Pet Sitting & Drop Ins in Woodlands, 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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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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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
4.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
36 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!

Confirmed availability: Memorial Day Weekend
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
40 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.

Confirmed availability: Memorial Day Weekend
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
1.7 mi. away
Drop-In Visits
5.0 out of 5 stars
78 reviews
29 repeat clients
from
$15
per visit

Maiya was awesome with our needy cat! He wants all the attention all the time and she was sure to give him lots of love while we were out of town. She offered to bring in the mail too! Such a nice women and definitely a true animal lover!

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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
3.4 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 my favorite cat sitter we’ve gotten from rover thus far. She was incredibly thorough in her reports and I looked forward to all the pictures we got of the cats each day. She was able to give our stubborn cat his medicine each day with no issues and followed instructions to a tee. Will definitely be booking with her again in the future!

Sitter Profile Image: Danielle M.
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Sitter Profile Image: Danielle M.
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5. 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 awesome!! I am so lucky to have her as a sitter for Piper. Piper absolutely adores her and looks forward to every visit. Danielle is great with her and always keeps you updated on your dog. I honestly couldn't go to work without worries if it wouldn't be for her. Knowing that she is taking care of Piper gives me a piece of mind. A wonderful sitter and person!

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

Kim did a great job taking care of our cat for two weeks. I'm always nervous to leave our cat with someone new, but Kim was trustworthy, reliable, and provided nice updates for every drop-in visit. Our cat sometimes gets anxious when we're away, but I was so pleased to find that she seemed very happy when we got home. I did not see any signs of anxiety, so Kim must have made her feel very comfortable! I would definitely recommend Kim to anyone else looking for a pet sitter!

Confirmed availability: Memorial Day Weekend
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
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 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: 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.

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Sitter Profile Image: Azaria O.
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Sitter Profile Image: Azaria O.
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9. 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

Azaria was very flexible and understanding of our last minute schedule changes. She updated us with pictures and took great care of our cats. Highly recommended!

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
1.1 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jennifer L.
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Sitter Profile Image: Jennifer L.
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11. 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

Thank you for taking such good care of our fur baby! This was our first time using Rover and traveling away from our pup after recently moving. Jennifer was an excellent sitter with great communication and great patience with our sensitive pup. Highly recommend!

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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
1.7 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!

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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
2.7 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!

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Sitter Profile Image: Cleda W.
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Sitter Profile Image: Cleda W.
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14. Cleda W.

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

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: 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
5 repeat clients
from
$22
per visit

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: Samantha K.
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Sitter Profile Image: Samantha K.
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16. 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dietrich G.
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Sitter Profile Image: Dietrich G.
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17. Dietrich G.

Dietrich is a dog's delight
Walnut Grove, MADISON, WI, 53717
0.6 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!

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Sitter Profile Image: Bailee B.
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Sitter Profile Image: Bailee B.
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18. Bailee B.

Time with pets is time well spent.
Sauk Creek, Madison, WI, 53717
0.8 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.

Sitter Profile Image: Anna N.
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Sitter Profile Image: Anna N.
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19. Anna N.

Professional student who loves dogs
Madison, WI, 53705
1.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$15
per visit

Anna is the best choice to care for your dog. She kept us updated on our puppy, did fun activities with our puppy, and even had little treats with him. You can tell that she is a huge dog-lover and will go above and beyond for your dog’s care!

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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
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
16 repeat clients
from
$25
per visit

Would absolutely recommend Alisyn!! She has been wonderful with our older dog, Indy, over the last year. When we added a second dog (a young rescue with heartworm disease), I knew I could trust Alisyn to take great care of Eeva and keep her safe during treatment, too. We are so grateful to have such a dependable, experienced, and compassionate person watching and walking our pups!

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Dog lovers in Woodlands, Madison, WI love pet sitters on Rover.com. Over 423 pet owners have reviewed pet sitters on Rover in Madison, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable pet sitting in Madison can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

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 Woodlands 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 Woodlands, 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 Woodlands pet sitters and avoid the kennel.

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