Pet Sitting & Drop Ins in Westchester Gardens, Madison, WI

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

Search

More resources

A focus on safety

Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check.Learn more about RoverProtect

Loving pet sitters in your neighborhood

Search Results

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

1. Jen D.

Star Sitter
Attentive and Fun Dog Mom
Berkley Oaks, Madison, WI, 53704
2.0 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
73 reviews
20 repeat clients
Profile image

Jen was very attentive with Iroh and made sure that he was well cared for in our absence. I would happily book her again and recommend her to any pet parent!

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Brianna M.
Verified Enhanced Background Check
Sitter Profile Image: Brianna M.
Verified Enhanced Background Check

2. Brianna M.

Star Sitter
Patience, affection, and play time!
Bluff Acres, Madison, WI, 53704
1.1 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per visit
5 out of 5.0 stars
15 reviews
5 repeat clients
Profile image

Brianna did an amazing job taking care of my cat Rhubarb! She is an experienced pet sitter/owner and was able to give Rhu her liquid medication. She was also super communicative and friendly; I really appreciated her report cards describing their time together, complete with lots of photos!

Availability updated 4 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Joan F.
Verified Background Check
Sitter Profile Image: Joan F.
Verified Background Check

3. Joan F.

Star Sitter
Your four-leggers home on the park
Eastmorland, Madison, WI, 53714
2.5 mi. away
Boarding, Drop-In Visits
from
$15
per visit
5 out of 5.0 stars
110 reviews
34 repeat clients
Profile image

Joan has been a sitter for us twice on very short notice and done a fabulous job! She takes great photos, super reliable and is very communicative in providing updates!

Availability updated today
Sitter Profile Image: Kathryn N.
Verified Enhanced Background Check
Sitter Profile Image: Kathryn N.
Verified Enhanced Background Check

4. Kathryn N.

Reliable Care When You're Not There
McClellan Park, Madison, WI, 53718
3.4 mi. away
Drop-In Visits, Dog Walking
from
$19
per visit
5 out of 5.0 stars
6 reviews
1 repeat client
Profile image

Kathryn is amazing. Extremely attentive to my baby’s needs and super flexible with our schedule. Her communication goes beyond expectation and has made our experience of rover great!

Availability updated 2 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Laura S.
Verified Enhanced Background Check
Sitter Profile Image: Laura S.
Verified Enhanced Background Check

5. Laura S.

Star Sitter
My care is built around your pet.
Rolling Meadows, Madison, WI, 53714
2.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$18
per visit
5 out of 5.0 stars
13 reviews
3 repeat clients

Laura truly cared for my two dogs like they were her own. She was very attentive to their individual needs and quirks and went out of her way to make them feel comfortable with her. My one dog, Freddie, is fearful of new people and was initially skeptical of Laura. By the end of the week, she was easily his favorite human! It is a huge relief knowing your critters are well taken care of and well loved when you're away. She sent us regular photos and updates and was wonderful all around. Highly recommend!

Availability updated 4 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Zay O.
Verified Enhanced Background Check
Sitter Profile Image: Zay O.
Verified Enhanced Background Check

6. Zay O.

Star Sitter
Bringing quality care to all floofs
Westchester Gardens, Madison, WI, 53702
0.5 mi. away
Drop-In Visits, Dog Walking
from
$22
per visit
5 out of 5.0 stars
12 reviews
2 repeat clients
Profile image

Zay was great with our dog Honey and also great at keeping in contact with us from beginning to end. As soon as she met our dog I could tell that she would have a great energy around her to help out while we were away. Would definitely ask for her to watch our dog while we are away again.

Availability updated 9 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Annmarie S.
Verified Enhanced Background Check
Sitter Profile Image: Annmarie S.
Verified Enhanced Background Check

7. Annmarie S.

Star Sitter
Gentle and Loving for All Animals
Emerson East, Madison, WI, 53704
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
13 reviews
2 repeat clients
Profile image

Annmarie was super responsive and able to help us last minute with some drop in visits during a day we had to work. She hung outside with our old man so that he could enjoy some sun. We are very thankful for her care!

Availability updated yesterday
Sitter Profile Image: Brittany S.
Verified Enhanced Background Check
Sitter Profile Image: Brittany S.
Verified Enhanced Background Check

8. Brittany S.

Star Sitter
Happy to check in!
Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53714
2.3 mi. away
Drop-In Visits, Dog Walking
from
$16
per visit
5 out of 5.0 stars
11 reviews
6 repeat clients
Profile image

Brittany was kind, friendly, and great at communicating. She paid attention to details and even offered to help with extras beyond the cats. I’d recommend her to anyone needing a reliable sitter.

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Megan B.
Verified Background Check
Sitter Profile Image: Megan B.
Verified Background Check

9. Megan B.

Owner Away? I’ll Sit, Stay and Walk
Sun Prairie, WI, 53590
3.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$15
per visit
5 out of 5.0 stars
10 reviews
3 repeat clients

Dependable dog walker who really understands animals and animal behavior. She has trained a Guiding Eyes Dog and has a degree in animal science. Plus she just loves loves loves dogs!

Availability updated 7 days ago
Sitter Profile Image: Mark L.
Verified Enhanced Background Check
Sitter Profile Image: Mark L.
Verified Enhanced Background Check

10. Mark L.

Star Sitter
Animal lover, biology author
McClellan Park, Madison, WI, 53718
3.7 mi. away
House Sitting, Drop-In Visits
from
$15
per visit
5 out of 4.9 stars
37 reviews
8 repeat clients
Profile image

Mark has come to let out dog out twice and has been great both times!! He communicates, sent photos and our doodle always have a great time with him!

Availability updated 35 days ago
Sitter Profile Image: Megan T.
Verified Enhanced Background Check
Sitter Profile Image: Megan T.
Verified Enhanced Background Check

11. Megan T.

I love all animals
Eken Park, Madison, WI, 53704
2.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$16
per visit
5 out of 5.0 stars
16 reviews
3 repeat clients
Profile image

Megan was so fantastic with my energetic, young kitty!! She was very communicative and flexible. Will be using her services again. Thanks Megan!!

Availability updated today
Sitter Profile Image: Jilly D.
Verified Enhanced Background Check
Sitter Profile Image: Jilly D.
Verified Enhanced Background Check

12. Jilly D.

Rain or Shine Dog Walking
Sun Prairie, WI, 53590
3.5 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
10 reviews
5 repeat clients
Profile image

Jilly is the best! She took care of our dogs while we were out of town for a long weekend. She came over to meet the dogs before the weekend and took notes on their routine and preferences. Throughout the weekend she provided updates and sent pictures. She loved our pups as if they were her own! Our younger dog loved that Jilly played ball with her out in the yard and played inside too. Our senior dog enjoyed the snuggling. Today Jilly came over to return our house key. The dogs were really excited to see her. Jilly took our pup outside and played ball with her for a bit. I will definitely hire Jilly again!

Availability updated 17 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Amanda K.
Verified Background Check
Sitter Profile Image: Amanda K.
Verified Background Check

13. Amanda K.

Star Sitter
Responsible, active, pet owner
Cottage Grove, WI, 53527
4.9 mi. away
Boarding, Drop-In Visits
from
$15
per visit
5 out of 5.0 stars
149 reviews
51 repeat clients
Profile image

Amanda is great with checking in on our cat while we're away! She goes above and beyond, and is someone I'd absolutely not hesitate to use in the future.

Availability updated 7 days ago
Sitter Profile Image: Jaimielyn B.
Verified Enhanced Background Check
Sitter Profile Image: Jaimielyn B.
Verified Enhanced Background Check

14. Jaimielyn B.

Here to relieve your worries
Heistand, Madison, WI, 53714
2.0 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
8 reviews
1 repeat client
Profile image

Jaimielyn was absolutely wonderful! I had her for a drop in for my puppy on a Saturday. She was communicative, easy to schedule with, and followed my instructions regarding feeding Cosette dinner and what she needed. I truly appreciated that she was reliable and great with my puppy. I would highly recommend Jaimielyn.

Availability updated 8 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Jessica G.
Verified Enhanced Background Check
Sitter Profile Image: Jessica G.
Verified Enhanced Background Check

15. Jessica G.

I’m here to help! 🐶 🐱
Madison, WI, 53704
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per visit
5 out of 5.0 stars
22 reviews
4 repeat clients
Profile image

Jess did great! Communication was very clear, easy, and open. She was attentive and patient with my dog and kept me informed. She’s awesome!

Availability updated 4 days ago
Sitter Profile Image: Maggie P.
Verified Enhanced Background Check
Sitter Profile Image: Maggie P.
Verified Enhanced Background Check

16. Maggie P.

Star Sitter
Young professional who loves pets!
Tenney-Lapham, Madison, WI, 53703
4.6 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
43 reviews
11 repeat clients
Profile image

Our first time having Maggie care for our cats went great! After spending a year and a half working hard to integrate our two cat household, this was our first time leaving them alone together for more than a day, and one of our kitties needs daily anxiety medication to keep the peace. We were gone for 5 days and when we came back everyone was happy, healthy and the house looked just as it did when we left it. Will definitely be using Maggie again in the future if our schedules align!

Availability updated 10 days ago
Sitter Profile Image: Anne S.
Verified Enhanced Background Check
Sitter Profile Image: Anne S.
Verified Enhanced Background Check

17. Anne S.

Star Sitter
I will love your pet like my own!
Madison, WI, 53704
3.3 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
16 reviews
3 repeat clients
Profile image

Anne was great! Kept me updated and sent pictures of the pups too!

Availability updated 7 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Brooke D.
Verified Enhanced Background Check
Sitter Profile Image: Brooke D.
Verified Enhanced Background Check

18. Brooke D.

Star Sitter
Does your dog love walks? So do I!
High Crossing, Madison, WI, 53718
1.9 mi. away
Drop-In Visits
from
$20
per visit
5 out of 5.0 stars
521 reviews
92 repeat clients
Profile image

Brooke was wonderful to have pet sit our cat Henny! She took such good care of him and sent lots of fun photos of playing with him, always sending a thoughtful note care of how they spent their time together. We are grateful to have had such a responsible and caring pet sitter!

Availability updated 47 days ago
Sitter Profile Image: Mckenzie K.
Verified Background Check
Sitter Profile Image: Mckenzie K.
Verified Background Check

19. Mckenzie K.

Need the puuur-fect sitter?
Madison, WI, 53704
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$19
per visit
5 out of 5.0 stars
16 reviews
6 repeat clients
Profile image

Mckenzie has been absolutely amazing with Gato & Abigail! She does check-ins three times a week and has been incredibly reliable and communicative every step of the way. I always get updates and pictures after every visit and it’s clear she genuinely cares about them. Having her checking on them puts our minds at ease. Highly recommend McKenzie to anyone looking for trustworthy and professional pet sitter.

Availability updated 19 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Meghan & Jacob D.
Verified Enhanced Background Check
Sitter Profile Image: Meghan & Jacob D.
Verified Enhanced Background Check

20. Meghan & Jacob D.

Star Sitter
We’ll treat your pet like our own!
McClellan Park, Madison, WI, 53718
3.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$15
per visit
5 out of 5.0 stars
65 reviews
23 repeat clients
Profile image

Meghan and Jacob were excellent sitters! We are very happy with their services. They took checked in on our two cats while we were out of town for two weeks. They were also kind enough to take care of our many houseplants. They also sent great little updates in their daily reports, along with excellent pictures of our little guys. We looked forward to their report card every morning. Highly recommend Meghan and Jacob!

Availability updated yesterday
Confirmed availability for Memorial Day Weekend

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Pet Sitting FAQs

Frequently asked questions about Rover

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge