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. Whitney

I'll treat your furbaby like my own

Verona, WI, 53593

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Whitney was great! She came in for a drop-in visit while we were away for a day trip. Silly Millie got into things she wasn't supposed to and Whitney gladly ... (more)"

2. Christina

Anything fluffy, fuzzy, & floppy!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

3 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)"

3. Kelsey

Animal loving college student

Capitol, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I have owned animals all of my life especially dogs. Being in college I do not have the opportunity to own pets. I love going for walks and do that... (more)

Available this weekend
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. Christine

compassionate, experienced care

Prairie Hills, madison, WI, 54235

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

26 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)"

6. Anna

Dog lover with years of experience!

Capitol, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: Hello everyone! My name is Anna, and I have been a pet sitter and dog walker for over 10 years! Dogs are my greatest passion, and I love nothing mo... (more)

7. Erika

Experienced Pack Leader/Trainer

Leopold, Madison, WI, 53713

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

5 repeat clients

About: I would love to watch your dog! I have gained experience for all breeds and types as a pack leader and trainer at a local dog daycare. I have handl... (more)

8. Ben

I've got a passion for animals

Vilas, Madison, WI, 53711

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

1 repeat client

"Ben was patient with Winnie while she warmed up to him. The Rover app wasn't working properly so I only saw a couple of updates. Ben left a detailed message ... (more)"

9. Skylar

Dog loving academic!

Regent, Madison, WI, 53726

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Skylar did a great job with Dozer and was so good about posting updates so that I knew he was safe and happy while I was out of town. Couldn't have asked for... (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. Stephanie

Attentive animal lover just for you

Madison, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

5 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)"

12. 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)

13. 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)"

14. 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)"

15. 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)"

16. Crystal

Animal Lover

Madison, WI, 53719

Drop-In Visits, Dog Walking

8 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)"

17. Jillian

I would love to play with your dog!

Fitchburg, WI, 53719

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

"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)"

18. Amy

Energetic and passionate dog lover

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Amy is a caring and attentive sitter. She has watched my dog multiple times while I have had to travel for business. I received numerous updates on how my pu... (more)"

19. Kayla

Medical student dog lovers

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"2 Years ago Kayla rescued an aging Black and Tan Coon Hound, the love and care she gave this dog was beyond wonderful. Even when Ruby was diagnosed with term... (more)"

20. Amy

Reliable & Conscientious Caretaker

Hill Farms-University Neighborh, madison, WI, 53705

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

3 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)

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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: