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.

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1. Kaylin

Pick me for your Critter/Cat needs!

Oakbridge Community, Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"Kaylin was excellent! Dropped in on time and was very nice! I felt much better about leaving my cat at home knowing she would dropping in for feeding. (more)"

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2. Jenny

Walking for a living

Madison, WI, 53719

Drop-In Visits, Doggy Day Care, Dog Walking

"Jenny was AMAZING! I booked last-minute (less than 1 week) and she was able to squeeze in a meet-and-greet with Hodge Podge before their scheduled drop-in. S... (more)"

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3. Crystal

Animal Lover

Middleton, WI, 53562

Drop-In Visits, Dog Walking

"Crystal is great! She made me feel so at ease and is flexible and professional. I left my dog for the first time with a stranger and came home to a calm, qui... (more)"

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4. Krysta

Summer is for the dogs!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Krystal went above and beyond my expectations! Caring for my dog as if her own. She would carry my 150+ pound senior mastiff in and out when his hips were hu... (more)"

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5. Celia

Dogs big/cats small I love 'em all!

Madison, WI, 53705

Drop-In Visits, Dog Walking

"Celia was an unbelievable sitter for our two kitties. Great playful updates, and care in all she did. We can highly recommend Celia, and will be using her in... (more)"

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6. 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)"

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7. Ashley

Fun walks & fresh air for your dog!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

About: Hi there, I am Ashley! I have grown up with 5 dogs throughout my life and miss the constant energy! We have 2 cats currently that are quite active,... (more)

Confirmed availability
4th of July
8. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

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

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9. Mistie

Care + fun for your best friend

Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"Mistie V. is the epitome of a dog lover. She possesses a natural affinity for canines of all breeds and life cycle stages. Mistie is skilled at quickly devel... (more)"

10. Whitney

Reliable & caring dog/cat sitter!

Madison, WI, 53719

Drop-In Visits, Dog Walking

"Whitney was very conscientious when caring for Wrigley!!! (more)"

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11. Kristy

I'd love to walk your dog!

Madison, WI, 53705

Drop-In Visits, Dog Walking

"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)"

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12. Holly

Will treat your pup as my own

Madison, WI, 53719

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

"My dogs absolutely love Holly. Cooper, my 7 month old golden retriever puppy typically loves everyone but he gets especially excited when he sees her because... (more)"

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13. Jesse

25 yrs dogs/cats/horses/aggressive

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Jesse has house sat for us over the past few years. It’s not easy to get away when you have multiple animals, we have horses, dogs and cats do boarding them... (more)"

Confirmed availability
4th of July
14. Joseph

We love dogs! Fenced yard freedom!

Middleton, WI, 53562

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

"Joe's fun and laid back demeanor shows in his pets' (dogs) personalities. When they get too excited he doesn't get overly excited, but does have limits and ... (more)"

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15. Cleda

I love dogs and they love me!

Spring Harbor, Madison, WI, 53705

Dog Boarding, Drop-In Visits, Dog Walking

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)

Confirmed availability
4th of July
16. 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 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)"

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17. Sarah

Looking to meet some furry friends!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"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)"

18. Andrea

Huge animal lover

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

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

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19. Matthew & Rachael

Top-Notch Professional Pet Services

Madison, WI, 53719

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

"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)"

20. Mina

Experience with all kinds of pets~

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

About: (I will be available starting in May and be free all summer. Feel free to text or call me for details!) I have had life experience taking care o... (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:

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.