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.

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

Search Results

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Stacy & Jackson M.
Experienced Cat SittersMeadowood, Madison, WI, 53711
House Sitting, Drop-In Visits

Jackson and Stacy have watched my two kitties while I've been away a couple of times. They are reliable, communicative, and took great care of my little furry f… (more)

from
$15
per visit
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Cassie G.
2.
Certified Dog LoverMiddleton, WI, 53562
Drop-In Visits, Dog Walking

Cassie is great! This is the second time she’s come to take care of my dog and cat and she does and awesome job! I love the updates after each visit and my pets… (more)

from
$13
per visit
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Ashley E.
3.
Treating Your Furbabies Like My OwnMadison, WI, 53705
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

We loved getting Ashley’s detailed updates and photos while we were away. Ashley learned all of our pets’ quirks (favorite toys, weird eating habits), and knowi… (more)

from
$18
per visit
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Ilise M.
4.
Company for Your Furbaby!Orchard Ridge Community, Madison, WI, 53711
Drop-In Visits, Doggy Day Care, Dog Walking

Ilise is awesome! She provides timely communication and took great care of my two large dogs. I will definitely use her service again. (more)

from
$13
per visit
Calendar Recently Updated
McKenna A.
20+ yrs experience with all breeds!Blackhawk, Middleton, WI, 53562
Drop-In Visits

McKenna was amazing with our little puppy! So caring, thoughtful, and flexible. Great to know our four legged family member was in such good hands! (more)

from
$15
per visit
Confirmed availability: Labor Day
AVAILABLE THIS WEEKEND!!!Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking

Jennifer took wonderful care of my cat while I was out of town over the holidays. She sent me photos and updates daily, and even got my cat a Christmas gift! … (more)

from
$20
per visit
Calendar Recently Updated
Will treat them like family!Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking

About: Hi! I’m Lindsey and I would love to take care of your pup. I’ve owned 2-3 dogs my whole life with my family. We’ve had labs, lots of mixed unknown br… (more)

from
$13
per visit
Confirmed availability: Labor Day
Caring, experienced and reliable!Summit Woods, Madison, WI, 53711
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Hillary was attentive, kind and so great with Rex!! Her check-ins included lots of photos and details of how it went which was so so helpful as I’m a very worri… (more)

from
$25
per visit
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9.
The best care for your best friend!Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking

Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone! (more)

from
$12
per visit
10.
Love to cuddle and spoil your petsMeadowood, Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking

Briana is a natural when it comes to pet care! She has been a compassionate animal owner and care taker of many animals- from reptiles, horses, cats to dogs! … (more)

from
$15
per visit
Calendar Recently Updated
11.
Going above & beyond for your dog!Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking

Thank you so much for the last minute great care!! (more)

from
$17
per visit
Confirmed availability: Labor Day
12.
Enthusiastic Dog LoverPrairie Hills, Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking

Kagen has been watching Juno for me on and off for about a year now. She’s one of the few people my kitty trusts fully and gladly welcomes into our home. I’m ve… (more)

from
$20
per visit
Calendar Recently Updated
13.
Dog owner & med student!Spring Harbor, Madison, WI, 53705
Drop-In Visits, Doggy Day Care, Dog Walking

Sophie is a wonderful sitter who cares so much about animals. She has a lot of experience with caring for dogs and just genuinely loves them. She also did a gre… (more)

from
$18
per visit
Calendar Recently Updated
Stay-cation with us!Skyview Meadows, Madison, WI, 53719
Dog Boarding, House Sitting, Drop-In Visits
2 years of experience

About: I’ve grown up around dogs- I currently have my own rescue who would LOVE to have a friend to hang out with you. He’s the sweetest boy to all, so all … (more)

from
$17
per visit
15.
Reliable & caring dog/cat sitter!Madison, WI, 53719
Drop-In Visits

Whitney has visited my 4 year old cat Clark on multiple occasions. On the most recent, I had to go away for the weekend, and Clark had gotten sick a few times e… (more)

from
$16
per visit
Calendar Recently Updated
16.
Not enough dogs in my lifeMadison, WI, 53705
Drop-In Visits, Dog Walking

Shelbi is a fantastic caregiver - Shelbi cared for our 3 year old German Shepherd while we were in the hospital during the birth of our daughter. Zeus warmed … (more)

from
$15
per visit
Calendar Recently Updated
17.
Any Animal, Any TimeMadison, WI, 53711
Drop-In Visits, Dog Walking

anthony took great care of my cat and sent me some adorable pictures! he also helped navigate a weird apartment situation. very happy with my choice of cat sitt… (more)

from
$14
per visit
Calendar Recently Updated
18.
Best friend for your fur baby!Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking

Ciara is the perfect pet sitter! She loves animals and is very responsible. She has pet sit for me before and has done an excellent job :) (more)

from
$15
per visit
19.
Cat lover and responsible workerMadison, WI, 53717
House Sitting, Drop-In Visits

Sarah was amazing with our two cats! She spent quite a lot of time with each of them, provided detailed updates twice daily, and played with both our older and … (more)

from
$15
per visit
20.
Perfectly sane cat lady!*Madison, WI, 53711
Drop-In Visits

Anna was excellent! We absolutely loved having her take care of our cat Jake while we were on vacation for a week. She was so attentive—even taking care of an a… (more)

from
$20
per visit

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: