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.

Confirmed Easter Weekend Availability
1. Christina

Anything fluffy, fuzzy, & floppy!

Prairie Hills, Madison, WI, 53711

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

4 repeat clients

"Christina set my mind at ease during the meet and greet. She did drop in visits with my dog while I was away and each time she came over she let me know when... (more)"

2. Erika

Experienced Pack Leader/Trainer

Leopold, Madison, WI, 53713

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

7 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)"

3. 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)"

4. Stephanie

Attentive animal lover just for you

Madison, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"I have hired Stephanie two time now to take care of my cat while out of town. She does an excellent job! She is also great about communicating and always se... (more)"

Confirmed Easter Weekend Availability
5. Amanda

Reliable, Compasionate Dog Lover

Verona, WI, 53593

Drop-In Visits, Dog Walking

"Amanda is the biggest animal lover I have ever met! She has always been amazing with my two dogs and treats them like her own. My dogs love spending time wit... (more)"

6. Cindy

I will be your dogs best friend!

Hill Farms-University Neighborh, Madison, WI, 53705

Drop-In Visits, Dog Walking

"Cindy did a great job taking care of my boy when I had a long Saturday trip. She sent me lots pictures of him playing and then when he got stung by a bee off... (more)"

Confirmed Easter Weekend Availability
7. Courtney

Loving family home!

Fitchburg, WI, 53711

Dog Boarding, Drop-In Visits

About: We are experienced foster parents of rescue dogs and have a small dog of our own, Beans. We're sure Beans will be your pup's new best friend after ... (more)

8. 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)"

Confirmed Easter Weekend Availability
9. Claire

Responsible, loving, and patient.

Capitol, Madison , WI, 53703

House Sitting, Drop-In Visits, Dog Walking

About: Having worked in an animal shelter for 3 years, I have dog behavior and safety training that not many other people have an opportunity to acquire. ... (more)

10. 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)"

11. Morgan

Canine Rescuer, Trainer & Dog Lover

Greenbush, Madison, WI, 53715

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client
No Reviews Yet

About: Is your dog high energy or loves just cuddling up on the couch? Does your dog love running and playing with other dogs? If so, you've found the... (more)

12. Meghan

Dog Sitting and Walking

Vilas, Madison, WI, 53711

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

2 repeat clients

About: I grew up in a household that always had multiple dogs, both large and small so I'm comfortable around all shapes and sizes. But, now I'm in school... (more)

13. 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)

Confirmed Easter Weekend Availability
14. Matthew

Experienced with high energy dogs

Dudgeon-Monroe, Madison , WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"As a long-time runner and cyclist, Matthew has always enjoyed outdoor activities and dogs have been a integral part of his life; from the bike-path, to the t... (more)"

15. Miranda

All dogs are good dogs!

Park Ridge, Madison, WI, 53719

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

"Miranda is, in my opinion, one of the most responsible and caring pet caregivers I have know. The amount of love and care she provides for her own dog, Ch... (more)"

16. Devon

Lifelong dog lover

Blackhawk, Madison, WI, 53717

Drop-In Visits, Dog Walking

"Before I met Devon I didn't even like dogs. Her unconditional love for animals turned me into a dog lover, so much that I even own a dog myself now. There is... (more)"

17. 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)"

18. Susan

You'll never catch me without a dog

Vilas, Madison, WI, 53711

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

1 repeat client

"My mom is always caring, playful, and mindful with the pets she babysits for and she really makes an effort to build a friendship with the animals. I'm conti... (more)"

19. 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)"

20. Danielle

I am dog's best friend!

Verona, WI, 53593

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

3 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)

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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: