House Sitting in Woodlands, 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.
1. Alexis

Experienced dog handler

Verona, WI, 53593

House Sitting, Drop-In Visits, Dog Walking

"I was nervous about leaving my dog for a week. When we first met Alexis, he immediately warmed up to her and even brought her a you to play with. This never ... (more)"

2. Allison & Raymon

LOVING, ACTIVE DOG SITTERS!!

Capitol, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

"I needed to try out a new house/dog sitter on relatively short notice so that I could travel over a weekend (Fri - Sun). Allison was great at setting a meet ... (more)"

Confirmed 4th of July Availability
3. Kaylin

Pick me for your Critter/Cat needs!

Oakbridge Community, Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"We've been using Kaylin as a pet sitter for our senior cat (Halle Berry) for a few years now and could not be happier! Kaylin is friendly, dependable, and al... (more)"

4. Amy

Reliable & Conscientious Caretaker

Hill Farms-University Neighborh, madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Amy did a great job taking care of our fur baby. I would highly recommend Amy, she sent me updates and we had a very happy puppy when we returned home. (more)"

5. Brenna

Graduate student animal lover!

Vilas, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"Brenna did a fantastic job. My dog can be labor-intensive, but I felt like Brenna had everything under control. And she kept in contact with me, which I ap... (more)"

6. Kaylyn

Full-time care, Lots of Walks!

Middleton, WI, 53562

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

"I would highly recommend Kaylyn. She stayed at our house with our senior dog Lulu, and took great care of her. Our dog has some special needs after back surg... (more)"

7. Mistie

Care + fun for your best friend

Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"Mistie was so helpful leading up to the trip I took! She was very accommodating in transferring keys over to her, and I felt comfortable knowing that she was... (more)"

8. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

"Fran did a fantastic job watching my dog Java. She sent me pictures of Java and little notes about how she was doing. Fran responded quickly to my messages. ... (more)"

9. Holly

Will treat your pup as my own

Madison, WI, 53719

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

"Holly did a wonderful job taking care of Daisy for me while I was gone for the weekend! I really appreciated being able to keep Daisy in our home and having ... (more)"

10. Jesse

25 yrs dogs/cats/horses/aggressive

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Jesse was a lifesaver when we were in a very difficult situation. Our dog had two seizures during the month of May and we needed to be out of town for 36hrs... (more)"

11. Jennifer

AVAILABLE THIS WEEKEND!!!

Madison, WI, 53719

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

"Jennifer was amazing! Sent a lot of updates (I am a worrying dog mom!!), and the boys were well cared for! Badger had a wound we were dealing with, and he lo... (more)"

12. Krysta

Summer is for the dogs!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Krysta took great care of our pup! It's so nice to know she was in good hands while we were gone. Thank you! (more)"

13. Megan

Adaptive to your dog's needs!

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Top notch dog sitter! Megan had become my go-to choice when u have to travel on weekends and my little hounds need care. She sends me pictures and updates ev... (more)"

14. Toni

4th year vet student

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"I was concerned first about leaving my older dog who was struggling with symptoms from a recent brain tumor diagnosis, and then my other tore his CCL just da... (more)"

15. Andrea

Huge animal lover

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Andrea did a great job caring for our dog, cats, chickens and house for 9 nights. She handled issues that came up in a responsible and appropriate way, and ... (more)"

16. Matthew & Rachael

Top-Notch Professional Pet Services

Madison, WI, 53719

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

"Matthew was great! Obviously good with dogs with high energy and even took notes during the meet and greet. Kept me updated while I was away and a really nic... (more)"

17. Amber

TLC always

Wisconsin Co-Op Housing, MADISON, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Whenever my family considers a go-away vacation, the first thing we do is check to see if Amber is available to look after our very energetic scotch collie, ... (more)"

Confirmed 4th of July Availability
18. Andrea

Around the clock care, fenced yard!

Sunset Village, Madison, WI, 53705

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

"Andrea was great- she took care of my chihuahua Coco last minute when on a work trip to Madison. She came to pick her up early from my hotel and dropped her ... (more)"

19. Hannah

I'm probably as active as your dog!

Junction Ridge, Madison, WI, 53717

Dog Boarding, House Sitting

"Hannah was wonderful. We arrived back home from our trip to find our dog happy and healthy and our home in great condition. Hannah was very attentive to our ... (more)"

20. Mina

Experience with all kinds of pets~

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Mina was wonderful and patient with my pup Abril. She is super nice and my puppy just loves her. I highly recommended Mina. Thanks again for taking good care... (more)"

Dog owners in Woodlands, Madison, WI love booking house sitting with sitters on Rover.com. Over 423 pet owners have reviewed house sitters in Madison, giving them an average rating of 4.9/5 stars. Booking house sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book house sitting with Rover? Check out our average house sitting rates to get an idea before reaching out and starting a conversation with a house sitter near you in Woodlands.

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 Woodlands, Madison house sitting needs. On Rover, it's easy to find a loving dog sitter in Woodlands, 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 Woodlands 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 Woodlands, 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 Woodlands, 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: