Pet Setting & Drop Ins in Woodland Hills, Madison, WI

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

1. Crystal

Animal Lover

Middleton, WI, 53562

Drop-In Visits, Dog Walking

25 repeat clients

"I couldn't have asked for a better drop-in than Crystal! This was my first time using Rover and my first time leaving my sweet old dog with a stranger rather... (more)"

2. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

12 repeat clients

"Thank you so much! We love having Bruno spend time with you so we can relax and not worry about him. Thank you! (more)"

3. Celia

Dogs big/cats small I love 'em all!

Madison, WI, 53705

Drop-In Visits, Dog Walking

10 repeat clients

"Celia recently cared for our two cats while we were out of town. She visited each day and gave the cats canned food, head rubs and a little play time, she ev... (more)"

4. Amy

Reliable & Conscientious Caretaker

Hill Farms-University Neighborh, madison, WI, 53705

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

10 repeat clients

"Amy did a wonderful job! She was flexible last minute to watch/walk our lab on Thanksgiving. Our pup was nice & tired after his long walks. Would recommend ... (more)"

5. Brenna

Graduate student animal lover!

Vilas, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"I really appreciated the help, photo and status that Brenna provided. She was comfortable with my high energy dog. (more)"

6. Krysta

Summer is for the dogs!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I couldn't think of anyone better to watch my pet. Krysta has been around animals her whole life to include her own two dogs growing up, helping her family a... (more)"

Confirmed Memorial day Availability
7. Kristy

I'd love to walk your dog!

Madison, WI, 53705

Drop-In Visits, Dog Walking

4 repeat clients

"Kristy would be the first person I would ask to watch our dog (if we still had a dog) because Kristy loves dogs and finds amazing things about every single o... (more)"

8. Sarah

Looking to meet some furry friends!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah has watched my dog for me several times while I was away on vacation for a few days. She has always taken good care for him, taking him for a walk at l... (more)"

9. Jesse

25 yrs dogs/cats/horses/aggressive

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Jesse has been dog,horse,kitty and house sitting for us on numerous occasions from short to extended trips abroad. I own a small hobby farm on which I entrus... (more)"

10. Cleda

I love dogs and they love me!

Spring Harbor, Madison, WI, 53705

Dog Boarding, Drop-In Visits, Dog Walking

5 repeat clients

About: I have a small dog myself and she is a diva. If I can handle her, I can handle any dog. We frequent the dog park and I've interacted with many dogs... (more)

11. Andrea

Around the clock care, fenced yard!

Sunset Village, Madison, WI, 53705

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

76 repeat clients

"Andrea really stepped in and helped me with Otis when I had to have surgery. She is always so good with Otis and he absolutely loves her. (more)"

12. Cara

Apt life has me missing dog life!

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Cara was great! I knew from our initial meeting it was going to work. She was thorough with her questions and took notes. The was my first time using Rover v... (more)"

13. Maiya

I'll love them like you love them!

Blackhawk, Madison, WI, 53717

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

About: I have loved animals since I was a little girl whether it be big or small, a pet fish or a pet horse, I am a true animal lover at heart, although ... (more)

14. Whittney

Love dogs with a passion!

High Point Estates, Madison, WI, 53719

Drop-In Visits, Dog Walking

1 repeat client

"I've had Whittney watch my two small dogs. One has a heart mumor and needs a little extra love. She made sure she understood how to give my Chihuahua her med... (more)"

15. Christina

Anything fluffy, fuzzy, & floppy!

Prairie Hills, Madison, WI, 53711

Drop-In Visits, Dog Walking

25 repeat clients

"Christina was absolutely amazing. We could not have asked for a better sitter for our girl or a for better first time rover experience. We highly recommend h... (more)"

Confirmed Memorial day Availability
16. 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)"

Confirmed Memorial day Availability
17. Jennifer

AVAILABLE THIS WEEKEND!!!

Madison, WI, 53719

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

10 repeat clients

"Jennifer was an amazing asset that was so great with my cat. I would never of been able to go on my vacation without her help. Even tough she was only sche... (more)"

18. Matthew & Rachael

Top-Notch Professional Pet Services

Madison, WI, 53719

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

4 repeat clients

"Matt is a passionate dog lover! I would trust him with my dog which is saying a lot becuase my dog loves to run away and actively pursues the challenge of g... (more)"

19. Andrea

Huge animal lover

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Andrea takes such good care of our Wrigley!! She is very detailed and a fantastic communicator!! (more)"

20. Rebecca

Fun times for your dog!

Junction Ridge, middleton, WI, 53562

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Rebecca is an amazing dog sitter and walker. She's taken care of Mocha my shih tzu on various occasions, and each time I felt completely comfortable leaving ... (more)"

Dog owners in Woodland Hills, Madison, WI turn to pet sitters on Rover.com for their pet sitting needs. Over 423 pet owners have reviewed pet sitters in Madison, giving them an average rating of 4.9/5. Pet sitting can be affordable, no matter where you live or what your price range may be. Curious about how much pet sitting costs in Madison with Rover.com? Check out our average pet sitting rates near you to get an idea before getting a conversation started with a pet sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Woodland Hills pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Woodland Hills, Madison, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). 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 house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Woodland Hills pet sitters and avoid the kennel.

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: