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. Crystal

Animal Lover

Middleton, WI, 53562

Drop-In Visits, Dog Walking

25 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)"

2. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

12 repeat clients

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

3. Krysta

Summer is for the dogs!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I couldn't think of anyone better to watch my pet. Krysta has been around animals her whole life to include her own two dogs growing up, helping her family a... (more)"

4. Celia

Dogs big/cats small I love 'em all!

Madison, WI, 53705

Drop-In Visits, Dog Walking

11 repeat clients

"Celia was fantastic to work with! When something came up with her schedule and we needed to make adjustments, she let me know right away and I truly felt so ... (more)"

5. Amy

Reliable & Conscientious Caretaker

Hill Farms-University Neighborh, madison, WI, 53705

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

10 repeat clients

"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)"

6. Sarah

Looking to meet some furry friends!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah has watched my dog for me several times while I was away on vacation for a few days. She has always taken good care for him, taking him for a walk at l... (more)"

7. Brenna

Graduate student animal lover!

Vilas, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

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

Confirmed Memorial day Availability
8. Kristy

I'd love to walk your dog!

Madison, WI, 53705

Drop-In Visits, Dog Walking

4 repeat clients

"I have left 2 dogs in Kristy's care in the past and have been very pleased with her conscientious care for my pets. Upon my return, they were very happy and... (more)"

9. Kiersten

Corgis are my spirit animal.

Regent, Madison, WI, 53726

Drop-In Visits, Dog Walking

6 repeat clients

"I would recommend Kiersten to everyone! She has come and seen our puppy several times. She is extremely reliable and flexible. We are so lucky to have found ... (more)"

10. Jesse

25 yrs dogs/cats/horses/aggressive

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

Confirmed Memorial day Availability
11. Gen

I'll love your dogs like you do!

Westhaven Trails, Madison, WI, 53719

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

13 repeat clients

"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)"

12. Andrea

Around the clock care, fenced yard!

Sunset Village, Madison, WI, 53705

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

77 repeat clients

"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)"

Confirmed Memorial day Availability
13. Hannah

Dog-tor in training!

Westmorland, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"Hannah had looked after both my cat and dog, Sir Matthew and Juno, for years and I've never had a complaint. Hannah is highly personable with my family and a... (more)"

14. Cleda

I love dogs and they love me!

Spring Harbor, Madison, WI, 53705

Dog Boarding, Drop-In Visits, Dog Walking

5 repeat clients

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)

15. 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)"

16. Whittney

Love dogs with a passion!

High Point Estates, Madison, WI, 53719

Drop-In Visits, Dog Walking

1 repeat client

"I've had Whittney watch my two small dogs. One has a heart mumor and needs a little extra love. She made sure she understood how to give my Chihuahua her med... (more)"

Confirmed Memorial day Availability
17. Kaylin

Pick me for your Critter/Cat needs!

Oakbridge Community, Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"We've been using Kaylin as a pet sitter for our senior cat (Halle Berry) for a few years now and could not be happier! Kaylin is friendly, dependable, and al... (more)"

Confirmed Memorial day Availability
18. Jennifer

AVAILABLE THIS WEEKEND!!!

Madison, WI, 53719

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

11 repeat clients

"Jennifer is super and very reliable! She's really great about being flexible and working with our schedule. I was out of town and needed an extra stay. I had... (more)"

19. Eden

I’ll run with your dog!

Wexford, Madison, WI, 53717

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

About: Hi, I’m Eden! I’m an animal lover who will love your dog endlessly! Whether your need a pet sitter, dog walker, or house sitter, I will take offers... (more)

20. Matthew & Rachael

Top-Notch Professional Pet Services

Madison, WI, 53719

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

4 repeat clients

"Matt is a passionate dog lover! I would trust him with my dog which is saying a lot becuase my dog loves to run away and actively pursues the challenge of g... (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: