Pet Sitting & Drop Ins in Cherokee Garden, Madison, WI

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

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Sitter Profile Image: Jen D.
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Sitter Profile Image: Jen D.
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1. Jen D.

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

I will have to book Jen again as my dog will sure miss her! She was wonderful and so easy to work with. Momo will definitely be sad she won’t see you as often. Thank you for all you do!

Availability updated today
Sitter Profile Image: Alanna S.
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Sitter Profile Image: Alanna S.
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2. Alanna S.

Star Sitter
YOUR pet is the highlight of MY day
DeForest, WI, 53532
6.0 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
33 reviews
10 repeat clients
Profile image

I booked with Alanna again for a last-minute holiday trip, and once again, she went above and beyond for my babies. Her extra care and love meant the world to me, especially since I couldn’t be with them for Christmas. I’m so grateful for the kindness and attention she showed to my crew—it truly gave me peace of mind!

Availability updated 3 days ago
Sitter Profile Image: Laura S.
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Sitter Profile Image: Laura S.
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3. Laura S.

Star Sitter
My care is built around your pet.
Rolling Meadows, Madison, WI, 53714
4.9 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$18
per visit
5 out of 5.0 stars
13 reviews
4 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
Sitter Profile Image: Megan B.
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Sitter Profile Image: Megan B.
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4. Megan B.

Owner Away? I’ll Sit, Stay and Walk
Sun Prairie, WI, 53590
4.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$18
per visit
5 out of 5.0 stars
12 reviews
4 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 6 days ago
Sitter Profile Image: Maggie P.
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Sitter Profile Image: Maggie P.
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5. 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
46 reviews
12 repeat clients
Profile image

Maggie dropped by to meet the week before so we could go over expectations both of us had and to meet my girls. From what I could see when I returned, things were left where they needed to be, and more importantly, the girls were fed and happy. The pictures she sent were a fun way to know the girls were being looked after! She was flexible as I made changes, since my original booking accounted for morning visits instead of afternoon visits and I needed to cancel a couple of days' visits. Thank you, Maggie!

Availability updated 2 days ago
Sitter Profile Image: Megan T.
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Sitter Profile Image: Megan T.
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6. Megan T.

Star Sitter
I love all animals
Eken Park, Madison, WI, 53704
3.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$16
per visit
5 out of 5.0 stars
18 reviews
4 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
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Steve J.
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Sitter Profile Image: Steve J.
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7. Steve J.

Wholesome wags and pawsitive purrs
Monona, WI, 53714
4.9 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
2 reviews
2 repeat clients
Profile image

Steve did a wonderful job of checking in on my fuzzball and giving me updates. Highly recommended!

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Taryn E.
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Sitter Profile Image: Taryn E.
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8. Taryn E.

Rover 101
Star Sitter
Fun animal lover!
Windsor, WI, 53598
4.9 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
19 reviews
8 repeat clients
Profile image

Taryn was excellent. It was our first time using Rover for drop-in visits. Our cats loved Taryn and she took great care of them. She was a great communicator and went above and beyond. We will definitely use Rover again because of our wonderful experience with Taryn.

Availability updated 27 days ago
Sitter Profile Image: Anne S.
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Sitter Profile Image: Anne S.
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9. Anne S.

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

Anne did a fabulous job!! Her sweet, calm energy put my anxious cats at ease. She did wonderful with my finicky instructions, sent helpful updates with pictures, and took great care with my girls. I was able to relax and enjoy my vacation knowing they were in good hands.

Availability updated 7 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Katie T.
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Sitter Profile Image: Katie T.
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10. Katie T.

Star Sitter
ACTIVE, FLEXABLE, DOG LOVER
Marquette, Madison, WI, 53703
4.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 4.9 stars
25 reviews
3 repeat clients
Profile image

Katie was very communicative with us and was great with Iggy, even during his first meeting hyperactive moments! Would definitely recommend to others and would hire again!

Availability updated yesterday
Sitter Profile Image: Christine W.
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Sitter Profile Image: Christine W.
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11. Christine W.

Loving Care for Pets Big & Small
Emerson East, Madison, WI, 53704
3.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$13
per visit
2 reviews

Your pet will truly be in the best of care with Christine. You could not ask for a better person who knows so much about pet care! She has personally loved such.a wide variety of pets with such compassion, that whether you have a dog, cat, beta fish or fancy rats, she will do everything she possibly can to insure they are well cared for. I lived with Christine for several years, and during the time we were together, I saw how much care she put in to each and every pet member of our household, whether or not she was the "owner" of the pet or if their care was her "responsibility." She even has vet assistance and grooming experience so you know your pet is in good hands! Having lived with Christine and seen her dedication to responsible pet ownership day in and day out, I know from experience that you can trust that she will give extra consideration and genuine care to your pets.

Availability updated 5 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Annmarie S.
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Sitter Profile Image: Annmarie S.
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12. Annmarie S.

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

Communication with Annmarie was easy and clear and her updates were very appreciated. My cat and dog clearly had a nice time with her. Would definitely book with her again.

Availability updated 13 days ago
Sitter Profile Image: Jennifer K.
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Sitter Profile Image: Jennifer K.
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13. Jennifer K.

Purr-fect Peace & Tail-Wagging Joy
Madison, WI, 53704
1.1 mi. away
Drop-In Visits, Dog Walking
from
$13
per visit
5 years of experience

About: With 5 years of experience caring for dogs, through fostering and those of friends and family, I’ve gained a deep understanding of their unique personalities and needs. I respect every dog’s individuality and adapt my care to provide just the right balance of attention and activity. Whether your pup enjoys leisurely companionship and a calm presence or thrives on interactive play, exercise, and affection, I’m here to ensure they feel safe, happy, and fulfilled. My goal is to meet every dog where they are, providing thoughtful, loving care tailored to their needs. Working from home allows me to offer flexible scheduling for pet care. I can easily adapt to your needs, ensuring your pets receive timely and attentive care I prioritize understanding each pet's unique needs and preferences, whether at my home or yours. I adapt my care style to provide a safe, nurturing, and tailored environment for every furry friend

Availability updated 2 days ago
Sitter Profile Image: Ryan A.
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Sitter Profile Image: Ryan A.
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14. Ryan A.

Stay at home dog dad of two
Sherman, Madison, WI, 53704
2.2 mi. away
Drop-In Visits, Dog Walking
from
$19
per visit
5 out of 5.0 stars
7 reviews
2 repeat clients
Profile image

Ryan was very kind and prompt. He took time to to set up a meet and greet prior to his first visit. We will definitely have him again in the future!

Availability updated 57 days ago
Sitter Profile Image: Salem E.
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Sitter Profile Image: Salem E.
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15. Salem E.

I'm Salem, the gecko dad!
Sherman Village, Madison, WI, 53704
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per visit
5 out of 4.7 stars
28 reviews
8 repeat clients
Profile image

Salem did a great job with Misty and Phoebe. They were totally relaxed and happy when I arrived home. I appreciated Salem staying alittle longer on one of the days. Will definitely have her again.!

Availability updated 4 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Kagen & Matthew D.
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Sitter Profile Image: Kagen & Matthew D.
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16. Kagen & Matthew D.

Rover 101
Artist & Animal Lover You Can Trust
Sherman, Madison, WI, 53704
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 4.9 stars
66 reviews
31 repeat clients
Profile image

Kagen was prompt was so kind with Luna. Kagen made sure she had dinner and a nice break in the evening. Luna and I are looking forward to Kagen's future visits!

Availability updated 51 days ago
Sitter Profile Image: Sarah W.
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Sitter Profile Image: Sarah W.
Verified Enhanced Background Check

17. Sarah W.

Star Sitter
Pet lover with vet assistant exp.
Madison, WI, 53704
1.0 mi. away
Drop-In Visits, Dog Walking
from
$30
per visit
5 out of 5.0 stars
38 reviews
12 repeat clients
Profile image

Sarah took such great care of Pita! We appreciated the cute photos and pet POV updates that let us know how much Pita was loving Sarah’s visits. I would 100% recommend Sarah for any pet care needs!

Availability updated 16 days ago
Sitter Profile Image: Kaitlyn L.
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Sitter Profile Image: Kaitlyn L.
Verified Enhanced Background Check

18. Kaitlyn L.

Caring and trust worthy sitter :)
Whitetail Ridge, Madison, WI, 53704
0.6 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
7 reviews
1 repeat client
Profile image

Kaitlyn fed and visited with our dog Meg this past weekend. She took lots of pictures and was great about communicating with me. I will definitely be using her services again in the future!!

Availability updated yesterday
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Lauren K.
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Sitter Profile Image: Lauren K.
Verified Background Check

19. Lauren K.

Experience training dogs
Sherman Village, Madison, WI, 53704
0.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per visit
5 out of 5.0 stars
12 reviews
3 repeat clients

Lauren is fantastic with our dogs. When she dog sits for us, she is ensures to keep the dogs active and pampered throughout the day. She is consistently fun and caring and our dogs love spending time with her. She’s also helped us with a bit of training and advice on how to train good behaviors in and bad behaviors out.

Availability updated over 1 year ago
Sitter Profile Image: Amy Lynn R.
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Sitter Profile Image: Amy Lynn R.
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20. Amy Lynn R.

Rover 101
Happy Dog Boarding & Daycare, LLC
Whitetail Ridge, Madison, WI, 53704
0.7 mi. away
Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 5.0 stars
76 reviews
34 repeat clients
Profile image

We had Amy stop by to let our dogs out while we were at a wedding. They had only met her once before and took to her right away when she stopped by for a second pre-visit. Everything went great! The rover card was great and we really appreciated seeing some pictures (the dogs were relaxed and happy). Can't wait to use Amy again!

Availability updated 23 days ago

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