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
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Sitter Profile Image: Melinda N.
Verified Enhanced Background Check
Sitter Profile Image: Melinda N.
Verified Enhanced Background Check

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!

Sitter Profile Image: Seán & Leticia W.
Verified Enhanced Background Check
Sitter Profile Image: Seán & Leticia W.
Verified Enhanced Background Check

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
38 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.
Verified Background Check
Sitter Profile Image: Maiya W.
Verified Background Check

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
75 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.
Verified Enhanced Background Check
Sitter Profile Image: Ann V.
Verified Enhanced Background Check

4. Ann V.

Animal Lover and Law Student
Madison, WI, 53711
2.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
28 reviews
9 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: Keezieng V.
Verified Enhanced Background Check
Sitter Profile Image: Keezieng V.
Verified Enhanced Background Check

5. Keezieng V.

A dog person through & through
Arbor Hills, Madison, WI, 53713
4.5 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
43 reviews
19 repeat clients
from
$19
per visit

Keezieng's assistance was a lifesaver this holiday season. His politeness and kindness when meeting us and our cat Olivia was reassuring and he did a great job of updating us during his visits while we were away. We’re so grateful for the excellent care provided!

Sitter Profile Image: Lydia S.
Verified Background Check
Sitter Profile Image: Lydia S.
Verified Background Check

6. 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
38 reviews
15 repeat clients
from
$19
per visit

Lydia was great. Her communication with us while we were out of town was awesome. She was able to provide insulin injections without any problem. We would highly recommend her.

Sitter Profile Image: Dietrich G.
Verified Enhanced Background Check
Sitter Profile Image: Dietrich G.
Verified Enhanced Background Check

7. 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
17 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: Jennifer L.
Verified Background Check
Sitter Profile Image: Jennifer L.
Verified Background Check

8. 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
279 reviews
102 repeat clients
from
$22
per visit

Jennifer always does a wonderful job with our cat Percy! You can count on her to go the extra mile with your pet. She is incredibly easy to work with and will put you at ease right away. I would highly recommend her to anyone.

Sitter Profile Image: Allegra R.
Verified Enhanced Background Check
Sitter Profile Image: Allegra R.
Verified Enhanced Background Check

9. 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!

Sitter Profile Image: Cleda W.
Verified Background Check
Sitter Profile Image: Cleda W.
Verified Background Check

10. 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 so considerate and thoughtful and accommodating! The rover cards I received were full of pictures and fun details about her visit with James and Miles, two tricky shibas. She made sure they were well-cared for and I would 100% book with Cleda in the future. She is super reliable and really shows love and affection for our pets.

Sitter Profile Image: Whitney H.
Verified Background Check
Sitter Profile Image: Whitney H.
Verified Background Check

11. Whitney H.

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

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 earlier in the week. Needless to say, I was nervous to leave him. But Whitney was so responsive to all of my concerns and requests, and took really good care of him. Luckily there were no issues, but Whitney’s notes and care really helped put all my concerns at ease. Will definitely be requesting her services again!

Sitter Profile Image: Claire D.
Verified Enhanced Background Check
Sitter Profile Image: Claire D.
Verified Enhanced Background Check

12. Claire D.

Rover 101
Creature & Critter 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!

Sitter Profile Image: Kim M.
Verified Background Check
Sitter Profile Image: Kim M.
Verified Background Check

13. 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 was so easy to work with - she responds to messages very quickly, sent written and picture updates, and had a simple set-up for key drop off and pick up. I could tell my cat was very well cared for while I was gone!

Sitter Profile Image: Sara J.
Verified Enhanced Background Check
Sitter Profile Image: Sara J.
Verified Enhanced Background Check

14. 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.

Sitter Profile Image: Samantha K.
Verified Background Check
Sitter Profile Image: Samantha K.
Verified Background Check

15. 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: Bailee B.
Verified Enhanced Background Check
Sitter Profile Image: Bailee B.
Verified Enhanced Background Check

16. 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
7 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.
Verified Enhanced Background Check
Sitter Profile Image: Anna N.
Verified Enhanced Background Check

17. 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 such a wonderful person and especially a great dog lover and caregiver! We were roommates before, and she shared the responsibility of caring for my dog Cereal (she totally didn't need to)! She took Cereal on lakeside walks and to fenced areas to let Cereal have fun frequently. She paid careful attention to what happened to Cereal and was able to notice something abnormal. Anna was also immaculate with Cereal to wash her feet when she stepped on something gross and clean after when Cereal had an accident at home. Highly recommended to people who want their dogs to be taken seriously with love!!

Sitter Profile Image: Brooke S.
Verified Enhanced Background Check
Sitter Profile Image: Brooke S.
Verified Enhanced Background Check

18. Brooke S.

Your local pet friend!
Spring Harbor, Madison, WI, 53705
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit

Brooke is the only sitter my cat has ever tolerated and (maybe) even enjoyed a little bit. :) Her calm presence and gentle demeanor are such gifts for our beloved pets, and I was grateful to have her as my sitter for the time that I did. Brooke will give you peace of mind (and lots of fun pictures) while visiting your much loved furry friends. My apt always looked better than when I left it, and she cared for my cat as if he was her own.

Sitter Profile Image: Alisyn L.
Verified Enhanced Background Check
Sitter Profile Image: Alisyn L.
Verified Enhanced Background Check

19. 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

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!

Sitter Profile Image: Kally G.
Verified Enhanced Background Check
Sitter Profile Image: Kally G.
Verified Enhanced Background Check

20. Kally G.

Fun sitter with small service dog
Middleton, WI, 53562
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
59 reviews
15 repeat clients
from
$15
per visit

Kelly goes above and beyond when she checks in our pets. She obviously cares about what she does and we trust her to take care of our pup in our home. She even helped out with our chickens which I didn't even ask for. She's our go to when we get away from home for a weekend.

Search Map

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

Rover also offers other services in Woodlands:

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.

Drop-In Visits