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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.

Tip: Contact sitters now to confirm availability.
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1. Kaylin

Pick me for your Critter/Cat needs!

Oakbridge Community, Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"Kaylin went above and beyond while caring for our cat Khaleesi! Her visits were prompt and her check-in descriptions were detailed and filled with pictures! ... (more)"

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2. Jenny

Walking for a living

Madison, WI, 53719

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

"Jenny was AMAZING! I booked last-minute (less than 1 week) and she was able to squeeze in a meet-and-greet with Hodge Podge before their scheduled drop-in. S... (more)"

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3. Crystal

Animal Lover

Middleton, WI, 53562

Drop-In Visits, Dog Walking

"I couldn't have asked for a better drop-in than Crystal! This was my first time using Rover and my first time leaving my sweet old dog with a stranger rather... (more)"

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4. Krysta

Summer is for the dogs!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Krystal went above and beyond my expectations! Caring for my dog as if her own. She would carry my 150+ pound senior mastiff in and out when his hips were hu... (more)"

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5. Cara

Apt life has me missing dog life!

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Cara was great! I knew from our initial meeting it was going to work. She was thorough with her questions and took notes. The was my first time using Rover v... (more)"

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6. Amy

Reliable & Conscientious Caretaker

Hill Farms-University Neighborh, madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Amy did a wonderful job! She was flexible last minute to watch/walk our lab on Thanksgiving. Our pup was nice & tired after his long walks. Would recommend ... (more)"

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7. Celia

Dogs big/cats small I love 'em all!

Madison, WI, 53705

Drop-In Visits, Dog Walking

"Celia provided great updates and photos of each visit. Our cats enjoyed the play time, head scratches, clean litter box, and feedings! Thanks again Celia, we... (more)"

Confirmed availability
4th of July
8. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

"Thank you so much! We love having Bruno spend time with you so we can relax and not worry about him. Thank you! (more)"

9. Ashley

Fun walks & fresh air for your dog!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

About: Hi there, I am Ashley! I have grown up with 5 dogs throughout my life and miss the constant energy! We have 2 cats currently that are quite active,... (more)

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10. Brenna

Graduate student animal lover!

Vilas, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"I really appreciated the help, photo and status that Brenna provided. She was comfortable with my high energy dog. (more)"

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11. Amy

Love and Patience!

Regent, Madison, WI, 53726

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

"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)"

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12. Mistie

Care + fun for your best friend

Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"Mistie is such a caring and beautiful person towards both animals and people. Your dog will be in excellent hands with her. I have known her for almost 10 ye... (more)"

13. Whitney

Reliable & caring dog/cat sitter!

Madison, WI, 53719

Drop-In Visits, Dog Walking

"Whitney was very conscientious when caring for Wrigley!!! (more)"

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14. Kristy

I'd love to walk your dog!

Madison, WI, 53705

Drop-In Visits, Dog Walking

"Kristy would be the first person I would ask to watch our dog (if we still had a dog) because Kristy loves dogs and finds amazing things about every single o... (more)"

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15. Holly

Will treat your pup as my own

Madison, WI, 53719

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

"Holly has provided great care for my puppy since I got him a few months ago. She watches him while I'm at work for the day and if I ever need her for night c... (more)"

Confirmed availability
4th of July
16. Gen

I'll love your dogs like you do!

Westhaven Trails, Madison, WI, 53719

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

"Gen came over to play with the pooch for a while when I had to be gone for 12+ horurs, and Paco seemed happy and playful when I returned. No problems at all... (more)"

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17. Jesse

25 yrs dogs/cats/horses/aggressive

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"While I was attending school I had to use jesse to watch my dog. Very affectionate with my dog and rain or shine the dog would get walked. Very punctual as... (more)"

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18. Hannah

Dog-tor in training!

Westmorland, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"Hannah was great, she sent plenty of pictures while we were away to let us know everything was going fine. (more)"

Confirmed availability
4th of July
19. Andrea

Around the clock care, fenced yard!

Sunset Village, Madison, WI, 53705

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

"Andrea really stepped in and helped me with Otis when I had to have surgery. She is always so good with Otis and he absolutely loves her. (more)"

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20. Cleda

I love dogs and they love me!

Spring Harbor, Madison, WI, 53705

Dog Boarding, Drop-In Visits, Dog Walking

About: I have a small dog myself and she is a diva. If I can handle her, I can handle any dog. We frequent the dog park and I've interacted with many dogs... (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:

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.