Pet Setting & Drop Ins in Oakwood Village, 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

23 repeat clients

"Danielle did a fabulous job!!! Our cats were very well taken care of. Danielle also went above and beyond when she came and stayed longer when there was seve... (more)"

2. Alexis

Experienced dog handler

Verona, WI, 53593

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Alexis did a great job with my puppy. I appreciated her flexibility and updates during her visits. (more)"

3. Gen

I'll love your dog like you do!

Westhaven Trails, Madison, WI, 53719

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

4 repeat clients

"Gen came over to play with the pooch for a while when I had to be gone for 12+ horurs, and Paco seemed happy and playful when I returned. No problems at all... (more)"

4. Amy

Self employed and flexible

Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Amy was an excellent caregiver to our dog Emma and our independent cat Lati. She has a wonderful way with animals, and they seem to connect with her without... (more)"

5. Kiersten

Corgis are my spirit animal.

Regent, Madison, WI, 53726

Drop-In Visits, Dog Walking

5 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)"

6. Luke

Mobile, exercise and care oriented.

Capitol, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Luke was great! My dog loved his energy and got along with him well. Communication was excellent both before and during the visit, and he was very flexible i... (more)"

7. Christine

A tired dog is a good dog

Prairie Hills, madison, WI, 53711

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

37 repeat clients

"Christine on many occasions has house sit and watched our dogs, we always knew that they were in goods hands. Christine has a love of dogs and it shows. If... (more)"

8. Christina

Anything fluffy, fuzzy, & floppy!

Prairie Hills, Madison, WI, 53711

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

11 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)"

9. Sonoma

Active and lots of free time!

South Campus, Madison, WI, 53715

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

"Sonoma went above and beyond. Highly recommended!!! (more)"

10. Joy

New best pal for your dog!

Middleton, WI, 53562

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

1 repeat client

About: Hello! My name is Joy and I am a fun, outgoing, dog-loving, and active Madison professional! I have a 5-year old Sheltie named Luna, who is sweet a... (more)

Available this weekend
11. Lauren

Lauren on the West Side

Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

About: Affection, attention, and tender loving care. You can be assured your pet will receive all of these when I'm the sitter. Animals bring me a lot of ... (more)

12. Jennifer

AVAILABLE THIS WEEKEND!!!

Madison, WI, 53719

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

5 repeat clients

"Jennifer was very prompt on responses and great with our dog (who can be a handful). She kept him entertained and even worked on training with him. We knew ... (more)"

13. Heather

a person who says hi to dogs first

Wisconsin Co-Op Housing, Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Heather is a fantastic dog caregiver! As the owner of two very different (and slightly odd) dogs, I can 100% vouch for Heather's ability to gain a dog's trus... (more)"

Available this weekend
14. Glenis

Every Dog Has its Staycay

Spring Harbor, MADISON, WI, 53705

Dog Boarding, Drop-In Visits, Doggy Day Care

17 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)

Available this weekend
15. Whitney

Reliable & caring dog/cat sitter!

Madison, WI, 53719

Drop-In Visits, Dog Walking

2 repeat clients

"Whitney did a great job with our 3 pups while we were on vacation. I could rest easy knowing they were being taken care of and it was nice to get the report ... (more)"

16. Matthew

Animal Lover

Madison , WI, 53719

House Sitting, Drop-In Visits, Dog Walking

About: I love dogs, they are like family to me. I have a dog of my own and I give him the love he desires. I've had 3 dogs in my past, two of them were La... (more)

17. Amy

Energetic, Responsible, Dog lover

madison, WI, 53705

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

1 repeat client

About: I grew up with dogs and I have a very sweet and high energy 1 1/2 year old goldendoodle. I am very energetic and patient and love dogs of all sizes... (more)

18. Amy

Love and Patience!

Regent, Madison, WI, 53726

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

3 repeat clients

"Amy's flexibility and willingness to roll with unexpected changes is incredible and amazingly helpful. We suddenly had to deal with an emergency with one of ... (more)"

19. Rebecca

Fun times for your dog!

Junction Ridge, middleton, WI, 53562

Dog Boarding, Drop-In Visits, Dog Walking

"I have always trusted Becca to take care of my dogs when I was away. She has always done a great job and my dog Bongo have always come back happy and healthy. (more)"

20. Hannah

I'm probably as active as your dog!

Junction Ridge, Madison, WI, 53717

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

4 repeat clients

"Really friendly and did a really great job taking care of my dog. (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 423 owners have reviewed sitters in Oakwood Village, Madison, WI, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Oakwood Village, Madison pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in Oakwood Village, Madison who can provide the care your pet needs, when they need it.

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 Oakwood Village, 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: