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

7 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. 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)"

3. Christine

compassionate, experienced care

Prairie Hills, madison, WI, 53711

Dog Boarding, Drop-In Visits

32 repeat clients

"I have known Christine Nesheim through her work at our doggy daycare for two years. Christine also grooms both of my dogs and does so expertly. She is a to... (more)"

4. Daisy

I love dogs! Experience with dog sa

Capitol, Madison, WI, 53703

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

10 repeat clients

"Our dogs loved daisy! We have 3 large dogs and 1 small dog, we got pictures right away and everything went well, we would definitely use Daisy again (more)"

5. Erika

Experienced Pack Leader/Trainer

Leopold, Madison, WI, 53713

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

8 repeat clients

"Erika did an excellent job taking care of our dog while we were on vacation. She sent us daily updates, including photos of the dog, and even made sure our d... (more)"

6. 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)

Available this weekend
7. Gen

I'll love your dog like you do!

Westhaven Trails, Madison, WI, 53719

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

About: My dog and I would love to welcome yours to our home! We love walks and playtime and make time for both frequently. As a high-energy dog owner, I h... (more)

8. Whitney

Reliable & caring dog/cat sitter!

Madison, WI, 53719

Drop-In Visits, Dog Walking

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)

9. Stephanie

Attentive animal lover just for you

Madison, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Stephanie was wonderful! I was worried about leaving my cats and dogs for over a week, but Stephanie sent us an update every day. When we got home, everyone ... (more)"

10. 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)

Available this weekend
11. Jennifer

Loving Care When You're Not There!!

Madison, WI, 53719

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

"Max and Bailey, our chocolate labs, LOVE YOU!!! Thanks for taking such great care of us and taking us on long walks. We can't wait for you to stay the night ... (more)"

12. Adam

A friend of All Hunds

Orchard Ridge Community, Madison, WI, 53711

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

2 repeat clients

"Adam has provided great care for our dog. I would highly recommend him to other people! (more)"

13. Tony

I would love to meet your animals!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

"Tony was a great sitter for our dogs. He was incredibly reliable and caring and was willing to work around our schedules to help us take care of our pets. I ... (more)"

14. Jillian

I would love to play with your dog!

Fitchburg, WI, 53719

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

1 repeat client

"Jillian is so caring and good with animals! I 100% trust her with my dog. I never have to worry when i leave him with her, i know he is in great hands! (more)"

15. Shauna

Recommended and experienced sitter

Spring Harbor, Madison, WI, 53715

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Shauna took great care of my cat while I was away for the holidays. She communicated well throughout the booking process and stay, was able to administer hi... (more)"

16. Miranda

All dogs are good dogs!

Park Ridge, Madison, WI, 53719

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

1 repeat client

"Miranda is a very kind-hearted and compassionate person who loves pets almost as much as they love her. She always provides dogs with attention and affection... (more)"

17. Crystal

Animal Lover

Madison, WI, 53719

Drop-In Visits, Dog Walking

11 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)"

18. Danielle

I am dog's best friend!

Verona, WI, 53593

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

8 repeat clients

About: I am patient and kind, used to unruly puppies and dogs who need a little extra training. I will pay extra attention to whatever specific ways you a... (more)

19. Amy

Energetic, Responsible, Dog lover

madison, WI, 53705

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

"Amy is a loving caring dog owner and sitter. Amy has had a dog her entire life and is a true dog lover. Her pup gets walked 2-3 times per day, is taken to d... (more)"

20. Danae

fun and friendly and dog lover!

Wyndemere, Madison, WI, 53717

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

"As a long time friend of Danae's, I have seen, countless times, the love and affection she shows towards all animals. She is especially good with dogs, and s... (more)"

Experience exceptional service and a personalized match

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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: