House Sitting in Oakwood Village, Madison, WI

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.

Search Results

Calendar Recently Updated
Andrew L.
1.
COVID SAFE 24/7 online Vet accessGreenbush, Madison, WI, 53715
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

“Uncle” Drew loved our girl while we were away. She went on walks, car rides, puppy play dates, cuddled on couches and got treats. Drew sent us pictures every d… (more)

from
$80
per night
Calendar Recently Updated
Ruthanne F.
I pawsitively love dogs and cats!Old Middleton Greenway, Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking

Ruthanne was great with my little 2 Chihuahua mixes! She is such a "Dog" person, which made me feel more comfortable to have her sit them. She played with them … (more)

from
$45
per night
Calendar Recently Updated
Camille M.
Outgoing, student, dog loverMiddleton, WI, 53562
House Sitting, Drop-In Visits, Dog Walking

Camille did an amazing job watching our older dog who is finicky and very particular about food, walks, and sleep while we were gone overnight for a few days. S… (more)

from
$35
per night
Calendar Recently Updated
Cheyenne K.
Expert and Loving Animal CaretakerBurr Oaks, Madison, WI, 53713
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

This was our first over night with Cheyenne, so I thought I would write another review. Our dog is very hesitant and skittish with people. Cheyenne is very help… (more)

from
$80
per night
Kate K.
5.
Cared for as if you were homeMiddleton, WI, 53562
House Sitting, Drop-In Visits

Kate took wonderful care of our elder dog with special needs. She spent a week at our house, and sent updates to let us know how he was doing. She also took gre… (more)

from
$45
per night
Calendar Recently Updated
6.
Home is where the bark isFitchburg, WI, 53711
House Sitting, Drop-In Visits, Dog Walking

Robert did such a great job watching my two dogs at my house for a long weekend. He was kind, neat, friendly, patient, conscientious and very attentive to anyth… (more)

from
$28
per night
Calendar Recently Updated
7.
Energetic lover 🥰 of Fur-babies!Middleton, WI, 53562
House Sitting, Drop-In Visits, Dog Walking

Donna was wonderful with our pets - a dog and a cat. She was also great with our home and really put us at ease, as this was the first time we brought someone i… (more)

from
$45
per night
Calendar Recently Updated
8.
Love is a four legged wordMadison, WI, 53713
House Sitting, Drop-In Visits, Dog Walking

Linzi did a great job taking care of all my animals. She went above and beyond and I couldn't be happier with her. She communicated all weekend. I was able to h… (more)

from
$35
per night
Calendar Recently Updated
9.
Your dog's new bestie!Madison, WI, 53717
House Sitting, Drop-In Visits, Dog Walking

Sara was fantastic with our last minute request. We felt not only comfortable, but that the dogs would be having a fun time with Sara there! Great pictures an… (more)

from
$50
per night
Calendar Recently Updated
10.
Trained 12+ dogs. Enjoy walksWesthaven Trails, Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking

I was originally terrified to leave my dogs with a stranger as well as in my house without someone there but Lucas completely put me at ease. I do have cameras … (more)

from
$35
per night
Calendar Recently Updated
11.
The Best Care For Your Companion!Meadowood, Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking

Carissa is GREAT with my pups. Always shows up, sends updates, and they’re always healthy and happy when we return. :). Recommend to anyone. (more)

from
$50
per night
Calendar Recently Updated
12.
Fun, energetic dog sitter & boarderMadison, WI, 53719
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Emily took excellent care of our two dogs while we were away and we are looking forward to having her and her sweet dog Belle come house sit for us again! (more)

from
$35
per night
Calendar Recently Updated
13.
Liz 
Verified Enhanced Background Check
Current UW Veterinarian StudentMiddleton, WI, 53562
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Liz did a wonderful job taking care of my cats! She was an excellent communicator while I was gone, sending texts and photos daily. She handled the meds and sub… (more)

from
$50
per night
Calendar Recently Updated
14.
Incoming college freshman dog loverHigh Point Estates, Madison, WI, 53719
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Bella did a great job house sitting my dog! She kept him safe and happy the whole week were out of town. Thanks Bella! (more)

from
$45
per night
Very Active, Fun, Playful, love allAllied Community, Fitchburg, WI, 53711
House Sitting, Drop-In Visits, Dog Walking

Nicholas was phenomenal with Kane. He played with Kane. He made Kane felt like he was part of his family. He updates my husband and I with details throughout th… (more)

from
$50
per night
Calendar Recently Updated
16.
BIG dog personSkyview Meadows, Madison, WI, 53719
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Molly is friendly, timely, and provided exactly the care we desired for our pup Milo! She was prompt in all communications and flexible, which was so helpful. W… (more)

from
$35
per night
Calendar Recently Updated
17.
Daily visits to the dog park!Marbella, Madison wi, WI, 53705
House Sitting, Drop-In Visits, Dog Walking

Clara loves dogs and has been around them her entire life! She is a responsible pet owner herself to an adorable German Shepard. She enjoys walking, playing a… (more)

from
$75
per night
18.
Love walks and love dogs!Spring Harbor, Madison, WI, 53705
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I appreciate that Lauren was very attentive asked questions and texted me pictures I came home to find the dogs calm and tired so they obviously had a good walk… (more)

from
$50
per night
Calendar Recently Updated
19.
Dog owner & med student!Spring Harbor, Madison, WI, 53705
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sophie watched my dog, Ava, multiple times throughout this past fall and she did an amazing job each time. I was interviewing for medical schools and so I would… (more)

from
$30
per night
20.
Easygoing pet lover in grad schoolMadison, WI, 53711
House Sitting, Drop-In Visits

Bree went above and beyond to make sure our cats were as comfortable as possible during a very stressful time for them. She was communicative and responsive the… (more)

from
$70
per night

When it comes to pet care and house sitting, pet owners in Oakwood Village, Madison, WI trust their pets with sitters on Rover.com. Over 423 pet owners have reviewed house sitters in Madison, giving them an average rating of 4.9/5. House sitting doesn't have to be expensive. In fact, it's probably a lot more affordable than you think. You'll quickly find that there's a house sitter on Rover for just about every price range and lifestyle. Wondering how much you might expect to pay for a house sitter and pet care on Rover? Check out our average house sitting rates to get an idea before you begin a conversation with a sitter who seems like a great match.

Never beg a friend to watch your dog again. With Rover, you can find your the perfect Oakwood Village house sitter in seconds. When you book house sitting on Rover, your dog will enjoy a loving, relaxing stay in their own home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers care for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach trusted house sitters in Oakwood Village, Madison who can provide the care your dog needs, when they need it.

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 Oakwood Village, Madison 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 Madison.

We're proud to support over 200 organizations across the nation, including: