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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Christine

compassionate, experienced care

Prairie Hills, madison, WI, 54235

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

25 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)"

Confirmed Holiday Availability
2. 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)

3. 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)"

4. 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)"

5. Amy

Love and Patience!

Regent, Madison, WI, 53726

Drop-In Visits, Doggy Day Care, Dog Walking

3 repeat clients

"Amy's flexibility and willingness to roll with unexpected changes is incredible and amazingly helpful. We suddenly had to deal with an emergency with one of ... (more)"

6. 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)"

Confirmed New Years Availability
7. Emma

Furry or scaly, I love them all!

Appalachian Ridge, Madison , WI, 53705

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I'm a Horticulturist who is looking for winter work while the ground is frozen. I adore pets of all kinds, grew up with Belgian Tervuren and now ow... (more)

8. Stephanie

Attentive animal lover just for you

Madison, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

5 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)"

9. Alex

Active, energetic, & loving sitter!

Madison, WI, 53715

Drop-In Visits, Dog Walking

3 repeat clients

"Alex is so great with my pup, Rizzo! I love getting pics of whatever adventure they're on during her visit :) (more)"

10. 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)"

11. Sheryl

Let us spoil your dog!

Sunset Village, Madison, WI, 53705

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

About: My aunt was a dog breeder and I grew up around dogs from their inception. I helped with the breeding process, whelping, weaning, training for the r... (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. 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)

Confirmed New Years Availability
14. Christina

Anything fluffy, fuzzy, & floppy!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

15. Amy

Energetic and passionate dog lover

Madison, WI, 53705

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)"

16. Kayla

Medical student dog lovers

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

Confirmed Holiday Availability
17. 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 Holiday Availability
18. Kimberly

Unconditional love for "fur"-babies

Middleton, WI, 53562

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

2 repeat clients

About: My name is Kim! I'm 21 years old and currently work at a pet boarding facility. I've lived with dogs, cats, and one mini pig my entire life (I curr... (more)

19. 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)

Confirmed Holiday Availability
20. Lindsay

Owned by 3 experienced w/ many more

Madison, WI, 53719

Drop-In Visits, Dog Walking

About: I have owned dogs all my life and have experience with dogs ranging from 10-110 pounds, and all ages, temperaments and activity levels. I am famili... (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: