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. Crystal

Animal Lover

Middleton, WI, 53562

Drop-In Visits, Dog Walking

17 repeat clients

"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)"

Confirmed Thanksgiving Availability
2. Alexis

Experienced dog handler

Verona, WI, 53593

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

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

3. Christina

Anything fluffy, fuzzy, & floppy!

Prairie Hills, Madison, WI, 53711

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

18 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)"

4. Maryrose

I'll walk any dog in any weather.

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"MaryRose is one of the most responsible people I know, and a fantastic dog caregiver. She is excellent at setting dogs of all ages, sizes, and breeds at ease... (more)"

5. Amy

Reliable & Conscientious Caretaker

Hill Farms-University Neighborh, madison, WI, 53705

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

7 repeat clients

About: I grew up taking care of my 20 pound dog and now regularly care for two 50 and 80 pound dogs. While they keep me busy, I still have time for dog si... (more)

Confirmed Thanksgiving Availability
6. Andrea

Around the clock care, fenced yard!

Sunset Village, Madison, WI, 53705

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

60 repeat clients

"Andrea watched our dog for over a week and she was so happy to have a great house to stay in and a spacious yard to roam around in, not to mention a loving h... (more)"

7. 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)"

8. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

3 repeat clients

"Fran is the absolute best. She came to stay at our house and look after our pup and she was the best houseguest and dogsitter ever. First of all, our dog Fox... (more)"

Confirmed Thanksgiving Availability
9. Jennifer

AVAILABLE THIS WEEKEND!!!

Madison, WI, 53719

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

6 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)"

10. Kiersten

Corgis are my spirit animal.

Regent, Madison, WI, 53726

Drop-In Visits, Dog Walking

6 repeat clients

"Kierstin was awesome...so sweet...and she made her available to help out with a urgent medical need at the last minute. I would definately use her again in ... (more)"

11. Amy

Love and Patience!

Regent, Madison, WI, 53726

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

4 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)"

Confirmed Thanksgiving Availability
12. Whitney

Reliable & caring dog/cat sitter!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

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

"Awesome sitter! Sent pictures and updates daily! (more)"

14. Dr. Elisa

Active dog-loving veterinarian!

Madison, WI, 53719

Dog Boarding, House Sitting, 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)"

15. Celia

Dogs big/cats small I love 'em all!

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Celia was great with my pup Logan! He absolutely loved her. She was also very friendly and easy to talk to. I will definitely have her doggy sit my pup again! (more)"

Confirmed Holiday Availability
16. Ashley

Energizing walks and fresh air!

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! Dog sitting sounds like a perfect fit for me to... (more)

17. Matthew

Top-Notch Professional Pet Services

Madison, WI, 53719

House Sitting, Drop-In Visits, 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)"

18. Michelle

At-home CPA who loves fur babies!

Hill Farms-University Neighborh, Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

3 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)"

19. Abigail

Pre-Vet Grad. 10 yrs of Animal Care

Meadowood, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"Abigail is our first call when we’re skipping town for a long trip. Why? Let’s start with dog sense - Abby understands our two very unique dogs. She doesn’t ... (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)"

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: