Pet Sitting & Drop Ins in Cherokee Park, 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: Brooke D.
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Sitter Profile Image: Brooke D.
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1. Brooke D.

Does your dog love walks? So do I!
High Crossing, Madison, WI, 53718
4.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
459 reviews
84 repeat clients
Profile image

Brooke was amazing!!! She sent GREAT pictures every time she checked in, was extremely neat and tidy, and was able to give my cat the pill he needed. That was the best feeling being away from home - known my animals were 100% taken care of. I will rebook her in a heartbeat!

Availability updated yesterday
Sitter Profile Image: Maggie P.
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Sitter Profile Image: Maggie P.
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2. Maggie P.

Young professional who loves pets!
Madison, WI, 53703
4.9 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5.0 out of 5 stars
35 reviews
8 repeat clients
Profile image

Maggie went above and beyond - including braving a winter snowstorm - to make sure our cat was well cared for while we were out of town. Couldn’t recommend more highly!

Availability updated 3 days ago
Sitter Profile Image: Jen D.
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Sitter Profile Image: Jen D.
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3. Jen D.

Attentive and Fun Dog Mom
Berkley Oaks, Madison, WI, 53704
1.5 mi. away
Drop-In Visits, Dog Walking
from
$21
per visit
5.0 out of 5 stars
27 reviews
8 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
Sitter Profile Image: Alexandria P.
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Sitter Profile Image: Alexandria P.
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4. Alexandria P.

G.O.A.T. pet-sitter!
Regent, Madison, WI, 53726
6.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
15 reviews
3 repeat clients
Profile image

Alexandria was amazing she went above and beyond for our family while out of town. My dog Indy looks forward to her visits and she took care of my hens too. Amazing.

Availability updated yesterday
Sitter Profile Image: Alana L.
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Sitter Profile Image: Alana L.
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5. Alana L.

Caring and detailed pet lover
Marquette, Madison, WI, 53704
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$17
per visit
5.0 out of 5 stars
29 reviews
8 repeat clients
Profile image

Radar was super comfortable with Alana from the very start, which was unusual and reassuring. Alana took great care of her and shared thorough reports and sweet photos. Much appreciated!

Availability updated yesterday
Sitter Profile Image: Alanna S.
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Sitter Profile Image: Alanna S.
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6. Alanna S.

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

Alanna was amazing! She sent super detailed Rover Cards, took a ton of pictures, and overall made us feel really comfortable that we had left our kitties in such good hands. We would totally book Alanna again and would recommend her to others. Thanks, Alanna!

Availability updated yesterday
Sitter Profile Image: Taelyn C.
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Sitter Profile Image: Taelyn C.
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7. Taelyn C.

Owners away? I will walk and play!
Madison, WI, 53703
4.0 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5.0 out of 5 stars
18 reviews
6 repeat clients
Profile image

Taelyn was an excellent pet sitter for our cat. She was extremely responsive, attentive to details, and she cared for Zephyr as if she was family. I loved the photos she sent- Zephyr looked so happy and she normally doesn't like strangers very much. I would definitely book with Taelyn again.

Availability updated 2 days ago
Sitter Profile Image: Toni S.
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Sitter Profile Image: Toni S.
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8. Toni S.

Love spending free time with pets
DeForest, WI, 53532
5.2 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$12
per visit
5.0 out of 5 stars
43 reviews
18 repeat clients
Profile image

Toni went above and beyond! Not only did she take superior care of our little cavapoo, Bailey, she brought our garbage cans in from the curb and offered to check in on Bailey one more time if we were running late. Excellent care and service!!

Availability updated 3 days ago
Sitter Profile Image: Anne S.
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Sitter Profile Image: Anne S.
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9. Anne S.

I will love your pet like my own!
Madison, WI, 53704
1.2 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$18
per visit
5.0 out of 5 stars
9 reviews
1 repeat client

Allow me to introduce my remarkable friend, Anne! She’s not only kind, caring, reliable and responsible but also a true animal enthusiast. She loves animals and cares for every furry companion she meets. Whether it’s a playful pup or a gentle feline, she showers them with love, ensuring their well-being and happiness. 🐶🐱❤️ Trust Anne to take care of any of your animal's needs and they will truly be in great hands!

Availability updated 2 days ago
Sitter Profile Image: Anna N.
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Sitter Profile Image: Anna N.
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10. Anna N.

I will love your pets like my own!
Madison, WI, 53704
1.2 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
19 reviews
6 repeat clients
Profile image

Anna watched our cats while we were away for a week. She was amazing and very thoughtful! She even enticed my very shy cat out for some treats and pets.

Availability updated today
Sitter Profile Image: Megan W.
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Sitter Profile Image: Megan W.
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11. Megan W.

Your Best Friend’s New Best Friend!
Sun Prairie, WI, 53590
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$27
per visit
5.0 out of 5 stars
122 reviews
37 repeat clients
Profile image

First time customer. Megan took care of Oliver and Peach well and sent lots of updates while we are away for our vacation. Our cats were in good shape as we are back.

Availability updated yesterday
Sitter Profile Image: Amanda L.
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Sitter Profile Image: Amanda L.
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12. Amanda L.

Looking for ❤️ in the right place
Madison, WI, 53718
4.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$13
per visit
5.0 out of 5 stars
31 reviews
11 repeat clients
Profile image

Amanda is Awesome! She is an excellent communicator and took wonderful care of my dogs. I highly recommend!!!

Availability updated 7 days ago
Sitter Profile Image: Sarah W.
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Sitter Profile Image: Sarah W.
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13. Sarah W.

Pet lover with vet assistant exp.
Madison, WI, 53704
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$26
per visit
5.0 out of 5 stars
18 reviews
4 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 today
Sitter Profile Image: Megan T.
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Sitter Profile Image: Megan T.
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14. Megan T.

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

Megan was great at communicating and was attentive to all our animals. Her updates were detailed and were mindful of the various issues our elderly cats had, reporting on them and giving me enough information to give guidance on their meds. She was reliable and I felt like our pets were in good hands during our trip.

Availability updated today
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
$15
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients

Salem would be a great fit for anyone looking to find a caring and flexible person to look after their pets. With a slew of geckos of their own and two family dogs, they have experience with furry and not-so-furry friends! Their genuine passion for animals shines through in every interaction, making them a trustworthy and compassionate caretaker. I highly recommend Salem to anyone seeking top-notch care for their furry family members!

Availability updated 27 days ago
Sitter Profile Image: Henry M.
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Sitter Profile Image: Henry M.
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16. Henry M.

Ready to watch any furry friend!
Eken Park, Madison, WI, 53704
3.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$13
per visit
10 years of experience

About: I've taken care of and watched dogs since I was a teenager. My parents have had Saint Bernard Great Dane mixed breed dogs so I have a lot of experience dealing with giant breed dogs. When my parents current dog was a puppy, I had a lot of one on one time taking care of her especially when she was a puppy and first coming home because my parents were working and I was on summer break, this has given me an intimate understanding of the needs of puppies and how to take care of them. My parents have also always had cats and they don't always get along with the dog which has given me a lot of experience managing animals in conflict while working to make them more comfortable and get along more. I've also done a lot of work watching my partner's family dog which has given me a lot of experience dealing with dog reactivity and aggression and learning how to calm dogs down. I'm currently in between jobs so I have all of the time in the world to watch your pet! Amy schedule is incredibly flexible and I can be available for drop in visits, sitting, and other services in general and especially on weekends I can easily crate a dog if needed and I also love getting to lay on the couch or in bed with a puppy if they're allowed. I do have two cats but they can be kept in a bedroom and not interact with a dog if they are not cat friendly. If they are cat friendly, my cats love to play and would be really interested in meeting and cuddling with more dogs!

Availability updated 6 days ago
Sitter Profile Image: Rachel R.
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Sitter Profile Image: Rachel R.
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17. Rachel R.

Excited to meet your furry friend!
Windsor, WI, 53598
3.5 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5.0 out of 5 stars
12 reviews
6 repeat clients
Profile image

Rachel has been helping us with cat visits while we vacation 2x per year. She is so easy to work with and is very responsive to messages. We always come home to clean litter boxes, full water dishes, and happy kitties. I would recommend Rachel for your pet care needs!

Availability updated over 1 year ago
Sitter Profile Image: Lindsey P.
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Sitter Profile Image: Lindsey P.
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18. Lindsey P.

Experienced Fur Baby Caretaker
Madison, WI, 53704
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5.0 out of 5 stars
5 reviews
3 repeat clients
Profile image

Good communication. Treated my cat well. Would book again.

Availability updated 10 days ago
Sitter Profile Image: Mckenzie K.
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Sitter Profile Image: Mckenzie K.
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19. Mckenzie K.

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

Mckenzie was great! She was incredibly professional, brought a notebook to our walk through to make sure she had the key details and sent so many wonderful photos and updates about our cats while we were away. She went above and beyond by tidying up on the last visit (emptying the litter genie and taking out the garbage). The only sitter that’s ever done that for us! Unnecessary but oh so lovely to come home to. Our cats were in great hands and we will certainly request McKenzie again in the future.

Availability updated 26 days ago
Sitter Profile Image: Nick K.
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Sitter Profile Image: Nick K.
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20. Nick K.

Rover 101
Big Fenced yard, Dog Vacation spot!
Madison, WI, 53704
0.9 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$25
per visit
5.0 out of 5 stars
88 reviews
29 repeat clients

Nick has been a friend of mine for over three years now, and I know he is an awesome and caring person. He and his family have more animals than I would thing was possible including two dogs. I've always known him to love animals and take good care of them.

Availability updated 45 days ago

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Drop-In Visits