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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What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

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
37 reviews
12 repeat clients
from
$18
per visit

Melinda was a great help and took great care of our pup during her check-ins. She was timely and is a great communicator. We’ll definitely ask her for help in the future!

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
41 reviews
10 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: 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

She did a great job taking my cat to the vet and bringing him home. She communicated super fast and sent pictures. I will for sure use her again!

Sitter Profile Image: Ann V.
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Sitter Profile Image: Ann V.
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4. Ann V.

Animal Lover and Law Student
Madison, WI, 53711
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
30 reviews
8 repeat clients
from
$20
per visit

Ann was fantastic with our cat and kept us updated with tons of photos and detailed report cards while we were on vacation. We’d rebook with her in a heartbeat!

Sitter Profile Image: Kim M.
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Sitter Profile Image: Kim M.
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5. 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

Once again, I am incredibly happy with the care Kim provides to my fur babies. She’s the type of sitter I’d rearrange a trip for to ensure she’s available to watch after my kittens. Can’t recommend her enough!

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 was available on super short notice (just a few hours) when our dog-walker fell through; our dogs love her and it was so great knowing we didn't have to worry about the dogs during our day away from home. She's great!!!

Sitter Profile Image: Sara J.
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Sitter Profile Image: Sara J.
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7. 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

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.

Sitter Profile Image: Lydia S.
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Sitter Profile Image: Lydia S.
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8. 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
43 reviews
16 repeat clients
from
$19
per visit

Lydia was a great communicator and very thorough sitter. She followed directions for providing medication perfectly. She also went above and beyond the simple requested drop in for our kitty's basic needs and provided plenty of attention and love. We will absolutely be booking again.

Sitter Profile Image: Jennifer L.
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Sitter Profile Image: Jennifer L.
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9. Jennifer L.

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

Jennifer is awesome. Our plans changed the morning of travel & we could no longer take our dog with. Jennifer made herself available for us & was able to let Rayna out. We were so grateful for her flexibility and willingness to care for our pooch.

Sitter Profile Image: Allegra R.
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Sitter Profile Image: Allegra R.
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10. 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

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!

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
27 reviews
9 repeat clients
from
$24
per visit

Return customer here!! Jess was so great with my cat. My cat isn’t a fan of new people (she still hides from people she’s known for months) YET Jess was able to get her to warm up enough for some pets. I really appreciated her pictures and descriptions for each visit. My cat was well taken care of and I plan to use Jess as my petsitter the next time I’m away.

Sitter Profile Image: Corinne B.
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Sitter Profile Image: Corinne B.
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12. Corinne B.

Animal Lover
Madison, WI, 53719
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
15 reviews
6 repeat clients
from
$20
per visit

Corinne is quick to respond to messages and very personable. She did a great job with our almost 12 yo rescue dog!

Sitter Profile Image: Claire D.
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Sitter Profile Image: Claire D.
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13. 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
4 reviews
1 repeat client
from
$20
per visit

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!

Sitter Profile Image: Azaria O.
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Sitter Profile Image: Azaria O.
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14. Azaria O.

Pets don’t need us, we need them🙂
Verona, WI, 53593
3.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
44 reviews
16 repeat clients
from
$20
per visit

Great job. My guy was super happy and seemed comfortable. He got to go out a lot too! She took tons of pictures and was easy to get ahold of.

Sitter Profile Image: Dietrich G.
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Sitter Profile Image: Dietrich G.
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15. 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
19 reviews
4 repeat clients
from
$12
per visit

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: Cindy D.
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Sitter Profile Image: Cindy D.
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16. 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: Samantha K.
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Sitter Profile Image: Samantha K.
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17. 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
25 reviews
9 repeat clients
from
$20
per visit

We love booking Samantha when she is available. She is always friendly, kind, and does a fantastic job taking care of our cat when we are away. Thanks Samantha for being such a gem!

Sitter Profile Image: Cleda W.
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Sitter Profile Image: Cleda W.
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18. 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

Thank you for watching felix! Cleda communicates well, very thoughtful and loves animals:) she always leaves a thorough summary each day about your pet and how the visit went. I definitely would recommend Cleda hands down no worries with her at will. Thanks again!

Sitter Profile Image: Whitney H.
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Sitter Profile Image: Whitney H.
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19. 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

Whitney was amazing! She was thorough and sent some great pictures— definitely something you need when you’re leaving your pets with someone new. Would highly recommend!

Sitter Profile Image: Bailee B.
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Sitter Profile Image: Bailee B.
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20. Bailee B.

Time with pets is time well spent.
Sauk Creek, Madison, WI, 53717
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$20
per visit

We are so grateful for Bailee who took good care of our dog, Layla, on Easter Sunday. We have used Bailee before and will definitely use her again.

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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