Pet Sitting & Drop Ins in High Crossing, 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.
Confirmed availability: Memorial day
Jennifer P.
Dogs are my favorite people!!McFarland, WI, 53558
House Sitting, Drop-In Visits, Dog Walking

Such a cold week! Thankfully it was warmed by knowing I'd have a wonderful sitter to come check on my pugs! Jennifer braves the cold and checks on my babies and… (more)

from
$13
per visit
Calendar Recently Updated
Kerri M.
2.
Canine Therapy - Nothing Better!!Windsor, WI, 53598
Drop-In Visits, Dog Walking

Kerri is so great! She’s been watching our puppy for a couple of months now and we love her. She brought Oliver a bunch of toys that her dog doesn’t play with a… (more)

from
$14
per visit
Calendar Recently Updated
Michel P.
3.
Certified Vet Tech & Animal Lover!Sun Prairie, WI, 53590
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Michel was great. Took great care of my cats! (more)

from
$20
per visit
Colleen & Micheal K.
Responsible & Loving Pet SitterHeistand, Madison, WI, 53714
House Sitting, Drop-In Visits, Dog Walking

This was the first time I had Colleen do a drop-in visit and it went perfectly!! The boys always look forward to seeing her ❤️ Colleen is always super thoughtfu… (more)

from
$18
per visit
Confirmed availability: Memorial day
Abby F.
5.
Any dog, any size, happy and tired!Glendale, Madison, WI, 53716
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Great sitting experience with Abby! We got 4 cute fur baby photos a day and I felt like my kitties were in good hands. Came home to clean bowls and boxes! 10/10… (more)

from
$15
per visit
Calendar Recently Updated
6.
Here to make your animal happy 🐶Ridgewood, Madison, WI, 53704
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jaren is the most caring, kind energetic individual who deeply loves dogs and cats and all animals. He is very health minded and loves to take hikes/walks with… (more)

from
$12
per visit
Confirmed availability: Memorial day
7.
Individualized, customized pet careEken Park, Madison, WI, 53704
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Anna is very nice and was very professional. My cats seemed to like her and she treated them well. She sent lots of pictures. I will book with Anna again in t… (more)

from
$19
per visit
Confirmed availability: Memorial day
Loving, Veterinary Nurse ❤️Sherman Village, Madison, WI, 53704
Dog Boarding, Drop-In Visits, Dog Walking

Christine is great at taking the best care of my puppy while I am at work! She always sends me at least two pictures each visit. She is very attentive to detail… (more)

from
$20
per visit
Confirmed availability: Memorial day
9.
I'm just as excited for walkies.Ridgewood, Madison, WI, 53704
House Sitting, Drop-In Visits, Dog Walking

Gigi is a great pet owner. She is punctual and responsible and there's no need to worry about your pet in her hands. She loves all sorts of animals - especially… (more)

from
$20
per visit
Calendar Recently Updated
10.
15 Years of Pet Lovin'!Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53704
Drop-In Visits, Dog Walking

Jessica is always so quick to respond, thoughtful and is great with Catdog! Goes above and beyond, giving him time to sit on the porch (his favorite) and is sup… (more)

from
$15
per visit
Confirmed availability: Memorial day
11.
Passionate animal lover!Bluff Acres, Madison, WI, 53704
House Sitting, Drop-In Visits, Dog Walking

Unfortunately I did not get the chance to meet Brea in person since I needed a last minute sitter, but she was extremely accommodating with scheduling drop ins,… (more)

from
$15
per visit
Calendar Recently Updated
12.
Responsible, experienced student!High Crossing, Madison, WI, 53718
Drop-In Visits, Dog Walking

Dropped by to feed and let my two dogs out while I was gone for a long day. Seems like they got just what they needed, including some play! (more)

from
$14
per visit
13.
Responsible, active, pet ownerCottage Grove, WI, 53527
Dog Boarding, Drop-In Visits

This was our first time using Rover and we were very happy with Amanda! She was prompt, made sure our two dogs played and had fun, and sent pics of her drop in … (more)

from
$12
per visit
14.
Your pets new furrever best friend!Madison, WI, 53718
House Sitting, Drop-In Visits, Dog Walking

Jaime did such a great job taking care of my dog while I was gone for a week! She dropped in twice a day and every time sent a nice detailed update with photos.… (more)

from
$14
per visit
Calendar Recently Updated
15.
Loving pet sitterMadison, WI, 53718
House Sitting, Drop-In Visits, Dog Walking

Sandy has always been super helpful in taking my dog Hester for a walk when things came up at work and I was not able to. He is a larger dog but she is still a… (more)

from
$12
per visit
16.
Max 
Verified Background Check
Can walk or drop in during day!Reston Heights, Madison, WI, 53718
House Sitting, Drop-In Visits, Dog Walking

Max is nothing short of amazing! He was very accommodating and flexible with drop-in visits for my dog. 10/10 happy with his help and 10/10 would recommend him … (more)

from
$12
per visit
17.
Any dog, any size, any temperamentMcClellan Park, Madison, WI, 53718
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sarah was able to help us out on very short notice. She did an excellent job stopping by a few times to let our pup outside on walks and provided dinner and me… (more)

from
$15
per visit
Calendar Recently Updated
18.
Active and fun animal loverRidgewood, Madison, WI, 53704
House Sitting, Drop-In Visits, Dog Walking

About: Hi, my name is Olivia and I am a college student at Madison Area Technical College. I was looking for extra money so I figured why not do something I… (more)

from
$18
per visit
Confirmed availability: Memorial day
19.
Understanding and flexible careHeistand, Madison, WI, 53714
Drop-In Visits, Dog Walking

Sarah is a true animal lover! She went above and beyond for our pup - getting him out for a walk, playing in the backyard, and making sure he got his meal. I'… (more)

from
$12
per visit
Calendar Recently Updated
Flexible and Caring Animal LoverMadison, WI, 53718
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Isabella is great with my family’s pets! She is reliable and trustworthy and always our first choice when my family needs a pet sitter. Definitely recommend Isa… (more)

from
$15
per visit

Rover also offers Pet Sitting & Drop Ins in:

Dog owners in High Crossing, Madison, WI turn to pet sitters on Rover.com for their pet sitting needs. Over 423 pet owners have reviewed pet sitters in Madison, giving them an average rating of 4.9/5. Pet sitting can be affordable, no matter where you live or what your price range may be. Curious about how much pet sitting costs in Madison with Rover.com? Check out our average pet sitting rates near you to get an idea before getting a conversation started with a pet sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect High Crossing, 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 High Crossing, 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 High Crossing, 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: