House Sitting in Oakwood Village, Madison, WI

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Louisa M.
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Sitter Profile Image: Louisa M.
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1.

Louisa M.

Your pet’s new friend! 🐶🐱🐰🐔🐠
Midvale Heights Community, Madison, WI, 53711
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
31 reviews
12 repeat clients
from
$60
per night

Louisa stayed in our home to watch our dog and two cats. She sent us sweet and thoughtful updates and we felt very confident that our animals were well taken care of! Would definitely book her again.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Maggie P.
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Sitter Profile Image: Maggie P.
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2.

Maggie P.

Young professional who loves pets!
Tenney-Lapham, Madison, WI, 53703
House Sitting, Drop-In Visits, Dog Walking
5.0
8 reviews
2 repeat clients
from
$35
per night

Maggie is wonderful! She did a meet and greet with my two dogs before she stayed the weekend with them. She was great with communication and took excellent care of my girls. I will definitely continue to book her. Highly recommend!

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Sitter Profile Image: Sara J.
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Sitter Profile Image: Sara J.
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3.

Sara J.

I’ll take care of your PAWfect pup
Junction Ridge, Madison, WI, 53717
House Sitting, Drop-In Visits, Dog Walking
5.0
14 reviews
4 repeat clients
from
$65
per night

This was the first time I've used Rover and found Sara. Communication was great from the get-go. As this was the first time I let someone else watch Iris (8 months old), rightfully so to be nervous and hesitant. Sara was very understanding and attentive as I went through what Iris needed, how her demeanor is, and all of the in-between. You could tell that Sara genuinely cares and enjoys caring for pets as a side gig. Sara was fantastic and we'll definitely book again.

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Sitter Profile Image: Denae B.
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Sitter Profile Image: Denae B.
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4.

Denae B.

We're walkin, talkin, soakin up sun
Fitchburg, WI, 53711
House Sitting, Drop-In Visits, Dog Walking
5.0
17 reviews
7 repeat clients
from
$40
per night

Denea was amazing. We were a bit worried about one of our two dogs being anxious around strangers. But Oreo welcomed Denea and cuddled right up to her. We hope to continue using her in the future.

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Sitter Profile Image: Jess B.
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Sitter Profile Image: Jess B.
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5.

Jess B.

Your weekend/evening needs covered!
Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking
5.0
25 reviews
8 repeat clients
from
$85
per night

Jess was very friendly and willing to work with our difficult dog (and show equal love to our not-as-difficult dog!) She was also great communicating with us before and during the stay, and took good care of our pup and house.

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Sitter Profile Image: Briana L.
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Sitter Profile Image: Briana L.
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6.

Briana L.

Love to cuddle and spoil your pets
Meadowood, Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking
5.0
13 reviews
5 repeat clients
from
$30
per night

Thanks again! Briana stepped in at the last minute when we needed to leave town for a funeral. She took good care of Frankie. We’re grateful.

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Sitter Profile Image: Andrew L.
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Sitter Profile Image: Andrew L.
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7.

Andrew L.

Rover 101
Looking for a fur baby to love! 💜
Madison, WI, 53726
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
103 reviews
45 repeat clients
from
$89
per night

“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 day of special outings, and cuddles. We missed her so much but we knew she was being cared for and loved while we were away. Through text exchange, drew told us things about our girl that only someone who was invested in her would pick up on. We feel so grateful to have found Drew and will definitely ask him to take care of her again!!

Sitter Profile Image: Taylor R.
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Sitter Profile Image: Taylor R.
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8.

Taylor R.

Professional fury baby spoiler!
Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking
5.0
19 reviews
4 repeat clients
from
$65
per night

Taylor always takes fantastic care of our boys! We have hired her 3 or 4 times now and are just so happy we have found someone we can trust with our dogs!

Sitter Profile Image: Erin N.
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Sitter Profile Image: Erin N.
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9.

Erin N.

Lifelong Pet Owner & Biologist
Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$40
per night

My dog loved being spoiled by Erin. Erin is super responsible, organized, and took great care of my dog, from walks, feeding, medicine, etc. She loves animals and is very experienced!

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Sitter Profile Image: Shaina N.
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Sitter Profile Image: Shaina N.
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10.

Shaina N.

Animal-loving Madisonian
Midvale Heights Community, Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking
5.0
3 reviews
1 repeat client
from
$75
per night

Hello it is with great pleasure that I provide this reference for Shaina. It is rare that you will find someone who is so dedicated to the health and safety of all animals. She is that person who stops on the road to pick up an abandoned bird and locate help She has a vast amount of experience taking care of all types of animals with dogs and cats being the most common. She has many times given our pets medication‘s and special food with no problem at all. She is very responsible and punctual. I think she would be a great asset to anybody’s furry family. I highly recommend her as an animal caretaker.

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Sitter Profile Image: Alisyn L.
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Sitter Profile Image: Alisyn L.
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11.

Alisyn L.

Veterinary Technician & Adventurer
Walnut Grove, Madison, WI, 53717
House Sitting, Drop-In Visits, Dog Walking
5.0
27 reviews
13 repeat clients
from
$60
per night

Alysin is an amazing pet sitter, and I don’t say that lightly! We understand that we have quite the needy/special bunch, and she took care of them and our home as if they were her own. She’s an awesome communicator about what’s going on while we’re away, and pays great attention to every detail. We commented to each other how it was so nice that we didn’t feel any worry while on vacation with her taking care of our pack. Our animals love her, and we will definitely book with her again in the future! Thank you, Alysin!

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Sitter Profile Image: Samantha S.
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Sitter Profile Image: Samantha S.
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12.

Samantha S.

Dedicated doggo lover
Verona, WI, 53593
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
15 years of experience
from
$35
per night

About: I’ve taken care of dogs since I was in my early 20s. I grew up with dogs, my entire life, including shelties and beagles. When I was in my early 20s, I adopted my first dog! After she passed, I started volunteering with Midwest beagle rescue and have fostered several beagles through them. I enjoy spending time with dogs and getting to know their individual personalities. My favorite types of dogs are seniors. I just love to give them all of the love that I possibly can, and have a lot of patience in dealing with their special needs. I am currently a remote employee and have lots of flexibility throughout the week. Pet care fits into my schedule and the way that it works best for you and your pet. I have a nice dog park near my house, as well as a fenced in area in my complex. I’m happy to take your dog on walks and have lots of experience with challenging beagles/runners! My home is clutter free and the resident cat is friendly with all pets. I’m happy to come to your home as well. When in someone else’s home, I try to leave it just the way I left it. The last thing that I want is you coming home to something unexpected.

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Sitter Profile Image: Cory D.
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Sitter Profile Image: Cory D.
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13.

Cory D.

Unleash the Ultimate Peace of Mind
Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking
5.0
14 reviews
2 repeat clients
from
$50
per night

Corey was the best dog sitter by far! He sent updates so I knew he was there with them. He even deep cleaned our kitchen! He was so good to the dogs as well! We will definately hire him again!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Seán & Leticia W.
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Sitter Profile Image: Seán & Leticia W.
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14.

Seán & Leticia W.

Take Care Of Your Best Friend!
Maple-Prairie, Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking
5.0
4 reviews
1 repeat client
from
$27
per night

I’ve know Seán for a few years now, and ever since I’ve know him he always talks about his dog Penny. He is an awesome dog dad. He is excellent with dogs, I’ve seen him interact with dogs and he absolutely great with dogs. I would %100 trust Seán with my dogs Bean & Dotty. You have my word that your dogs will be in good hands with Seán.

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Sitter Profile Image: Stephany D.
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Sitter Profile Image: Stephany D.
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15.

Stephany D.

I'll be your dog's other bestie!
madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking
5.0
26 reviews
10 repeat clients
from
$35
per night

Stephany was great. Dogs seemed so happy when we returned. So different from a stay at a kennel…. Much better! We will use this service again. Thankyou Stephany and Rover.

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Sitter Profile Image: Chun Hei C.
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Sitter Profile Image: Chun Hei C.
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16.

Chun Hei C.

Sharing my love with your pet
Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking
5.0
3 reviews
1 repeat client
from
$55
per night

Billy did an AMAZING job watching our Frenchies! He was very communicative throughout the stay and sent many photos and videos. He asked thoughtful questions about our pups and their behaviors and spent lots of quality time with them! We came home to a spotless house and happy pups - we look forward to having him stay with our dogs again! Thank you so much!

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Sitter Profile Image: Sarah T.
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Sitter Profile Image: Sarah T.
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17.

Sarah T.

Trustworthy, available pet lover!
Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking
5.0
6 reviews
3 repeat clients
from
$28
per night

Sarah was very calm and understanding when meeting our anxious and nervous dog Halla for the first time. Halla took treats from her and let her pet him, which usually doesn’t happen when he meets a new person. During our walk outside Halla was a bit of a jerk but she handled him very nicely. Hopefully Halla behaves better next time and matches Sarah’s calmness and kindness.

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Sitter Profile Image: Mckenzie T.
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Sitter Profile Image: Mckenzie T.
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18.

Mckenzie T.

Safe, communicative, & precise! 🐾
Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking
5.0
19 reviews
7 repeat clients
from
$45
per night

Mckenzie did an excellent job with our dogs! She sent us many updates so we knew they were being very well taken care of. Would definitely recommend booking her!!

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Sitter Profile Image: Emma C.
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Sitter Profile Image: Emma C.
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19.

Emma C.

wet kisses cold noses wagging tails
Parkwood Village, Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking
5.0
6 reviews
1 repeat client
from
$35
per night

We are so happy with the care Emma gave our dog. Our flight was cancelled and we had to stay another night. She checked in before we even asked! She dropped everything to spend another night with our pup and when we got home at last, Scout was happy and relaxed, like she just had a week at the doggy spa. Thank you Emma!

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Sitter Profile Image: Ciara T.
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Sitter Profile Image: Ciara T.
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20.

Ciara T.

All furbabies are loved!
Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking
10 years of experience
from
$28
per night

About: I have been taking care of all sorts of animals since I was a kid. Everything from goats to Great Danes! Making sure every animal is healthy and loved is paramount, and I’m here to help. I am currently working from home with a very flexible schedule so whatever time works for your pet, will more than likely work for me! I have an active, loving, easy going 4 year old dog at home. She loves going for walks, playing with her toys, and of course getting treats!

Search Map

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:

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