Pet Sitting & Drop Ins in Woodland Hills, 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
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Sitter Profile Image: Melinda N.
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Sitter Profile Image: Melinda N.
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1. Melinda N.

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

This was my first time using a paid service to take care of my cats, and I am so happy with Melinda. She spent time with them and took great pictures of my boys, which I looked forward to every day I was gone. She was wonderfully respectful of my home. I would gladly book her services again.

Confirmed availability: Juneteenth
Sitter Profile Image: Seán & Leticia W.
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Sitter Profile Image: Seán & Leticia W.
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2. Seán & Leticia W.

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

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.

Confirmed availability: Juneteenth
Sitter Profile Image: Maiya W.
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Sitter Profile Image: Maiya W.
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3. Maiya W.

I'll love them like you love them!
Middleton, WI, 53562
1.6 mi. away
Drop-In Visits
5.0 out of 5 stars
78 reviews
29 repeat clients
from
$15
per visit
Profile image

First time I’ve had Maiya or anyone from Rover care for out cat…she faithfully showed up each day and made friends with Beau. She did e aptly what we asked. She was perfect for our needs. So grateful!

Sitter Profile Image: Allegra R.
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Sitter Profile Image: Allegra R.
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4. Allegra R.

Rover 101
Dog person for life.
Faircrest, Madison, WI, 53705
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
53 reviews
21 repeat clients
from
$25
per visit
Profile image

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!

Confirmed availability: Juneteenth
Sitter Profile Image: Krista C.
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Sitter Profile Image: Krista C.
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5. Krista C.

I've never met a pet I didn't LOVE!
Verona, WI, 53593
3.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$15
per visit
Profile image

Krista was awesome! One of my cats can be a little anxious and unwelcoming to new people, and Krista did a perfect job of following my instructions to accommodate him. By the end, I could see in the daily pictures that my cat really warmed up to her. I'll definitely be requesting cat care from Krista again!

Sitter Profile Image: Kim M.
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Sitter Profile Image: Kim M.
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6. Kim M.

Loving and experienced Dog Mom!
Middleton, WI, 53562
1.2 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
94 reviews
40 repeat clients
from
$17
per visit
Profile image

Kim was our first experience using Rover and she was wonderful. She explained how things worked and we met beforehand to go over things. Kim took so much stress away from our trip. Besides taking care of the cats, it's nice that she was there to check on the house as well. Thank you Kim!

Confirmed availability: Juneteenth
Sitter Profile Image: Dietrich G.
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Sitter Profile Image: Dietrich G.
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7. Dietrich G.

Dietrich is a dog's delight
Walnut Grove, MADISON, WI, 53717
0.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
25 reviews
5 repeat clients
from
$12
per visit
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Dietrich has been a wonderful dogsitter for my dog! He is a great communicator thru the Rover App and I appreciate is daily comments and photo. I know that Coco is in great care!

Sitter Profile Image: Danielle M.
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Sitter Profile Image: Danielle M.
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8. 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
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Danielle was awesome! Remy thoroughly enjoyed having her take care of him! His attitude after she came to visit was satisfying! We'll continue to ask her to care for Remy!

Confirmed availability: Juneteenth
Sitter Profile Image: Lydia S.
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Sitter Profile Image: Lydia S.
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9. Lydia S.

Here to help with your schedule
Middleton, WI, 53562
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
46 reviews
17 repeat clients
from
$19
per visit
Profile image

Lydia took great care of my kitties! While I was gone she captured some really cute pics, and when I got home they were obviously well taken care of.

Confirmed availability: Juneteenth
Sitter Profile Image: Jennifer L.
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Sitter Profile Image: Jennifer L.
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10. Jennifer L.

Rover 101
AVAILABLE THIS WEEKEND! TOP RATED!
Madison, WI, 53719
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
288 reviews
107 repeat clients
from
$22
per visit
Profile image

A few days before we left on our trip, one of our cats started having seizures. We soon learned she was quite sick with end stage cancer. I had originally planned to have her at the vet for the weekend, but with her new prognosis, they suggested we try and keep her at home. Jennifer didn’t even hesitate (even knowing how sick Luna was) and booked very last minute. I felt comfortable knowing she had vet tech experience and even brought our kitties some treats. Would highly recommend Jennifer!

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Sitter Profile Image: Jess B.
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Sitter Profile Image: Jess B.
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11. Jess B.

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

Jess gives the absolute best updates during drop-in visits. The level of care and detail she puts into her write-ups and pictures is unmatched, and my dog just loves her.

Confirmed availability: Juneteenth
Sitter Profile Image: Claire D.
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Sitter Profile Image: Claire D.
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12. Claire D.

Rover 101
Pet Care by Claire!
Blackhawk, Madison, WI, 53717
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
1 repeat client
from
$20
per visit
Profile image

Claire was wonderful taking care of my cats. She provided timely, thorough and thoughtful updates and made me feel reassured that my babies were well. I could tell she was paying attention to the details I had provided on likes and was incorporating them into visits and trying to make them happy. I would definitely recommend Claire and will ask her for help again when needed!

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Sitter Profile Image: Whitney H.
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Sitter Profile Image: Whitney H.
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13. Whitney H.

Rover 101
Reliable & caring dog/cat sitter!
Madison, WI, 53719
2.0 mi. away
Drop-In Visits
5.0 out of 5 stars
30 reviews
16 repeat clients
from
$19
per visit
Profile image

I messaged Whitney at the absolute last minute because I realized I forgot to get someone to check in on my kitty while we were out of town for Thanksgiving. Whitney replied quickly and said she’d be happy to help while we were away— what a relief! She was great and my skittish cat was happy to come out and get some pets from her. Will definitely book Whitney again!

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Sitter Profile Image: Sara J.
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Sitter Profile Image: Sara J.
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14. Sara J.

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

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: Taylor R.
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Sitter Profile Image: Taylor R.
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15. Taylor R.

Professional fury baby spoiler!
Madison, WI, 53719
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
6 repeat clients
from
$22
per visit
Profile image

Taylor took great care of my pup! She is super sweet and dependable!! My pup was super happy and loved Taylor

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Sitter Profile Image: Cleda W.
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Sitter Profile Image: Cleda W.
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16. Cleda W.

Rover 101
Dogs & Cats LOVE me!
Madison, WI, 53705
1.3 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
164 reviews
75 repeat clients
from
$20
per visit
Profile image

Cleda is excellent. Extremely communicative, great at winning over (even shy) pets, and provides detailed updates that show the passion she has for providing top quality care. I would highly recommend Cleda!

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Sitter Profile Image: kylie l.
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Sitter Profile Image: kylie l.
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17. kylie l.

Can’t wait to meet your dogs!
Madison, WI, 53705
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$15
per visit

Kylie is a very responsible person. She is very caring when she is watching my kids and my dogs, I have no worries when she is watching them.

Confirmed availability: Juneteenth
Sitter Profile Image: Lindsey C.
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Sitter Profile Image: Lindsey C.
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18. Lindsey C.

I used to call myself the Dog Queen
Madison, WI, 53705
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$15
per visit

Lindsey is an incredible pet sitter!! She is attentive, compassionate, and goes above and beyond every time. It can be anxiety-inducing to leave your pet behind on a vacation, but whenever Lindsey has watched my cat, I know he is safe, healthy, happy, and very well loved. On top of that, Lindsey is an excellent communicator, is highly organized, and overall, is an absolute joy to work with. I truly cannot recommend her enough!!

Sitter Profile Image: Samantha K.
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Sitter Profile Image: Samantha K.
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19. Samantha K.

I’ll take good care of your buddies
Middleton, WI, 53562
1.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
9 repeat clients
from
$20
per visit
Profile image

Samantha provided absolutely awesome care for my kitties!! She provided ample time for care, play time and just goofin with Potato and Squiggy!!! Loved the pictures and updates!!! I know that they were in great hands while I was out of town!! Thank you again Samantha!!

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Sitter Profile Image: Alisyn L.
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Sitter Profile Image: Alisyn L.
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20. Alisyn L.

Veterinary Technician & Adventurer
Walnut Grove, Madison, WI, 53717
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
15 repeat clients
from
$25
per visit
Profile image

Alisyn did an awesome job with my cat Cleo. She was quick to respond to messages and sent lots of pictures. She even gave her a little Christmas present!

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

Rover also offers other services in Woodland Hills:

Dog owners in Woodland Hills, 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.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Woodland Hills pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Woodland Hills, Madison, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Woodland Hills pet sitters and avoid the kennel.

Drop-In Visits