogs are my passion!

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Alexis is AMAZING with caring for and watching over your furry companions. I can always count on her for bookings and know that a good job will be done. She ... (more)"

18. Caitlin

Run, walk, play with dogs!

Northpoint, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"When I adopted my dog Oliver, he fell in love with Caitlin immediately. I went to go pick him up and she went with me as this is both an exciting and nerve w... (more)"

19. Brian

I'll exercise and take care of dog

Upper East Side, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Brian has had dogs in his life since he’s been born and it doesn’t surprise me he’s wanting to work with dogs! He trained both of our labs and took them to ... (more)"

20. Taylor

Full-time Pupper Lover

Juneau Town, Milwaukee, WI, 53202

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

"Taylor has had a dog her whole life. She is a responsible young adult who’s love of all animals makes her one of the best caregivers. She has been responsibl... (more)"


Rover.com is the simple, savvy way to find and book Cold Spring Park, Milwaukee 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 Cold Spring Park 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 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 Cold Spring Park, Milwaukee, WI house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.