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.

Available this weekend
1. Christina

Anything fluffy, fuzzy, & floppy!

Prairie Hills, Madison, WI, 53711

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

8 repeat clients

"Christina was terrific! With each visit she gave us an update along with pics of the dogs playing, eating and relaxing. We'll certainly be working with her... (more)"

2. Whitney

Reliable & caring dog/cat sitter!

Madison, WI, 53719

Drop-In Visits, Dog Walking

2 repeat clients

About: Hi! My name is Whitney and I have pet-sit for both dogs and cats, and walked dogs in the past. I love spending time with and caring for animals of ... (more)

3. Luke

Mobile, exercise and care oriented.

Capitol, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

"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)"

4. Amy

Love and Patience!

Regent, Madison, WI, 53726

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

3 repeat clients

"Amy is great with my two (kind of high maintenance) beagles. She "dropped in" with one of them and walked the other while I was at work, and both of them wer... (more)"

5. Joy

Active, reliable, and fun dog lover

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"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)"

6. Amy

Self employed and flexible

Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

About: I have had dogs and animals all my life. I started a dog walking service in San Francisco when it was a rare service. I love being active and outdo... (more)

7. Kiersten

Corgis are my spirit animal.

Regent, Madison, WI, 53726

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

5 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)"

Available this weekend
8. Gen

I'll love your dog like you do!

Westhaven Trails, Madison, WI, 53719

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

2 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)"

9. Danielle

I am dog's best friend!

Verona, WI, 53593

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

10 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)"

10. 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)

11. Alecia

Loving dog walker!

Fitchburg, WI, 53713

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

"Loved Alecia as my dog walker for my Husky, Sam. She provided great care and love for my dog while I was at work. She always made sure his food and water bow... (more)"

Available this weekend
12. Miranda

Energetic dog? Home full time!

Madison, WI, 53018

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

"Miranda did a great job doing drop in visits with our three dogs! She bonded with them right away at the meet and greet and got all their individual quirks r... (more)"

13. Erika

Experienced Pack Leader/Trainer

Leopold, Madison, WI, 53713

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

8 repeat clients

"Great experience! (more)"

14. Michelle

Reliable Dog Lover

Oakbridge Community, Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

1 repeat client
No Reviews Yet

About: I've always been a huge dog lover, tried to take in every stray as a kid, I grew up around dogs like basset hounds, Labradors, poodles and beagles.... (more)

15. Brenna

Graduate student animal lover!

Vilas, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"Being an animal lover is core to who Brenna is. Her loving and gentle nature allows her to quickly bond with every dog, cat, or other furry friend she meets.... (more)"

16. 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)"

17. Ashley

Will run/be active with your dog!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

"She loves animals and enjoys long runs and walks. She a honest trustworthy person and will take great care of someone's pet. She's graduated from Uw Milwauke... (more)"

18. Miranda

Around the clock care & cuddles!

Park Ridge, Madison, WI, 53719

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

6 repeat clients

"Miranda is super awesome with animals in general, if I ever need someone to walk my dog or babysit I would definitely give her a call (more)"

Available this weekend
19. Jennifer

AVAILABLE THIS WEEKEND!!!

Madison, WI, 53719

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

2 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)"

20. Crystal

Animal Lover

Madison, WI, 53719

Drop-In Visits, Dog Walking

13 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)"

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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: