Pet Sitting & Drop Ins in Woodlands, Madison, WI

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Sitter Profile Image: Maiya W.
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Sitter Profile Image: Maiya W.
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1. Maiya W.

Star Sitter
I'll love them like you love them!
Middleton, WI, 53562
1.7 mi. away
Drop-In Visits
from
$15
per visit
5 out of 5.0 stars
97 reviews
32 repeat clients
Profile image

Maiya did a great job with our cats; she sent pictures every day, the cats loved her, and the house was very clean when we came back from vacation. (She watered the plants and got the mail in as well).

Availability updated 15 days ago
Confirmed availability for 4th of July Weekend
Sitter Profile Image: Kim M.
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Sitter Profile Image: Kim M.
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2. Kim M.

Loving and experienced Dog Mom!
Middleton, WI, 53562
1.2 mi. away
Boarding, Drop-In Visits
from
$17
per visit
5 out of 5.0 stars
99 reviews
40 repeat clients
Profile image

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!

Availability updated 10 months ago
Confirmed availability for 4th of July Weekend
Sitter Profile Image: Natalie B.
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Sitter Profile Image: Natalie B.
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3. Natalie B.

Star Sitter
Stress-Free Trips Start with Me!
Madison, WI, 53715
4.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$20
per visit
5 out of 5.0 stars
127 reviews
41 repeat clients
Profile image

Natalie was wonderfully flexible in working around our busy schedules to coordinate a meet and greet and key drop-off for our 2-day booking. Our kitty Millie is not shy about expressing her opinions of other people, and she was warm toward Natalie right away. We came home to a clean litter box and a happy, chill cat! She even remembered me mention that Millie loves to sit outside and made time to take her out on the patio. Thanks, Natalie!

Availability updated 5 days ago
Sitter Profile Image: Ann V.
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Sitter Profile Image: Ann V.
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4. Ann V.

Star Sitter
Animal Lover and Law Student
Madison, WI, 53711
3.7 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
82 reviews
24 repeat clients
Profile image

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!

Availability updated yesterday
Sitter Profile Image: Anna O.
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Sitter Profile Image: Anna O.
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5. Anna O.

Star Sitter
Will treat your sweet pet as my own
Madison, WI, 53711
2.9 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
17 reviews
4 repeat clients
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Anna did a great job with our girls! We received photos and a quick update on how they were doing during her check in. Couldn't have asked for a better experience.

Availability updated 3 days ago
Sitter Profile Image: Laura D.
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Sitter Profile Image: Laura D.
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6. Laura D.

Star Sitter
Pet lover of both dogs and cats
Madison, WI, 53719
3.3 mi. away
Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
9 reviews
2 repeat clients
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Laura was great with our new puppy! She was easy to get in touch with on the app and was such a joy to work with. We definitely hope to use her services again in the future!

Availability updated 8 days ago
Sitter Profile Image: Krista C.
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Sitter Profile Image: Krista C.
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7. Krista C.

Star Sitter
I've never met a pet I didn't LOVE!
Verona, WI, 53593
3.7 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
90 reviews
21 repeat clients
Profile image

Krista was so wonderful with my Bailey girl. She was so thorough with making sure she knew what Bailey needed and I wanted for their time together. I had no worries with Krista taking care of my dog and will definitely have her back! She’s such a sweetheart with a kind soul and your pets will be drawn to her!

Availability updated 3 days ago
Confirmed availability for 4th of July Weekend
Sitter Profile Image: Annie J.
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Sitter Profile Image: Annie J.
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8. Annie J.

Rover 101
Star Sitter
Active & communicative pet lover!
Midvale Heights Community, Madison, WI, 53711
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
55 reviews
20 repeat clients
Profile image

I strongly recommend Annie! She is super easy to work with. Although we had a last minute appointment, Annie was very responsive and quickly arrange a meet and greet. She followed our instructions meticulously, provided super detailed descriptions of her activities with our cat, and sent a lot of lovely pictures, which was very assuring and substantially eased our anxiety away from our cat. Thank you, Annie!!

Availability updated 2 days ago
Sitter Profile Image: Lydia S.
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Sitter Profile Image: Lydia S.
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9. Lydia S.

Here to help with your schedule
Middleton, WI, 53562
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
119 reviews
38 repeat clients
Profile image

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.

Availability updated 12 days ago
Confirmed availability for 4th of July Weekend
Sitter Profile Image: Cleda W.
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Sitter Profile Image: Cleda W.
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10. Cleda W.

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

Always super reliable! We know we can count on Cleda to do great drop ins with our cats when out of town. Very communicative and goes beyond to make sure the cats are taken care of

Availability updated yesterday
Confirmed availability for 4th of July Weekend
Sitter Profile Image: Sarah S.
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Sitter Profile Image: Sarah S.
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11. Sarah S.

Star Sitter
Hoping I can meet your fur babies!
Sunset Village, Madison, WI, 53705
2.6 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
120 reviews
35 repeat clients
Profile image

Sarah was absolutely fantastic, 10/10! It was my first time using rover and she was super patient while explaining everything to me. She took the time to do a meet and greet and my cat (who is very skeptical of most and kinda cranky) warmed up to her immediately. While away, I got constant communication and photos. I can’t wait to use Sarah again next time I’m out of town - thank you!!!

Availability updated 5 days ago
Sitter Profile Image: Yvonne L.
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Sitter Profile Image: Yvonne L.
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12. Yvonne L.

Star Sitter
I take pet care very seriously!
Madison, WI, 53705
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
17 reviews
5 repeat clients
Profile image

Evee took excellent care of our kitties (and fish)! She sent daily communication and texted if she had any questions. We will definitely be asking her to pet sit for us again!

Availability updated 16 days ago
Sitter Profile Image: Julie A.
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Sitter Profile Image: Julie A.
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13. Julie A.

Star Sitter
Mature, skilled and flexible
Verona, WI, 53593
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$13
per visit
5 out of 5.0 stars
15 reviews
3 repeat clients
Profile image

Julie is awesome. She is kind and patient with senior dogs. She’s reliable and jumps in to assist in even if n situations where there is a short notice. Thank you Julie

Availability updated 5 days ago
Sitter Profile Image: Jennifer L.
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Sitter Profile Image: Jennifer L.
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14. Jennifer L.

Rover 101
Star Sitter
AVAILABLE THIS WEEKEND! TOP RATED!
Madison, WI, 53705
1.4 mi. away
Drop-In Visits, Dog Walking
from
$21
per visit
5 out of 5.0 stars
424 reviews
138 repeat clients
Profile image

Even when you have spare travel plans. Jennifer will definitely remember you. She’s awesome. She loves the animals and makes me feel 10x better about going somewhere when I need to. Thank you so much again Jennifer ! 🤗🤗🤗

Availability updated 3 days ago
Confirmed availability for 4th of July Weekend
Sitter Profile Image: Sidney R.
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Sitter Profile Image: Sidney R.
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15. Sidney R.

Star Sitter
They call me “The Pal Gal”!
Middleton, WI, 53562
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 4.9 stars
60 reviews
20 repeat clients
Profile image

Sidney was so professional work with, and we appreciated her responding to us so quickly when we needed help on short notice. Layla loved her! We will definitely use Sidney again.

Availability updated 4 days ago
Sitter Profile Image: Allegra R.
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Sitter Profile Image: Allegra R.
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16. Allegra R.

Rover 101
Star Sitter
Dog person for life.
Faircrest, Madison, WI, 53705
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 4.9 stars
75 reviews
34 repeat clients
Profile image

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!

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

I come from a family of dog lovers
Madison, WI, 53705
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
7 reviews
2 repeat clients
Profile image

Highly recommend Sabrina! She adapted to Chewbacca's needs and even introduced ways to get him to eat that I didn't even think about. Chewy's a stubborn, grumpy old poodle and he opened up to her!! Sabrina was easy to communicate with and sent plenty of updates to keep me in the loop. She went above and beyond with everything and treated Chewy like her own. I'll definitely choose her next time Chewy needs a sitter!

Availability updated 20 days ago
Sitter Profile Image: Anna H.
Verified Enhanced Background Check
Sitter Profile Image: Anna H.
Verified Enhanced Background Check

18. Anna H.

The best care for your best friend!
Middleton, WI, 53562
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
29 reviews
7 repeat clients
Profile image

Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!

Availability updated today
Sitter Profile Image: Samantha K.
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Sitter Profile Image: Samantha K.
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19. Samantha K.

Star Sitter
I’ll take good care of your buddies
Middleton, WI, 53562
1.8 mi. away
House Sitting, Drop-In Visits
from
$20
per visit
5 out of 4.9 stars
33 reviews
11 repeat clients
Profile image

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!

Availability updated 5 days ago
Sitter Profile Image: Hannah I.
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Sitter Profile Image: Hannah I.
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20. Hannah I.

Rover 101
Star Sitter
Dogs love to run and play with me!
Wexford, Madison, WI, 53717
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
100 reviews
32 repeat clients
Profile image

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)!

Availability updated yesterday

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