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

Search Results

Calendar Recently Updated
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
2.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
37 reviews
12 repeat clients
from
$18
per visit

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.

Calendar Recently Updated
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
3.0 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.

Calendar Recently Updated
Sitter Profile Image: Ann V.
Verified Enhanced Background Check
Sitter Profile Image: Ann V.
Verified Enhanced Background Check

3. Ann V.

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

Ann was a lifesaver for my cat and I! I had a sitter cancel last minute and was able to book with Ann the day before my trip within 15 minutes of my request. Everyday she sent a long update and lots of photos. Highly recommend!

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

4. Kim M.

Loving and experienced Dog Mom!
Middleton, WI, 53562
2.6 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!

Calendar Recently Updated
Sitter Profile Image: Whitney H.
Verified Background Check
Sitter Profile Image: Whitney H.
Verified Background Check

5. Whitney H.

Rover 101
Reliable & caring dog/cat sitter!
Madison, WI, 53719
1.8 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!

Calendar Recently Updated
Sitter Profile Image: Allegra R.
Verified Enhanced Background Check
Sitter Profile Image: Allegra R.
Verified Enhanced Background Check

6. Allegra R.

Rover 101
Dog person for life.
Faircrest, Madison, WI, 53705
0.3 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.
Verified Background Check
Sitter Profile Image: Jennifer L.
Verified Background Check

7. Jennifer L.

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

Jennifer, Thank you so much for taking such good care of our Luna girl! We appreciate all of the wonderful pictures and updates that you provided us while you were watching her. This was our first time using Rover and not only did you you make it a great experience we are definitely going to use it in the future! Thank you for Luna’s goodie bag full of treats - those are her favorite ??

Calendar Recently Updated
Sitter Profile Image: Azaria O.
Verified Enhanced Background Check
Sitter Profile Image: Azaria O.
Verified Enhanced Background Check

8. Azaria O.

Pets don’t need us, we need them🙂
Verona, WI, 53593
3.2 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: Danielle M.
Verified Background Check
Sitter Profile Image: Danielle M.
Verified Background Check

9. 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 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!

Calendar Recently Updated
Sitter Profile Image: Corinne B.
Verified Enhanced Background Check
Sitter Profile Image: Corinne B.
Verified Enhanced Background Check

10. Corinne B.

Animal Lover
Madison, WI, 53719
1.4 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dietrich G.
Verified Enhanced Background Check
Sitter Profile Image: Dietrich G.
Verified Enhanced Background Check

11. Dietrich G.

Dietrich is a dog's delight
Walnut Grove, MADISON, WI, 53717
1.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
20 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!

Calendar Recently Updated
Sitter Profile Image: Jess B.
Verified Enhanced Background Check
Sitter Profile Image: Jess B.
Verified Enhanced Background Check

12. Jess B.

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

Jess has cared for our dog multiple times now and she always provides detailed notes so we know how our dog did while we were away and cares for our dog like her own!

Calendar Recently Updated
Sitter Profile Image: Valarie H.
Verified Enhanced Background Check
Sitter Profile Image: Valarie H.
Verified Enhanced Background Check

13. Valarie H.

Rover 101
Professional caregiver for your pet
Madison, WI, 53711
2.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
35 reviews
16 repeat clients
from
$20
per visit

Valarie was fantastic! She kept my kitties happy and healthy while I was away, and was so great about communicating with me. I look forward to her watching them again for my next trip!

Confirmed availability: Memorial Day Weekend
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
2.1 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: Ilise M.
Verified Enhanced Background Check
Sitter Profile Image: Ilise M.
Verified Enhanced Background Check

15. Ilise M.

Company for Your Furbaby!
Orchard Ridge Community, Madison, WI, 53711
1.6 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
37 reviews
10 repeat clients
from
$15
per visit

We have used Ilise several times for our cat. She is always reliable and communicates well. She couldn’t find our cat this visit and she ended up being in the garage! We were so glad to have her there and she knew that our cat should have greeted her. She saved the day!

Sitter Profile Image: Annalise C.
Verified Enhanced Background Check
Sitter Profile Image: Annalise C.
Verified Enhanced Background Check

16. Annalise C.

Just an all-round animal lover
Summit Woods, Madison, WI, 53711
2.3 mi. away
Drop-In Visits
5.0 out of 5 stars
2 reviews
3 repeat clients
from
$20
per visit

Annalise has done an amazing job with watching my cat when I’ve been on holiday. She goes above and beyond to keep her well cared for and loved on. I never have to worry when my cat is in her care.

Calendar Recently Updated
Sitter Profile Image: Hannah I.
Verified Background Check
Sitter Profile Image: Hannah I.
Verified Background Check

17. Hannah I.

Rover 101
Dogs love to run and play with me!
Madison, WI, 53719
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
82 reviews
27 repeat clients
from
$20
per visit

Hannah was awesome with our 11 yo rescue dog, very caring and spent quality time with her. Hannah is very responsible, showed up promptly, and Luna was very happy with her visit (we were too)!

Calendar Recently Updated
Sitter Profile Image: Cleda W.
Verified Background Check
Sitter Profile Image: Cleda W.
Verified Background Check

18. Cleda W.

Rover 101
Dogs & Cats LOVE me!
Madison, WI, 53705
1.4 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.

Calendar Recently Updated
Sitter Profile Image: Cindy D.
Verified Background Check
Sitter Profile Image: Cindy D.
Verified Background Check

19. 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 been dog-sitting my chihuahua for almost 12 years; I would never take my dog to another dog-sitter! Daisy is usually timid with new people, but she loves Cindy! Cindy is responsible, reliable, and provides a calm atmosphere for shy dogs to thrive in. She is also flexible and willing to follow any specific instructions you might have related to dog care. Highly recommended!

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

20. Hannah S.

Love to check on your fur babies!
Madison, WI, 53711
1.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
63 reviews
33 repeat clients
from
$20
per visit

This was the second time Hannah watched our cat for us, this time for a whole week. Our cat was well taken care of and I appreciated getting updates every visit. Hannah even noticed all our cat’s little habits, making me feel confident that she was being well cared for!

Search Map

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

Rover also offers other services in Oakwood Village:

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 423 owners have reviewed sitters in Oakwood Village, Madison, WI, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Oakwood Village, 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 Oakwood Village, Madison who can provide the care your pet needs, when they need it.

Drop-In Visits