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.
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Daniela & Michael P.
Paws Down, the Best in Town!Bay View, Milwaukee, WI, 53207
House Sitting

Daniela did a wonderful job watching Chewie. When we were feeling anxious, she was so quick to respond with a photo of our happy pup. Highly recommend. (more)

from
$35
per night
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Travis H.
2.
Love & Exercise for your dog or catMartin Drive, Milwaukee, WI, 53208
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

We were thrilled when Travis agreed to watch our pup, Opi. Travis came over in advance to meet us and Opi. We knew he was a great match when he immediately gree… (more)

from
$40
per night
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Blythe R.
3.
Every animal makes me smile!Bay View, Milwaukee, WI, 53207
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Blythe was so wonderful with our senior Cavalier. Great communication and I came home to a spotless house and a happy well loved pup. I’d absolutely recommend h… (more)

from
$32
per night
Confirmed availability: Memorial day
Abigail L.
LOVE long walks more than your pup.Murray Hill, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking

Abigail was terrific: I found my kittens happy, joyous, and bounding about, she nicely documented everything they were doing and sent me photos and entertainin… (more)

from
$42
per night
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Meg M.
5.
Meg 
Verified Background Check
I love to walk and play with dogsAvenues West, Milwaukee, WI, 53233
House Sitting, Drop-In Visits, Dog Walking

Meg has frequently taken care of my two dogs and one cat. She is responsible and loving while caring for my pets. Meg has proven to be dependable, timely and … (more)

from
$35
per night
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6.
** Mission: meet ALL the dogs **Lower East Side, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking

Rachel went above and beyond house sitting my two pets for the week. When my dog had some unexpected stomach issues, she took great care of him and provided upd… (more)

from
$27
per night
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7.
Less talking more walking!Downer Woods, Milwaukee, WI, 53201
House Sitting, Drop-In Visits, Dog Walking

About: I am more than willing to walk your four legged friend around, check in on them, provide comfort and fun, and stay with them throughout the day or ni… (more)

from
$35
per night
8.
Neighbor providing additional loveJuneau Town, milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Jeremy was great with our dogs and our home. He encouraged play, comforted them, and ensured they were fed and watered appropriately. His intuition to our dogs … (more)

from
$33
per night
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9.
Experienced, reliable, retired!!!!!Historic Third Ward, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Laurie was so great with our puppy! I asked her very last minute too, she was very accommodating and send photo updates. Lovely lady, would definitely recommend… (more)

from
$50
per night
Confirmed availability: Memorial day
Your dogs second best friend.Riverwest, Milwaukee, WI, 53212
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jennifer was awesome! Super responsive, personable, and made sure to send picture updates of our happy pup. We had her stay in our house while we were gone and … (more)

from
$40
per night
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11.
I <3 furry friends & miss my fam’sLower East Side, Milwaukee, WI, 53202
Dog Boarding, House Sitting

Talor was amazing!!! Super responsive, personable, and made sure to send photo updates each day we were away. She was very attentive to our dog and made sure he… (more)

from
$30
per night
12.
I’ll run with your dog!Upper East Side, Milwaukee, WI, 53211
House Sitting, 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)

from
$40
per night
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13.
Dog lover with flexible scheduleYankee Hill, Milwaukee, WI, 53202
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Taylor always takes great care of our pups! Often when she sends us pictures of our dogs, they’re curled up next to her, so I can tell that they’re happy with h… (more)

from
$37
per night
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14.
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 up… (more)

from
$50
per night
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15.
Dog loverMurray Hill, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking

Emma was wonderful! She kept me updated the entire time. Kobe seem to stress free and I couldn’t be more grateful! (more)

from
$25
per night
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16.
WHO let the 🐕 🐩 🐕 dogs out ???!?Bay View, Milwaukee, WI, 53207
House Sitting, Drop-In Visits, Dog Walking

I have worked with Becca for many years. We are nurses. She is an extraordinary nurse which makes her an excellent pet caregiver. Since I have known Becca she… (more)

from
$45
per night
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17.
Pawesome, Detail-Oriented SitterCambridge Heights, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking

Our dog, Winnie, has separation anxiety issues, and Kaitlyn was incredibly accommodating and made Winnie feel comfortable while we went out for a few hours. Kai… (more)

from
$35
per night
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18.
caring for your pets through covid!Yankee Hill, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Hanna did a great job watching my dog, Rylee. She was flexible, quick to respond to messages and seemed genuinely excited about watching Rylee for a weekend...W… (more)

from
$35
per night
Confirmed availability: Memorial day
19.
Sam 
Verified Background Check
Rover 101
Loving and Reliable Housesitting.Juneau Town, Milwaukee, WI, 53202
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sam was great! Our dog started having medical issues right before we left and she took on the new adjustments no problem. We hope to use her again in the future… (more)

from
$40
per night
Calendar Recently Updated
20.
Your dog's "other" best friend!Harbor View, Milwaukee, WI, 53204
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Rachel was AMAZING! We had never used anyone besides friends/family to watch Rex so we were naturally a little leery. But she made it super simple! She came ove… (more)

from
$55
per night

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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 the Rover Guarantee, 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.