House Sitting in Cherokee Park, Madison, WI

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Top rated Cherokee Park house sitters

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Sitter Profile Image: Tiana B.
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Tiana B.
Star Sitter
from
$50
per night
5 out of 5.0 stars
10 reviews
4 repeat clients
5 years of experience
DeForest, WI, 53532

Tiana was very dependable and took very good care of Hobbes

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Ray C.
Sitter Profile Image: Jolie Zevallos
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Jolie Zevallos
Star Sitter
from
$31
per night
5 out of 5.0 stars
11 reviews
5 repeat clients
8 years of experience
Madison, WI, 53715

Appreciate Jolie's diligent care for my buddies while I was away. Communicated well and tended to each of my dogs specific needs. Would be happy to have her back the next time I need a sitter.

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Erick S.
Sitter Profile Image: Katie T.
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Katie T.
Star Sitter
from
$60
per night
5 out of 4.9 stars
29 reviews
5 repeat clients
5 years of experience
Marquette, Madison, WI, 53703

Katie was wonderful with my dog and a great communicator. She sent lots of updates and I could tell she was taking great care of him. She went above and beyond! I would definitely utilize her again.

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Susana S.
Sitter Profile Image: Salem E.
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Salem E.
from
$35
per night
5 out of 4.7 stars
31 reviews
9 repeat clients
10 years of experience
Sherman Village, Madison, WI, 53704

Salem did a great job taking care of my two dogs. They stayed over at my house (cared for the dogs in my home while I was gone multiple days) and left things in good shape. They are super responsive, and sent me lots of photos and updates so I could see how everything was going. I would definitely recommend them!!

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Eve S.
Sitter Profile Image: Brenda S.
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Brenda S.
from
$40
per night
5 out of 5.0 stars
5 reviews
9 years of experience
Waunakee, WI, 53597

Brenda was amazing!!! She took great care of our house and our cats. Sent pictures and updates, and left the house cleaner than she found it. 😁 We needed last minute help, and she was so flexible and accommodating! I would not hesitate to hire her again!

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Alicia S.
Sitter Profile Image: Stephanie H.
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Stephanie H.
Star Sitter
from
$28
per night
5 out of 5.0 stars
13 reviews
2 repeat clients
23 years of experience
Eastmorland, Madison, WI, 53714

Stephanie took excellent care of our 4 year old poodle, bonding with him immediately and taking him on nice walks and keeping him happy while we were gone. She even brought her own long leash so he could run around at the park while she made sure he couldn’t take off. Very kind, conscientious sitter!

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Ruth C.
Sitter Profile Image: Natalee Y.
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Natalee Y.
from
$29
per night
5 out of 5.0 stars
7 reviews
2 repeat clients
11 years of experience
Madison, WI, 53706

Natalee was phenomenal with Remora! Consistent updates, cute pics of my cat, and very reliable with scheduling and coordination. Natalee took great notes to make sure Remora was cared for the best as could be. Thank you!!

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Elijah H.
Sitter Profile Image: Tina B.
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Tina B.
Star Sitter
from
$35
per night
5 out of 4.9 stars
66 reviews
21 repeat clients
38 years of experience
Windsor, WI, 53598

We had Tina meet our dogs to make sure she would want to do it. We have a needy Bulldog and a protective Mix. By the time Tina left our house, the dogs were great with her. She sent pictures and updates on the dogs daily and everything they were bothering her with, they bother our family with when were home. So we knew the dogs were comfortable. We will definitely seek out Tina in the future.

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Tanya O.
Sitter Profile Image: Samantha M.
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Samantha M.
from
$45
per night
10 years of experience
Madison, WI, 53704

Samantha is a very good worker. She is very responsable and she is always on time. She took care of Rokko very well and Rokko was very happy since the first moment. We appreciated her work very much.

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Sonia M.
Sitter Profile Image: Anna H.
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Anna H.
from
$65
per night
5 out of 5.0 stars
30 reviews
7 repeat clients
7 years of experience
Middleton, WI, 53562

Anna is a fantastic dog sitter who goes above and beyond for her clients. Before having Anna sit for us for the first time, she made the effort to come by and visit our pup. This was so important for there reasons: 1. Gave our pup the opportunity to become friends with Anna; 2. Allowed our dog to feel comfortable in her home with this new friend; and 3. Gave us the opportunity to show Anna where the important things for our dog are in the house. Anna is prompt and communicative. She gave us photo and text updates throughout her visit. She is clearly a kind and respectful person and dogs seem to love her immediately. I will most definitely reach out to Anna again for any dog sitting/house sitting occasions.

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Lesli M.
Sitter Profile Image: Sophie H.
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Sophie H.
from
$60
per night
5 out of 5.0 stars
58 reviews
16 repeat clients
3 years of experience
Regent, Madison, WI, 53726

Sophie was great. Communicative and left the house in great shape. She had to deal with my old pups stomach issues and I appreciated her willingness to help there. Would book again.

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Gopal S.
Sitter Profile Image: Vanessa U.
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Vanessa U.
from
$28
per night
5 out of 5.0 stars
3 reviews
4 years of experience
Sherman Terrace, Madison, WI, 53704

Vanessa was great! My dog loved her. Very communicative and goes the extra mile. I will definitely book her again.

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Gary C.
Sitter Profile Image: Nicholas & Lauren R.
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Nicholas & Lauren R.
from
$50
per night
5 out of 5.0 stars
4 reviews
38 years of experience
Madison, WI, 53704

Lauren and Nia were great with our pets and us! This was our first time using pet sitters and they really helped put us at ease through the process. With picture and video updates we knew our dogs and cats were having a good time and being well cared for. Highly recommend using them!

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Jessica F.
Sitter Profile Image: Jessica & Andrew B.
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Jessica & Andrew B.
from
$55
per night
5 out of 5.0 stars
18 reviews
5 repeat clients
15 years of experience
Waunakee, WI, 53597

Jessica was amazing from our first messages to her stay with my animals. Initially, I asked for references as I previously had a terrible experience on Rover and she was quick to provide me with the numbers of people she has sat for previously (with their permission). At our meet and greet my animals immediately took to her and her to them, and she was so comfortable even with their high excitement and noise levels. ;) During her stay with them, she kept in touch regularly with me and sent me so many pictures which I loved. I could tell she loved my animals which is always what you want from their caregiver. <3 My home was clean when I returned and, far more importantly, the animals had clearly been very loved on and wonderfully cared for! I recommend her so highly!! She is wonderful and my animals agree! :)

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Kelsey G.
Sitter Profile Image: Louisa S.
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Louisa S.
from
$45
per night
5 out of 5.0 stars
5 reviews
2 repeat clients
15 years of experience
Sun Prairie, WI, 53590

Louisa was excellent! She was so thorough in our meet and greet making sure she was aware of any and all needs Ollie might have. Ollie loved her right away which made me feel very comfortable. Louisa was great at communicating and sent pictures during the sit which I appreciated. Highly recommend her and will certainly have her care for Ollie in the future!

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Angi K.
Sitter Profile Image: Ashley H.
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Ashley H.
from
$28
per night
5 out of 5.0 stars
2 reviews
7 years of experience
Tenney-Lapham, Madison, WI, 53703

About: I’ve been taking care of animals all my life but have professionally done in the past 6 years! I love spending time around animals and I also stay hyper vigilant if there’s any issues going on! I am currently working in sales where I spend all day in Costco, so I'm looking for a way to get outside and make a new community of friends, and get some walk and play time in with a furry friend! Always more than happy to make time for your pet! I have a cat named Theo and he gets fed on a schedule three times a day, which seems to the perfect mix. I like to keep pets on a schedule and active so that they’re getting all the enrichment and care that they need! If there’s not a fenced in yard, I’m happy to go for a walk!

Sitter Profile Image: Joshua D.
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Joshua D.
from
$30
per night
5 out of 5.0 stars
6 reviews
2 repeat clients
10 years of experience
Hawthorne, Madison, WI, 53704

Josh was wonderful! Our dog can be wary of new people, but Josh took the time to get to know him and let Coqui warm up to him slowly. He was respectful of our property (left our house so clean), was highly responsive, and communicative. We will definitely hire Josh again!

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Jennifer A.
Sitter Profile Image: Karrie G.
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Karrie G.
from
$50
per night
10 years of experience
Waunakee, WI, 53597

About: I have experience caring for pets, having grown up with them, and I am available with a flexible schedule throughout the summer months. I would be happy to assist if needed. I am currently a teacher on summer break and have availability to assist with dog walking, provide daytime or evening companionship for pets, and house sit if needed! I genuinely enjoy spending time with animals—whether it's going for walks, playing fetch, or simply offering affection and companionship. My priority is always to ensure pets feel happy, safe, and well cared for.

Sitter Profile Image: Annmarie S.
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Annmarie S.
Star Sitter
from
$60
per night
5 out of 5.0 stars
17 reviews
6 repeat clients
15 years of experience
Emerson East, Madison, WI, 53704

Annemarie was a WONDERFUL dog sitter for my pup! She was so attentive and kept me informed the entire time, and Laika absolutely adored her. I will definitely be rebooking!

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Gabrielle C.
Sitter Profile Image: Samantha S.
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Samantha S.
from
$28
per night
31 years of experience
Madison, WI, 53704

About: I've had dogs and cats my whole life. I love a gentle giant as much as a little yapper. I have three cats, a bearded dragon, and a ball python myself. Dog walks are therapy, and I'm happy to dose meds, clean ears, or spend extra time throwing the ball (or snuggling with a senior buddy). I currently have wide-open availability and very flexible hours. I have organized sports I play in on Tuesday and Thursday evenings, which I simply work around for nighttime/evening potty breaks. I cannot offer in-home sitting at this time. My cats would be too disturbed and unhappy to have another fur baby in their shared space.

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Sitter Profile Image: Tiana B.
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Sitter Profile Image: Tiana B.
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Tiana B.
Star Sitter

Trustworthy & Reliable Dog Sitting
DeForest, WI, 53532
6.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5 out of 5.0 stars
10 reviews
4 repeat clients
Profile image

Tiana was very dependable and took very good care of Hobbes

Availability updated 3 days ago
Sitter Profile Image: Jolie Zevallos
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Sitter Profile Image: Jolie Zevallos
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Jolie Zevallos
Star Sitter

I love the fur babies so much
Madison, WI, 53715
6.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$31
per night
5 out of 5.0 stars
11 reviews
5 repeat clients
Profile image

Appreciate Jolie's diligent care for my buddies while I was away. Communicated well and tended to each of my dogs specific needs. Would be happy to have her back the next time I need a sitter.

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Katie T.
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Sitter Profile Image: Katie T.
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Katie T.
Star Sitter

ACTIVE, FLEXABLE, DOG LOVER
Marquette, Madison, WI, 53703
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 4.9 stars
29 reviews
5 repeat clients
Profile image

Katie was wonderful with my dog and a great communicator. She sent lots of updates and I could tell she was taking great care of him. She went above and beyond! I would definitely utilize her again.

Availability updated today
Sitter Profile Image: Salem E.
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Sitter Profile Image: Salem E.
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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
$35
per night
5 out of 4.7 stars
31 reviews
9 repeat clients
Profile image

Salem did a great job taking care of my two dogs. They stayed over at my house (cared for the dogs in my home while I was gone multiple days) and left things in good shape. They are super responsive, and sent me lots of photos and updates so I could see how everything was going. I would definitely recommend them!!

Availability updated yesterday
Sitter Profile Image: Brenda S.
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Sitter Profile Image: Brenda S.
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Brenda S.

Longtime pet sitter, new to Rover
Waunakee, WI, 53597
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
5 reviews
Profile image

Brenda was amazing!!! She took great care of our house and our cats. Sent pictures and updates, and left the house cleaner than she found it. 😁 We needed last minute help, and she was so flexible and accommodating! I would not hesitate to hire her again!

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Stephanie H.
Verified Enhanced Background Check
Sitter Profile Image: Stephanie H.
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Stephanie H.
Star Sitter

Dog lover pet spoiler
Eastmorland, Madison, WI, 53714
4.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
5 out of 5.0 stars
13 reviews
2 repeat clients
Profile image

Stephanie took excellent care of our 4 year old poodle, bonding with him immediately and taking him on nice walks and keeping him happy while we were gone. She even brought her own long leash so he could run around at the park while she made sure he couldn’t take off. Very kind, conscientious sitter!

Availability updated 2 days ago
Sitter Profile Image: Natalee Y.
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Sitter Profile Image: Natalee Y.
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Natalee Y.

Reliable Pet Care with Pride! 🐾🌈
Madison, WI, 53706
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$29
per night
5 out of 5.0 stars
7 reviews
2 repeat clients
Profile image

Natalee was phenomenal with Remora! Consistent updates, cute pics of my cat, and very reliable with scheduling and coordination. Natalee took great notes to make sure Remora was cared for the best as could be. Thank you!!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Tina B.
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Sitter Profile Image: Tina B.
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Tina B.
Star Sitter

Animal lover doing what I enjoy
Windsor, WI, 53598
4.7 mi. away
House Sitting, Drop-In Visits
from
$35
per night
5 out of 4.9 stars
66 reviews
21 repeat clients
Profile image

We had Tina meet our dogs to make sure she would want to do it. We have a needy Bulldog and a protective Mix. By the time Tina left our house, the dogs were great with her. She sent pictures and updates on the dogs daily and everything they were bothering her with, they bother our family with when were home. So we knew the dogs were comfortable. We will definitely seek out Tina in the future.

Availability updated 8 days ago
Sitter Profile Image: Samantha M.
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Sitter Profile Image: Samantha M.
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Samantha M.

College Student, Flexible, Reliable
Madison, WI, 53704
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
4 reviews
Profile image

Samantha is a very good worker. She is very responsable and she is always on time. She took care of Rokko very well and Rokko was very happy since the first moment. We appreciated her work very much.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Anna H.
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Sitter Profile Image: Anna H.
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Anna H.

The best care for your best friend!
Middleton, WI, 53562
7.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
30 reviews
7 repeat clients
Profile image

Anna is a fantastic dog sitter who goes above and beyond for her clients. Before having Anna sit for us for the first time, she made the effort to come by and visit our pup. This was so important for there reasons: 1. Gave our pup the opportunity to become friends with Anna; 2. Allowed our dog to feel comfortable in her home with this new friend; and 3. Gave us the opportunity to show Anna where the important things for our dog are in the house. Anna is prompt and communicative. She gave us photo and text updates throughout her visit. She is clearly a kind and respectful person and dogs seem to love her immediately. I will most definitely reach out to Anna again for any dog sitting/house sitting occasions.

Availability updated 2 days ago
Sitter Profile Image: Sophie H.
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Sitter Profile Image: Sophie H.
Verified Enhanced Background Check

Sophie H.

I would love to love your pets!
Regent, Madison, WI, 53726
6.2 mi. away
House Sitting
from
$60
per night
5 out of 5.0 stars
58 reviews
16 repeat clients
Profile image

Sophie was great. Communicative and left the house in great shape. She had to deal with my old pups stomach issues and I appreciated her willingness to help there. Would book again.

Availability updated today
Sitter Profile Image: Vanessa U.
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Sitter Profile Image: Vanessa U.
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Vanessa U.

Just call me Meowy Poppins! 🐾
Sherman Terrace, Madison, WI, 53704
4.0 mi. away
House Sitting, Drop-In Visits
from
$28
per night
5 out of 5.0 stars
3 reviews
Profile image

Vanessa was great! My dog loved her. Very communicative and goes the extra mile. I will definitely book her again.

Availability updated 4 days ago
Sitter Profile Image: Nicholas & Lauren R.
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Sitter Profile Image: Nicholas & Lauren R.
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Nicholas & Lauren R.

Two pet loving people
Madison, WI, 53704
3.6 mi. away
House Sitting
from
$50
per night
5 out of 5.0 stars
4 reviews
Profile image

Lauren and Nia were great with our pets and us! This was our first time using pet sitters and they really helped put us at ease through the process. With picture and video updates we knew our dogs and cats were having a good time and being well cared for. Highly recommend using them!

Availability updated 6 days ago
Sitter Profile Image: Jessica & Andrew B.
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Sitter Profile Image: Jessica & Andrew B.
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Jessica & Andrew B.
Rover 101

Experienced & Insured Sitter
Waunakee, WI, 53597
4.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
18 reviews
5 repeat clients
Profile image

Jessica was amazing from our first messages to her stay with my animals. Initially, I asked for references as I previously had a terrible experience on Rover and she was quick to provide me with the numbers of people she has sat for previously (with their permission). At our meet and greet my animals immediately took to her and her to them, and she was so comfortable even with their high excitement and noise levels. ;) During her stay with them, she kept in touch regularly with me and sent me so many pictures which I loved. I could tell she loved my animals which is always what you want from their caregiver. <3 My home was clean when I returned and, far more importantly, the animals had clearly been very loved on and wonderfully cared for! I recommend her so highly!! She is wonderful and my animals agree! :)

Availability updated 5 days ago
Sitter Profile Image: Louisa S.
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Sitter Profile Image: Louisa S.
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Louisa S.

Loving Pet Care Available
Sun Prairie, WI, 53590
4.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
5 reviews
2 repeat clients
Profile image

Louisa was excellent! She was so thorough in our meet and greet making sure she was aware of any and all needs Ollie might have. Ollie loved her right away which made me feel very comfortable. Louisa was great at communicating and sent pictures during the sit which I appreciated. Highly recommend her and will certainly have her care for Ollie in the future!

Availability updated 4 days ago
Sitter Profile Image: Ashley H.
Verified Enhanced Background Check
Sitter Profile Image: Ashley H.
Verified Enhanced Background Check

Ashley H.

Cat mom. Pet lover. EMT 🥰
Tenney-Lapham, Madison, WI, 53703
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
5 out of 5.0 stars
2 reviews

I have known Ashley for over 5 years. She is one of the most responsible person I know. She used to have a dog, and I have seen how much love and care she gave him. She is currently a cat mom that loves to spoil him with affection and love. Ashley loves the outdoors, so I have no doubt in my mind that she will be an excellent candidate to walk all the precious puppies in the neighborhood! She also has an experience working at a vet clinic, so she has a eye for detail, and experience to understand the pets needs. I would trust her with all of my own pets!

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

Joshua D.

Unlock Tail-Wagging Joy
Hawthorne, Madison, WI, 53704
3.3 mi. away
House Sitting
from
$30
per night
5 out of 5.0 stars
6 reviews
2 repeat clients
Profile image

Josh was wonderful! Our dog can be wary of new people, but Josh took the time to get to know him and let Coqui warm up to him slowly. He was respectful of our property (left our house so clean), was highly responsive, and communicative. We will definitely hire Josh again!

Availability updated today
Sitter Profile Image: Karrie G.
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Sitter Profile Image: Karrie G.
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Karrie G.

Flexible, kind-hearted, loving
Waunakee, WI, 53597
4.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
2 reviews

Karrie is very reliable and will do what's best for the family & pets! She is kindhearted and thoughtful person that is always willing to help out. Karrie LOVES to snuggle up on the couch w/ them too! :)

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

Annmarie S.
Star Sitter

Gentle and Loving for All Animals
Emerson East, Madison, WI, 53704
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
17 reviews
6 repeat clients
Profile image

Annemarie was a WONDERFUL dog sitter for my pup! She was so attentive and kept me informed the entire time, and Laika absolutely adored her. I will definitely be rebooking!

Availability updated today
Sitter Profile Image: Samantha S.
Verified Enhanced Background Check
Sitter Profile Image: Samantha S.
Verified Enhanced Background Check

Samantha S.

Easy, consistent pet care!
Madison, WI, 53704
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
1 review

Sam took amazing care of our pets! We have 2 dogs and a cat, all with very different personalities. She got to know all of them and get each one exactly what they need. Even if it’s been a while between visits, our pets are so excited to see her and get their personalized attention. I couldn’t recommend Sam enough!

Availability updated today
Confirmed availability for Labor Day Weekend

How Rover works

  1. 1. Search

    Read verified reviews and choose a house 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 house and 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?

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

  • Reservation protection

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

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

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