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. Danielle

I am dog's best friend!

Verona, WI, 53593

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

30 repeat clients

"I could not have imagined a better dog (puppy) sitter than Danielle! She is very knowledgeable about puppies/dogs! She is consistent, reliable and trustworth... (more)"

2. Crystal

Animal Lover

Middleton, WI, 53562

Drop-In Visits, Dog Walking

19 repeat clients

"Crystal was fantastic. I met with her before she watched my dog and immediately felt comfortable seeing how much she cared for her own and how good she was w... (more)"

3. Celia

Dogs big/cats small I love 'em all!

Madison, WI, 53705

Drop-In Visits, Dog Walking

5 repeat clients

"Celia was fantastic to work with! When something came up with her schedule and we needed to make adjustments, she let me know right away and I truly felt so ... (more)"

4. Andrea

Around the clock care, fenced yard!

Sunset Village, Madison, WI, 53705

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

64 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)"

5. Kiersten

Corgis are my spirit animal.

Regent, Madison, WI, 53726

Drop-In Visits, Dog Walking

6 repeat clients

"I would recommend Kiersten to everyone! She has come and seen our puppy several times. She is extremely reliable and flexible. We are so lucky to have found ... (more)"

Confirmed President's Day Availability
6. Cleda

I love dogs and they love me!

Spring Harbor, Madison, WI, 53705

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

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 President's Day Availability
7. Christine

Outdoorsy, Dog Park Lover, Vet Tech

Prairie Hills, Madison, WI, 53711

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

About: Hello! I have worked as a vet tech in for several years and have medical knowledge needed to care for special needs pets. I enjoy the outdoors an... (more)

8. Kristy

Home almost full-time, fenced yard

Oakbridge Community, Madison, WI, 53717

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

2 repeat clients

"Kristy would be the first person I would think of for doggie daycare for my pet! She is reliable, loving, fun, creative, and did I mention dependable? (I fin... (more)"

Confirmed President's Day Availability
9. Christina

Anything fluffy, fuzzy, & floppy!

Prairie Hills, Madison, WI, 53711

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

23 repeat clients

"Christina was wonderful! She did a great job, was very responsive...we recieved multiple pictures and updates daily. I would highly recommend her! She gave o... (more)"

10. Issie

I'm an affectionate caregiver

Spring Harbor, Madison, WI, 53705

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

About: Your dog can expect enthusiastic, engaged attention, care, pets and play. I’m comfortable with most dogs, of all ages and sizes, am also compassion... (more)

11. Rhea

Love to play and very dependable

Madison, WI, 53705

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

About: I will take care of your dog as if it was my own! I have over 10+ years of dog care experience, ranging from dogs of all breeds, sizes and care l... (more)

12. Joy

New best pal for your dog!

Middleton, WI, 53562

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

1 repeat client

"Joy is Amazing! I have seen her care for her own Sheltie as well as many other people's dogs on many occaisions and know that she will be great with your ... (more)"

Confirmed President's Day Availability
13. 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)"

14. 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)"

15. Dr. Elisa

Active dog-loving veterinarian!

Madison, WI, 53719

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

2 repeat clients

"Elisa goes above and beyond to make sure your furry friends are comfortable, safe, and having the time of their lives. She's experienced with dogs of all tem... (more)"

16. Michelle

At-home CPA who loves fur babies!

Hill Farms-University Neighborh, Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"If you want more bang for your buck, Michelle is outstanding! As a dogsitter, she's a natural - our golden, Abbie, took to her immediately. She also sent r... (more)"

Confirmed President's Day Availability
17. Glenis

Every Dog Has its Staycay

Spring Harbor, MADISON, WI, 53705

Dog Boarding, Drop-In Visits, Doggy Day Care

22 repeat clients

About: Missing our Bayley (Treeing Walker Coonhound), so need a pooch fix. We'll care for your dog(s) (max. of three/night) while you go away to play....... (more)

Confirmed President's Day Availability
18. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

6 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)"

Available this weekend
19. Jackson

No dog too big or too small

Spring Harbor, Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

About: I’m young, fit, and in the military. Ive been around dogs my whole life and am not easily intimidated. This is a dream job for me. I love dogs all ... (more)

20. Kelsey

Want a 4 day weekend get-away?

Madison, WI, 53705

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

2 repeat clients

"Kelsey is wonderful! She walks our golden doodle puppy on a regular basis and also has popped last minute to help us out in a pinch! She's on-time, trustwo... (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: