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

20 repeat clients

"Simply put, Crystal is phenomenal. She has helped with our dog for several months and we have been impressed with her kindness, reliability, attention to det... (more)"

2. Danielle

I am dog's best friend!

Verona, WI, 53593

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

32 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)"

3. Whitney

Reliable & caring dog/cat sitter!

Madison, WI, 53719

Drop-In Visits, Dog Walking

5 repeat clients

"Super mega awesome. Whitney provided us with a ton of peace of mind that our cats would be well taken care of while we were gone. (more)"

4. 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)"

5. Andrea

Around the clock care, fenced yard!

Sunset Village, Madison, WI, 53705

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

69 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)"

6. 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)"

7. Christina

Anything fluffy, fuzzy, & floppy!

Prairie Hills, Madison, WI, 53711

Dog Boarding, House Sitting, 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)"

8. Sarah

Great with all animals!

Madison, WI, 53719

Drop-In Visits, Dog Walking

"Sarah is a very caring person and really loves animals. She's taken care of a horse as well for many years, and has done a great job. She will take great car... (more)"

9. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

9 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)"

10. Brenna

Graduate student animal lover!

Vilas, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

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

11. Amy

Reliable & Conscientious Caretaker

Hill Farms-University Neighborh, madison, WI, 53705

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

9 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)"

12. Cara

Apt life has me missing dog life!

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

About: You will love my love for your furry babies! I grew up with various breeds (labs, king Charles spaniels, beagles) and love dogs of all sizes. I hav... (more)

13. Christine

Outdoorsy, Loving Vet Tech

Prairie Hills, Madison, WI, 53711

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

1 repeat client

About: Hi! I am a Certified Veterinary Technician and have worked with pets professionally my whole life! I have personally owned a horse, fish, lizards... (more)

14. Cleda

I love dogs and they love me!

Spring Harbor, Madison, WI, 53705

Dog Boarding, Drop-In Visits, Dog Walking

3 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)

15. Rebecca

Fun times for your dog!

Junction Ridge, middleton, WI, 53562

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Rebecca is a caring dog owner and is very knowledgeable and attentive to her dogs' needs. She knows how to have fun with them and to comfort them when they'r... (more)"

16. Celia

Dogs big/cats small I love 'em all!

Madison, WI, 53705

Drop-In Visits, Dog Walking

8 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)"

17. Gen

I'll love your dogs like you do!

Westhaven Trails, Madison, WI, 53719

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

11 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)"

18. 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 is a true dog lover. She is so close with her own dog, and she lights up when she is around other dogs. She is a very active person who can keep a dog... (more)"

19. Jennifer

AVAILABLE THIS WEEKEND!!!

Madison, WI, 53719

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

8 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)"

20. 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

"Michelle was GREAT !!! She took good care of my 2 dogs while I was gone, sent lots of pics and keep me very informed. (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: