House Sitting in Woodland Hills, 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
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Calendar Recently Updated
Sitter Profile Image: Natalie B.
Verified Background Check
Sitter Profile Image: Natalie B.
Verified Background Check
1.

Natalie B.

Vet-Trained Animal Caretaker!
Madison, WI, 53703
House Sitting, Drop-In Visits, Dog Walking
5.0
31 reviews
13 repeat clients
from
$35
per night

Natalie was awesome! She communicated with us very well and sent us plenty of pictures of our pups. Thank you for taking care of our pups, our home and making us feel at ease. Highly recommended!

Calendar Recently Updated
Sitter Profile Image: Emma C.
Verified Enhanced Background Check
Sitter Profile Image: Emma C.
Verified Enhanced Background Check
2.

Emma C.

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

Emma has stayed overnight at our house with our dog and two kitties a few times. She is sweet, kind and has a quiet, gentle nature. She takes such great care of our Jelly Bean, Dinky and Russell. We feel very comfortable leaving them in Emma's very capable hands for any length of time. We met Emma through a kennel we used to use. Our pittie mix, Jelly Bean can be very shy, but she always went right to Emma with a very happy wiggle and plenty of kisses. We talked to her once or twice and she was able to take our girl home for us a couple of times, so she didn't have to wait an extra night for us to home (based on kennel hours). We highly recommend Emma to care for your animals, too.

Calendar Recently Updated
Sitter Profile Image: Jenny P.
Verified Enhanced Background Check
Sitter Profile Image: Jenny P.
Verified Enhanced Background Check
3.

Jenny P.

Rover 101
Professional furbaby snuggler
Fitchburg, WI, 53719
House Sitting, Drop-In Visits, Dog Walking
5.0
46 reviews
15 repeat clients
from
$120
per night

Jenny was wonderful! She did so many walks and sent us pictures, updates and videos. She took great care of the house and have our little bean so much love.

Sitter Profile Image: Chun Hei C.
Verified Enhanced Background Check
Sitter Profile Image: Chun Hei C.
Verified Enhanced Background Check
4.

Chun Hei C.

Sharing my love with your pet
Madison, WI, 53706
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!

Calendar Recently Updated
Sitter Profile Image: Azaria O.
Verified Enhanced Background Check
Sitter Profile Image: Azaria O.
Verified Enhanced Background Check
5.

Azaria O.

Pets don’t need us, we need them🙂
Verona, WI, 53593
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
17 reviews
5 repeat clients
from
$38
per night

Azaria was absolutely wonderful at taking care of my anxious pooch! She’s punctual and really personable. She even stayed longer than asked- which I really appreciate! Will definitely work with her again. Thank you Azaria

Calendar Recently Updated
Sitter Profile Image: Andrew L.
Verified Background Check
Sitter Profile Image: Andrew L.
Verified Background Check
6.

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
100 reviews
42 repeat clients
from
$89
per night

Andrew watched our dogs at our house for a week, and our babies LOVED the time with him. Lots of snuggles and attention, and Andrew kept us updated with lots of pictures. We have an older dog who needed some extra TLC, and Andrew was fantastic with his medical needs. House was in great shape when we got back, and we couldn't have asked for a better experience. Highly recommend this pet sitter.

Calendar Recently Updated
Sitter Profile Image: Elissa S.
Verified Enhanced Background Check
Sitter Profile Image: Elissa S.
Verified Enhanced Background Check
7.

Elissa S.

Lover of all animals!
Madison, WI, 53719
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4.5
11 reviews
2 repeat clients
from
$60
per night

Elissa is one of the best I’ve ever used. She is caring, compassionate, and most of all she is totally intentional about making the experience with my pup one of the best.

Calendar Recently Updated
Sitter Profile Image: Kelsee C.
Verified Enhanced Background Check
Sitter Profile Image: Kelsee C.
Verified Enhanced Background Check
8.

Kelsee C.

No dog too big or small 🐶
Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$30
per night

Kelsee is the biggest dog-lover I know. She treats her own dog, Winston, like a prince and is constantly thinking about him. She even has an entire wall of her home dedicated to “Winnie”! As a caretaker, she is very attentive and loving to every dog’s needs but still has the discipline not to let the dog “run the house”. It’s a line that very few people know how to tow and she does it seemingly effortlessly. Great choice for your canine needs!

Calendar Recently Updated
Sitter Profile Image: Rebecca D.
Verified Enhanced Background Check
Sitter Profile Image: Rebecca D.
Verified Enhanced Background Check
9.

Rebecca D.

A Cuddle-loving Dog Person!
Madison, WI, 53726
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$50
per night

Becky is so amazing and full of love for animals. She made my senior pup feel so comfortable and safe. We would definitely use her for our pups future needs ❤️

Calendar Recently Updated
Sitter Profile Image: Louisa M.
Verified Enhanced Background Check
Sitter Profile Image: Louisa M.
Verified Enhanced Background Check
10.

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
27 reviews
11 repeat clients
from
$55
per night

Louis and her family took good care of my dog. He seemed very happy the entire time and enjoyed their company. She made sure to send lots of pictures and check in too.

Sitter Profile Image: Sara J.
Verified Enhanced Background Check
Sitter Profile Image: Sara J.
Verified Enhanced Background Check
11.

Sara J.

I’ll take care of your PAWfect pup
Junction Ridge, Madison, WI, 53717
House Sitting, Drop-In Visits, Dog Walking
5.0
11 reviews
3 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.

Sitter Profile Image: Robert C.
Verified Background Check
Sitter Profile Image: Robert C.
Verified Background Check
12.

Robert C.

Home is where the bark is
Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking
5.0
95 reviews
40 repeat clients
from
$28
per night

I am perfectly satisfied with Robert's excellent care for my two dogs and my home for ten days and nights. He sent daily pictures and notes that were delightful and reassuring. I could see that my dogs were happy and well. I returned to my home exactly as I left it. I will choose Robert again in the future to dog and house sit. I hope he'll be willing and available! Thanks Robert!

Calendar Recently Updated
Sitter Profile Image: Jamaal A.
Verified Enhanced Background Check
Sitter Profile Image: Jamaal A.
Verified Enhanced Background Check
13.

Jamaal A.

A dog's best friend
Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking
10 years of experience
from
$28
per night

About: I've taken care of dogs from all ages and breeds. Easily assimilate and build trust with new interactions. And don't shy away from challenge. Love getting dogs to be active outdoors by going for walks, runs or just a leisurely stroll at the dog park. I am available early morning from 5 to 7am and after 5 pm Monday to Friday and available most weekends. Weekends, early riser so willing to wake up early and available most hours throughout the day with 9 pm being the latest. I provide house sitting at clients home which allows for pets to be comfortable in their natural surroundings. Depending on home layout, lesh will be used in open settings.

Sitter Profile Image: Kaylee C.
Verified Enhanced Background Check
Sitter Profile Image: Kaylee C.
Verified Enhanced Background Check
14.

Kaylee C.

Doggos&Cattos r better than people
University Apartments, Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking
5.0
8 reviews
3 repeat clients
from
$50
per night

Kaylee was fantastic! She was communicative, punctual, and went above and beyond expectations. I felt very comfortable leave my anxious dog in her care. I got many updates from her, with pictures! She was respectful and left the house in great shape. I highly recommend her.

Sitter Profile Image: Max C.
Verified Enhanced Background Check
Sitter Profile Image: Max C.
Verified Enhanced Background Check
15.

Max C.

Experienced Pet Sitter and Walker
Regent, Madison, WI, 53726
House Sitting, Drop-In Visits, Dog Walking
5.0
4 reviews
1 repeat client
from
$30
per night

Max was great. Good communication. Dogs did well with him. Highly recommend

Calendar Recently Updated
Sitter Profile Image: Ben P.
Verified Enhanced Background Check
Sitter Profile Image: Ben P.
Verified Enhanced Background Check
16.

Ben P.

It’s fun walking with a happy dog
Madison, WI, 53719
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
55 reviews
16 repeat clients
from
$44
per night

Ben was an excellent pet sitter for our week away from home!

Sitter Profile Image: Bree C.
Verified Background Check
Sitter Profile Image: Bree C.
Verified Background Check
17.

Bree C.

Not-So-Crazy Cat Lady
Madison, WI, 53711
House Sitting, Drop-In Visits
5.0
46 reviews
24 repeat clients
from
$60
per night

Bree took care of our five month old pup for five days! She is very professional and clearly experienced. She worked with us to outline a care plan for our pup that would meet his health and energy needs. This was our first time leaving our little guy for an extended period of time and I was very nervous about it. Bree did such a good job addressing my concerns and sending me updates. We won't hesitate to book her again the next time we are out of town!

Calendar Recently Updated
Sitter Profile Image: Kate K.
Verified Enhanced Background Check
Sitter Profile Image: Kate K.
Verified Enhanced Background Check
18.

Kate K.

Rover 101
Cared for as if you were home
Middleton, WI, 53562
House Sitting, Drop-In Visits
5.0
31 reviews
14 repeat clients
from
$55
per night

Kate was fabulous!!! She went above and beyond for all our pets including the fish. Everyone was healthy and happy when we came home and house was in good order. Would difinately book again!!!!!

Calendar Recently Updated
Sitter Profile Image: Alisyn L.
Verified Enhanced Background Check
Sitter Profile Image: Alisyn L.
Verified Enhanced Background Check
19.

Alisyn L.

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

Alisyn once again took excellent care of Myla (my dog), my fish, and my plants for an entire week while I relaxed on vacation. I am so happy to have found a trustworthy and kind person to watch over Myla and my home. I don’t worry about a thing and she sends me updates daily. I highly recommend Alisyn!

Sitter Profile Image: Kally G.
Verified Enhanced Background Check
Sitter Profile Image: Kally G.
Verified Enhanced Background Check
20.

Kally G.

Fun sitter with small service dog
Middleton, WI, 53562
House Sitting, Drop-In Visits, Dog Walking
5.0
51 reviews
15 repeat clients
from
$25
per night

Kally took wonderful care of our Ellie girl while we were away for the weekend. She and her service dog, Roxie, really made our pup feel cozy, comfortable and safe the whole time. Kally sent us many welcomed videos and pictures of their time together and was especially helpful throughout Ellie’s thunderstorm jitters! We definitely plan on rebooking with Kally and Roxie again in the future!

Search Map

Dog lovers in Woodland Hills, Madison, WI love house sitters on Rover.com. Over 423 pet owners have reviewed house sitters on Rover in Madison, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable house sitting in Madison can be when you book with Rover. Wondering how much it might cost to book house sitting? Check out our average house sitting rates to get an idea before contacting a house sitter near you.

Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog and your home, turn to Rover for your Woodland Hills, Madison house sitting needs. On Rover, it's easy to find a loving dog sitter in Woodland Hills, Madison, WI who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Woodland Hills house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover: it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Woodland Hills, Madison, WI for your dog: people who'll treat him like family.

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 Woodland Hills, 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:

House Sitting