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.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

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Sitter Profile Image: Seán & Leticia W.
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Sitter Profile Image: Seán & Leticia W.
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1.

Seán & Leticia W.

Rover 101
Take Care Of Your Best Friend!
Maple-Prairie, Madison, WI, 53719
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
6 repeat clients
from
$16
per visit

Seán & Leticia were great to work with for my first time using Rover. They were respectful of my very nervous cat and took great pictures of my friendlier cat! Seán helped adjust the dates of my booking and checked in with me often to make sure he had all the details right.

Sitter Profile Image: Ashley E.
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Sitter Profile Image: Ashley E.
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2.

Ashley E.

Treating Your Furbabies Like My Own
Madison, WI, 53705
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
363 reviews
113 repeat clients
from
$26
per visit

Ashley has been doing drop-in visits for our cats since we moved to Madison last year, and we are glad to have someone we can rely on. In addition to the planned feeding and care, she has dealt with unexpected situations as they come up and we have never had to worry about our cats or our home.

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Sitter Profile Image: Melinda N.
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Sitter Profile Image: Melinda N.
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3.

Melinda N.

Sorry I was late. I saw a dog!
Maple-Prairie, Madison, WI, 53719
2.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
31 reviews
10 repeat clients
from
$18
per visit

Spunky enjoy her time with Melinda

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Sitter Profile Image: Brianna V.
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Sitter Profile Image: Brianna V.
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4.

Brianna V.

Energetic Fur Baby Lover 🥰
Madison, WI, 53593
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$13
per visit

Bri has been an exceptional person to provide care for pets throughout the years! She will house/pet sit for me when I leave for vacation and would care for my 2 boxers, chihuahua, and cat. She would take them for walks, play with them, follow all of my instructions while away, and left my house clean. She is reliable and trustworthy. She would send me pupdates of my dogs while away!

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Sitter Profile Image: Jess B.
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Sitter Profile Image: Jess B.
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5.

Jess B.

Your weekend/evening needs covered!
Madison, WI, 53719
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
9 repeat clients
from
$24
per visit

Jess did a great job taking care of my cat! My cat hides from new people, and she still took the time to find her and send me a photo. The updates she wrote with each check-in always made me so happy. I had to rush and change my travel plans and she was incredibly accommodating, helpful, and was able to change my booking to reflect my new travel dates! I would highly recommend Jess to take care of your pets.

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Sitter Profile Image: Danielle M.
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Sitter Profile Image: Danielle M.
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6.

Danielle M.

I am dog's best friend!
Verona, WI, 53593
3.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
37 repeat clients
from
$12
per visit

Danielle is simply awesome!! We can always trust and count on Danielle to show up when scheduled and to take wonderful care of our boy, Gus!!

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Sitter Profile Image: Louisa M.
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Sitter Profile Image: Louisa M.
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7.

Louisa M.

Your pet’s new friend! 🐶🐱🐰🐔🐠
Midvale Heights Community, Madison, WI, 53711
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
33 reviews
12 repeat clients
from
$25
per visit

Louisa was exceptional. We reached out at the last minute over a holiday weekend and she was very accommodating and helpful. She was conscientious, punctual and loved our large dog lots. She sent Rober and text updates, pictures and was easily reachable whenever we needed. We won’t hesitate to have her dog sit when needed again!

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Sitter Profile Image: Allegra R.
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Sitter Profile Image: Allegra R.
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8.

Allegra R.

Rover 101
Dog person for life.
Madison, WI, 53705
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
47 reviews
18 repeat clients
from
$25
per visit

My dogs really like Allegra and she seems to be great with them too. She was great during our meet and greet and spent time to get to know the pups. Will hire again for sure!

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Sitter Profile Image: Dietrich G.
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Sitter Profile Image: Dietrich G.
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9.

Dietrich G.

Dietrich is a dog's delight
Walnut Grove, MADISON, WI, 53717
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
3 repeat clients
from
$12
per visit

Dietrich is wonderful!

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Sitter Profile Image: Shaina N.
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Sitter Profile Image: Shaina N.
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10.

Shaina N.

Animal-loving Madisonian
Midvale Heights Community, Madison, WI, 53711
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$25
per visit

Shaina left me feeling very comfortable about having her drop in for visits with my kitties. I feel as if she treated them like her own and was very thorough during her time spent. I feel like I could also tell a difference with the cats demeanor when I arrived back home as well; they didn’t seem as anxious as in the past with using another service. Thank you Shaina!

Sitter Profile Image: Sara J.
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Sitter Profile Image: Sara J.
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11.

Sara J.

I’ll take care of your PAWfect pup
Junction Ridge, Madison, WI, 53717
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
19 reviews
4 repeat clients
from
$25
per visit

Sara has been timely with her drop in visits, flexible with the craziness of having to exchange keys, and communicative! We appreciate (including Maverick) her greatly with our long work hours.

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Sitter Profile Image: Isabelle B.
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Sitter Profile Image: Isabelle B.
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12.

Isabelle B.

Lifelong pet caretaker since 6
Madison, WI, 53719
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
19 years of experience
from
$13
per visit

About: I grew up with a cat and a yellow lab. I have experience introducing new animals to existing pets and new environments. I like to think I can interpret their body language and spoken cues closely, and know how to interact accordingly. I have experience with training behavioral concerns in cats, administering oral and eye medications, cleaning ears, grooming and skin care, and general feeding and play, including the difficult task of serving up wet food to impatient kitties. I am currently working part-time, so my schedule is open and flexible outside of my work schedule. I would find overnight stays and daytime check-ins easily manageable and can prioritize your pet in my schedule. At this time, I am only offering client home services, but I would be sure to spend time playing with and caring for any companions I am charged with to ensure quality time for the pet and the owner.

Sitter Profile Image: Jennifer L.
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Sitter Profile Image: Jennifer L.
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13.

Jennifer L.

Rover 101
AVAILABLE THIS WEEKEND! TOP RATED!
Madison, WI, 53719
1.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
261 reviews
91 repeat clients
from
$22
per visit

Jennifer is great. She took great care of my dogs. She made sure to keep my floor clean while my dogs occasionally pee/poop on the floor. She also kept an eye on my dogs when they eat so that they don’t steal each other’s food. I will definitely let Jennifer take care for my dogs again!

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Sitter Profile Image: Brian C.
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Sitter Profile Image: Brian C.
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14.

Brian C.

Proud owner of a blind handsome dog
Prairie Hills, Madison, WI, 53711
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$15
per visit

Great guy! He was super friendly and and just a great person overall. He took my dog on a walk for longer than I requested and my puppy dog loved it! He’s dependable and my dog loves him. You. And you can’t argue with that!! :)

Sitter Profile Image: Jocelyn C.
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Sitter Profile Image: Jocelyn C.
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15.

Jocelyn C.

I’ll care for yours like my own!
Madison, WI, 53705
1.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$20
per visit

Excellent, will use again!

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Sitter Profile Image: Ilise M.
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Sitter Profile Image: Ilise M.
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16.

Ilise M.

Company for Your Furbaby!
Orchard Ridge Community, Madison, WI, 53711
1.6 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
34 reviews
10 repeat clients
from
$15
per visit

It can be so hard leaving one's pets, but Ilise made the guilt and stress of it so much lessened. She was flexible and went above and beyond when some issues at my house came up. I can highly recommend hiring her, she is thoughtful, conscientious and very kind. We feel so grateful to have had someone caring and trustworthy be there when we couldn't. Thank you, Ilise!

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Sitter Profile Image: Emme H.
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Sitter Profile Image: Emme H.
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17.

Emme H.

Patient Pet Playmate! (Day Avail.)
Midvale Heights Community, Madison, WI, 53711
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
33 reviews
11 repeat clients
from
$25
per visit

Emme was great! She was flexible with our schedule the day of her drop in visit and was thoughtful enough to give Max something to occupy himself while she left so he wouldn’t notice as much.

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Sitter Profile Image: Cindy D.
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Sitter Profile Image: Cindy D.
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18.

Cindy D.

Happy to Love your Small Dog!
Madison, WI, 53717
1.4 mi. away
House Sitting, Drop-In Visits
4.5 out of 5 stars
4 reviews
1 repeat client
from
$15
per visit

Cindy has taken care of my pets through the years and has been a dog lover since I have known her. She prides herself in routinely feeding them, taking them for walks and interacting with them to make sure they’re happy. I trust her the most out of anyone to take care of my animal family members!

Sitter Profile Image: Hannah S.
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Sitter Profile Image: Hannah S.
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19.

Hannah S.

Love to check on your fur babies!
Madison, WI, 53711
1.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
62 reviews
33 repeat clients
from
$20
per visit

This was the second time Hannah watched our cat for us, this time for a whole week. Our cat was well taken care of and I appreciated getting updates every visit. Hannah even noticed all our cat’s little habits, making me feel confident that she was being well cared for!

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Sitter Profile Image: Cameron R.
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Sitter Profile Image: Cameron R.
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20.

Cameron R.

Helping care for your best friend
Madison, WI, 53705
1.2 mi. away
Drop-In Visits, Dog Walking
1 review
from
$15
per visit

Cameron has been an animal lover all her life! She grew up taking care of her pets, faithfully walking her dogs each day and tending to their needs for love and attention. It's no wonder she is studying to be a veterinarian at the University of Wisconsin, Madison. Not only does she have compassion for animals, but Cameron is one of the hardest workers I know. You can depend on her reliability and trust that she will follow through on her commitments to you and your pets.

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Rover also offers Pet Sitting & Drop Ins in these neighborhoods:

Rover also offers other services in Oakwood Village:

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:

Drop-In Visits