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Pet Sitting & 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.

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1. Kathryn & Joseph Verified Background Check

Full Time at Home with Fence + Love

Verona, WI, 53593

Dog Boarding, Drop-In Visits, Doggy Day Care

"Kathryn and Joseph were FANTASTIC with my sweet Gary! This was my first time using Rover and they made the experience better than I could have imagined. They w… (more)"

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2. Emily Verified Background Check

Lover of Animals & Exercise!

Vilas, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"Emily was amazing from start to finish on every walk she took my dog Ozzie on. When Emily first started taking care of Ozzie they almost warmed up to each othe… (more)"

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3. Bryan Verified Background Check

I am the definition of a dog person

Park Ridge, Madison, WI, 53719

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

"Dakota loved having Bryan drop in 2x a day while I was out of town. And I really appreciated the detailed report Bryan left after each visit. He let me know ex… (more)"

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4. Gen Verified Background CheckRover 101

The best care for your best friend!

Westhaven Trails, Madison, WI, 53719

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

"Amazing! Gen was so great, we were first time Rover users because we just needed someone to come let our pup out and give him dinner during our wedding, and sh… (more)"

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5. Brianna & Tyler Verified Background Check

For dogs that love attention

Allied Community, Madison, WI, 53711

Dog Boarding, Drop-In Visits, Doggy Day Care

"Brianna is the best... very responsible, conscientious, great communicator. She went "over and above" in caring for my cat Bennie. (more)"

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6. Nelly Verified Background Check

Best Dog Walker in Downtown Madison

Madison, WI, 53719

Drop-In Visits, Dog Walking

"Nelly has been a go to dog sitter for years. She’s so kind and my dog thinks so too! My pup always comes back in a great mood after spending time with Nelly. I… (more)"

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7. Ashley Verified Background Check

Treating Your Furbabies Like My Own

Oakbridge Community, Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"Ashley did a great job walking our dog and keeping our cat company. Love her updates after each visit! (more)"

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8. mary Verified Enhanced Background Check

I will care for your pets as my own

Midvale Heights Community, Madison, WI, 53711

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

"Mary has been great taking care of my two cats! Always prompt to get back to me and very flexible with my changing schedule. My cats get along great with her. … (more)"

9. Ashley Verified Background Check

Can't wait to get to know you!

Madison, WI, 53719

Dog Boarding, Drop-In Visits, Dog Walking

"Ashley went above and beyond with my dog who has a lot of anxiety. She knew immediate what to do with her professional experience! We are definitely going to b… (more)"

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10. Ryan & Jocelyn Verified Background Check

Dog Loving Small Family

Greentree, Madison, WI, 53711

Dog Boarding, Drop-In Visits, Doggy Day Care

"Ryan & Jocelyn are wonderful dog sitters and all around outstanding human beings: conscientious, caring, patient, and warm. They have watched my dogs - littl… (more)"

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11. Cleda Verified Background CheckRover 101

Dogs & Cats LOVE me!

Spring Harbor, Madison, WI, 53705

Dog Boarding, Drop-In Visits

"Cleda took good care of Bailey while we were gone. I could tell from the pictures she sent that Bailey loved having her visit. I would definitely book again. (more)"

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12. Charlene Verified Enhanced Background Check

Vet student w/ hands-on experience

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Thank you Charlene! Gertie said she had a great time hanging out and is so happy you stopped by. Charlene is extremely friendly and professional and we will de… (more)"

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13. Hannah Verified Background CheckRover 101

Dogs love to run and play with me!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

"Hannah took great care of our big sweetie Fergie and we can’t wait to have her back! (more)"

14. Tom Verified Background Check

Home full time.

Spring Harbor, Madison, WI, 53705

Drop-In Visits, Dog Walking

"We are so fortunate to have found Tom. He is a godsend. He has helped us so much with training our new puppy. (more)"

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15. Autumn Verified Background Check

Looking for some new furry friends!

Spring Harbor, Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Autumn was awesome with our cats! She sent quick responses and photos of how the two of them were doing when she checked in on them and fed them! Would definit… (more)"

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16. Kagen Verified Background CheckRover 101

Enthusiastic Dog Lover

Prairie Hills, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"Kagen has been great. She filled in for me on short notice and responds quickly, which is something I really appreciate. My dog was cared for and she provided … (more)"

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17. Laura Verified Background Check

Caring, kind and flexible

Sauk Creek, MADISON, WI, 53717

Drop-In Visits, Dog Walking

"Laura is a caring and compassionate dog owner, and has taught me so much about caring for and raising dogs of our own. Laura is deeply committed to the health… (more)"

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18. Hannah Verified Background Check

Large Breed Lover!

Madison, WI, 53719

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

"Hannah watched my crazy kitten for a week, housing him in her apartment. He was taken such good care of while I was gone and it was so nice to not have to stre… (more)"

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19. Stacy Verified Background Check

Looking for stress relief! :)

Madison, WI, 53705

Drop-In Visits, Dog Walking

About: Hi! I’m Stacy, a second year pharmacy student at UW Madison and animals help me relieve my stress! Help a girl out! I also love going to dog parks an… (more)

20. Johanna Verified Background Check

empathetic animal whisperer

Hill Farms-University Neighborh, Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Johanna has provided very thoughtful, TLC for our dogs (and cat) - multiple times. She's a natural w/ animals, so clearly enjoying them - and them, her. We fel… (more)"

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: