House Sitting in Windsor

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Top rated Windsor house sitters

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Sitter Profile Image: Megan B.
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Megan B.
from
$35
per night
5 out of 5.0 stars
19 reviews
5 repeat clients
15 years of experience
Sun Prairie, WI, 53590

Megan took excellent care of our Murphy for a weekend away. She arrived as planned and spent quality time with Murphy each day, and provided frequent and thorough updates, including pictures! We won’t hesitate to book Megan again to watch Murphy - highly recommend!

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Rachel B.
Sitter Profile Image: Tiana B.
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Tiana B.
Star Sitter
from
$50
per night
5 out of 5.0 stars
5 reviews
3 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
$29
per night
5 out of 5.0 stars
8 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: Terry K.
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Terry K.
from
$60
per night
5 out of 5.0 stars
37 reviews
10 repeat clients
30 years of experience
Middleton, WI, 53562

Terry was fantastic! She was great with our dogs and a pleasure to work with. She was a perfect houseguest and our dogs were perfectly looked after. We can’t recommend Terry enough.

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Eric W.
Sitter Profile Image: Sidney R.
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Sidney R.
Star Sitter
from
$50
per night
5 out of 4.9 stars
60 reviews
20 repeat clients
20 years of experience
Middleton, WI, 53562

Sydney did a fantastic job being with our dog, Della. She shared comments with us while we were gone. This made us feel confident that the care she provided was important to her. We would definitely ask Sydney to care for our dog again! Thank you.

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Kevin A.
Sitter Profile Image: Leah B.
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Leah B.
from
$55
per night
5 out of 4.7 stars
65 reviews
26 repeat clients
6 years of experience
Monona, WI, 53716

Leah you were amazing. Thank you for your flexibility and quick responses. I felt so comfortable leaving my giant boys with you. I can tell they felt very comfortable. We really appreciate you!

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Allison S.
Sitter Profile Image: Travis M.
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Travis M.
Star Sitter
from
$65
per night
5 out of 5.0 stars
24 reviews
5 repeat clients
15 years of experience
MONONA, WI, 53713

We have never left our boy, Griffin for more than a couple of days before. We went on a two week trip and hired Travis to watch our big sheepadoodle. He was incredible! He sent us pictures and videos of Griffin at the dog park and around the third day, Griffin was giving him his paw and Travis was loving on him. We then received a picture of Griffin on the bed Travis used…. That sealed it…. Griffin loves him! We do too! We couldn’t have asked for a better sitter for our boy❤️

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Elaine W.
Sitter Profile Image: Caoylin C.
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Caoylin C.
from
$40
per night
5 out of 4.9 stars
10 reviews
2 repeat clients
2 years of experience
DeForest, WI, 53532

Carolyn was great! She checked in keeping me posted on how Ellie was doing, and was open to staying with her longer while it was storming. Will definitely use her again.

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Bridget H.
Sitter Profile Image: Morgan D.
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Morgan D.
from
$40
per night
5 out of 5.0 stars
4 reviews
10 years of experience
Sun Prairie, WI, 53590

Morgan is great with our anxious little dog! She is gentle and moves at his pace and really makes him and us feel comfortable!

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Michala M.
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 my diabetic dog who had some surprise additional restrictions after a tooth removal earlier that week. Additionally, she left my house spotless.

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Margaret W.
Sitter Profile Image: Katelyn C.
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Katelyn C.
Star Sitter
from
$28
per night
5 out of 5.0 stars
9 reviews
2 repeat clients
10 years of experience
Sun Prairie, WI, 53590

About: I have had dogs in my life since I was a baby! From labs, hound, shepherds, and plenty of breeds in between, I love to meet new dogs and make them my new bff. Feeding, walks, playtime, potty breaks, you name it, I can do it. I even worked in the office of a dog training company for awhile! I have plenty of stories to share :) I work 35 hours a week at my full time job, so I have some extra time that would be easily filled with pet care. I live in a very walkable neighborhood and would love to get my daily exercise while helping pets get theirs too. I have experience crating dogs, following through on commands, and recognizing when a dog needs space. I worked in the office for a dog training company for 2 years and know how and when to avoid risky situations. I’m strong and can handle most larger dogs.

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

This was my first time using Rover, and I appreciated Tina walking me through the process. I appreciated her daily updates, clear communication, and my house was as I'd left it.

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Heather E.
Sitter Profile Image: Karina M.
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Karina M.
from
$30
per night
5 out of 5.0 stars
20 reviews
4 repeat clients
5 years of experience
Marquette, Madison, WI, 53703

Karina took excellent care of our cat, dog, and home! Our dog is fairly nervous, and our cat required medication but Karina handled it all with patience and care and kept us updated with photos and texts throughout the weekend. We’ll definitely be reaching out next time we need someone to look after them!

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Kelsey W.
Sitter Profile Image: Jessa E.
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Jessa E.
from
$40
per night
5 out of 5.0 stars
5 reviews
1 repeat client
3 years of experience
Madison, WI, 53714

12 out of 10. Jessa truly saved me with a last minute request after I had a few rover sitters canceled on me. She came and met my dogs and also was gracious enough to keep an eye on my garden. I will absolutely be using her in the future.

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Mackenzie S.
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
1 repeat client
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: Samantha M.
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Samantha M.
from
$45
per night
10 years of experience
Madison, WI, 53704

About: I’ve grown up surrounded by animals. I’ve dog sat several times over the span of a decade. I’ve cared for dog breeds of all ages, sizes and personalities. Whether it was daily walks, overnight stays, and followed detailed care routines. I also love to stay active and will provide long walks in the neighborhood or local parks! As a college student, I have a flexible schedule that allows me to plan my classes and study time around pet care. Whether it’s starting with a morning walk or stopping by in the afternoon. Typically I am available Monday-Friday. In clients houses, I make it my top priority to care for your space, respect your pets as I would my own home. I stick closely to your pets usual routine for feeding, walks and playtime. And I’ll always keep you updated with photos or messages to see how they’re doing.

Sitter Profile Image: Hayley K.
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Hayley K.
from
$30
per night
5 out of 5.0 stars
7 reviews
1 repeat client
2 years of experience
Waunakee, WI, 53597

About: I have been a huge animal lover since I was a kid. I volunteered at the local animal shelter in my college town for over a year, so I have experience with a variety of different dog breeds across a variety of different ages. As a volunteer, I was responsible for walking and socializing the dogs. I also took dogs out of the shelter for a day to get them experience in public. My family also have had dogs for my entire life, so I have experience with taking care of dogs at all ages. I live a very active lifestyle that allows me to take dogs out for the exercise that they need. I also like to follow specific schedules which helps avoid uncertainty in animal schedules. I care for pets in my home and others home in the way that the owner expects. It is important to keep training and care consistent for a pet so it avoids confusion for the pet. It is also important to understand the breed of the animal as every breed has different needs.

Sitter Profile Image: Emily B.
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Emily B.
Star Sitter
from
$50
per night
5 out of 5.0 stars
13 reviews
2 repeat clients
3 years of experience
Arlington, WI, 53911

Emily is so sweet and kind, we loved having her help us. I appreciated having her watch our pup while I was out of town. I have never had anyone outside of family house sit for me and was nervous. Emily took all my nerves away, she kept me updated throughout her stay and my home was as clean as I left it. Would recommend her to anyone and will definitely be a repeat customer!

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Brittani B.
Sitter Profile Image: Anna O.
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Anna O.
from
$45
per night
5 out of 5.0 stars
13 reviews
1 repeat client
15 years of experience
Waunakee, WI, 53597

Anna did a fantastic job with our fur kids. She was very good about sending us pictures and updates about how things were going, which I really appreciated because our dog Izzy wasn’t feeling great. Izzy and our 3 cats were well taken care of. We’re looking forward to having Anna again during our summer vacation trip for house sitting! She is great!

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Ginger R.
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Loving house sitters in your neighborhood

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Sitter Profile Image: Megan B.
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Sitter Profile Image: Megan B.
Verified Background Check

Megan B.

Owner Away? I’ll Sit, Stay and Walk
Sun Prairie, WI, 53590
4.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per night
5 out of 5.0 stars
19 reviews
5 repeat clients
Profile image

Megan took excellent care of our Murphy for a weekend away. She arrived as planned and spent quality time with Murphy each day, and provided frequent and thorough updates, including pictures! We won’t hesitate to book Megan again to watch Murphy - highly recommend!

Availability updated 7 days ago
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
2.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5 out of 5.0 stars
5 reviews
3 repeat clients
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Tiana was very dependable and took very good care of Hobbes

Availability updated today
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
11.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$29
per night
5 out of 5.0 stars
8 reviews
5 repeat clients
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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
Sitter Profile Image: Terry K.
Verified Enhanced Background Check
Sitter Profile Image: Terry K.
Verified Enhanced Background Check

Terry K.
Rover 101

Grandma love is on the way !!
Middleton, WI, 53562
11.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
37 reviews
10 repeat clients
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Terry was fantastic! She was great with our dogs and a pleasure to work with. She was a perfect houseguest and our dogs were perfectly looked after. We can’t recommend Terry enough.

Availability updated yesterday
Sitter Profile Image: Sidney R.
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Sitter Profile Image: Sidney R.
Verified Enhanced Background Check

Sidney R.
Star Sitter

They call me “The Pal Gal”!
Middleton, WI, 53562
13.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.9 stars
60 reviews
20 repeat clients
Profile image

Sydney did a fantastic job being with our dog, Della. She shared comments with us while we were gone. This made us feel confident that the care she provided was important to her. We would definitely ask Sydney to care for our dog again! Thank you.

Availability updated yesterday
Sitter Profile Image: Leah B.
Verified Enhanced Background Check
Sitter Profile Image: Leah B.
Verified Enhanced Background Check

Leah B.

I absolutely love to love dogs
Monona, WI, 53716
11.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 4.7 stars
65 reviews
26 repeat clients
Profile image

Leah you were amazing. Thank you for your flexibility and quick responses. I felt so comfortable leaving my giant boys with you. I can tell they felt very comfortable. We really appreciate you!

Availability updated 13 days ago
Sitter Profile Image: Travis M.
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Sitter Profile Image: Travis M.
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Travis M.
Star Sitter

Reliable, caring dog-lover
MONONA, WI, 53713
11.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
24 reviews
5 repeat clients
Profile image

We have never left our boy, Griffin for more than a couple of days before. We went on a two week trip and hired Travis to watch our big sheepadoodle. He was incredible! He sent us pictures and videos of Griffin at the dog park and around the third day, Griffin was giving him his paw and Travis was loving on him. We then received a picture of Griffin on the bed Travis used…. That sealed it…. Griffin loves him! We do too! We couldn’t have asked for a better sitter for our boy❤️

Availability updated 22 days ago
Sitter Profile Image: Caoylin C.
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Sitter Profile Image: Caoylin C.
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Caoylin C.

Top tier dog care!
DeForest, WI, 53532
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 4.9 stars
10 reviews
2 repeat clients
Profile image

Carolyn was great! She checked in keeping me posted on how Ellie was doing, and was open to staying with her longer while it was storming. Will definitely use her again.

Availability updated 23 days ago
Sitter Profile Image: Morgan D.
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Sitter Profile Image: Morgan D.
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Morgan D.

Energetic, respectful, and caring
Sun Prairie, WI, 53590
5.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
4 reviews
Profile image

Morgan is great with our anxious little dog! She is gentle and moves at his pace and really makes him and us feel comfortable!

Availability updated 10 days ago
Sitter Profile Image: Stephanie H.
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Sitter Profile Image: Stephanie H.
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Stephanie H.
Star Sitter

Dog lover pet spoiler
Eastmorland, Madison, WI, 53714
8.8 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 my diabetic dog who had some surprise additional restrictions after a tooth removal earlier that week. Additionally, she left my house spotless.

Availability updated 9 days ago
Sitter Profile Image: Katelyn C.
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Sitter Profile Image: Katelyn C.
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Katelyn C.
Star Sitter

Your dog’s new best friend
Sun Prairie, WI, 53590
7.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
5 out of 5.0 stars
9 reviews
2 repeat clients

Katie is always my first call to take care of my two dogs when I go out of town or just need someone to stop by to let them out. When my golden retriever underwent surgery and needed medication, Katie was meticulous in making sure he had everything he needed to stay healthy and happy. She’s also patient with my senior St. Bernard, who takes a little more time on walks and requires a bit more cleanup after meal times. When I have to leave my dogs at home, I feel completely at ease knowing they are in her capable hands. I would absolutely trust her with my dogs again in the future. If you are looking for someone reliable, responsible, and caring, Katie is the perfect choice to care for your furry friends!

Availability updated 2 days ago
Sitter Profile Image: Tina B.
Verified Background Check
Sitter Profile Image: Tina B.
Verified Background Check

Tina B.
Star Sitter

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

This was my first time using Rover, and I appreciated Tina walking me through the process. I appreciated her daily updates, clear communication, and my house was as I'd left it.

Availability updated 10 days ago
Sitter Profile Image: Karina M.
Verified Background Check
Sitter Profile Image: Karina M.
Verified Background Check

Karina M.

Dependably kind and reliable
Marquette, Madison, WI, 53703
9.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
20 reviews
4 repeat clients
Profile image

Karina took excellent care of our cat, dog, and home! Our dog is fairly nervous, and our cat required medication but Karina handled it all with patience and care and kept us updated with photos and texts throughout the weekend. We’ll definitely be reaching out next time we need someone to look after them!

Availability updated 6 days ago
Sitter Profile Image: Jessa E.
Verified Enhanced Background Check
Sitter Profile Image: Jessa E.
Verified Enhanced Background Check

Jessa E.

Dog walker
Madison, WI, 53714
7.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
5 reviews
1 repeat client
Profile image

12 out of 10. Jessa truly saved me with a last minute request after I had a few rover sitters canceled on me. She came and met my dogs and also was gracious enough to keep an eye on my garden. I will absolutely be using her in the future.

Availability updated yesterday
Sitter Profile Image: Jessica & Andrew B.
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Sitter Profile Image: Jessica & Andrew B.
Verified Enhanced Background Check

Jessica & Andrew B.
Rover 101

Experienced & Insured Sitter
Waunakee, WI, 53597
3.4 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 today
Sitter Profile Image: Louisa S.
Verified Enhanced Background Check
Sitter Profile Image: Louisa S.
Verified Enhanced Background Check

Louisa S.

Loving Pet Care Available
Sun Prairie, WI, 53590
5.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
5 reviews
1 repeat client
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 24 days ago
Sitter Profile Image: Samantha M.
Verified Enhanced Background Check
Sitter Profile Image: Samantha M.
Verified Enhanced Background Check

Samantha M.

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

Samantha is a very caring and pet loving person. She watched 4 of my dogs for a weekend without any problems. I trust her with my dogs and any other pet. She would be a great pet sitter!

Availability updated 4 days ago
Sitter Profile Image: Hayley K.
Verified Enhanced Background Check
Sitter Profile Image: Hayley K.
Verified Enhanced Background Check

Hayley K.

Experienced, Dedicated Dog Lover
Waunakee, WI, 53597
5.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
7 reviews
1 repeat client

Hayley loves dogs! We have always had a family dog and Hayley was taught from a young age how to interact and care for dogs. At college, Hayley volunteered at the LaCrosse County Humane Society. Twice a week she would help with the sheltered dogs. She was able to “check out” shelter dogs for a day. She would take them hiking and to other places to help them get adopted

Availability updated 5 days ago
Sitter Profile Image: Emily B.
Verified Enhanced Background Check
Sitter Profile Image: Emily B.
Verified Enhanced Background Check

Emily B.
Star Sitter

No dog too big or small
Arlington, WI, 53911
8.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
13 reviews
2 repeat clients
Profile image

Emily is so sweet and kind, we loved having her help us. I appreciated having her watch our pup while I was out of town. I have never had anyone outside of family house sit for me and was nervous. Emily took all my nerves away, she kept me updated throughout her stay and my home was as clean as I left it. Would recommend her to anyone and will definitely be a repeat customer!

Availability updated 89 days ago
Sitter Profile Image: Anna O.
Verified Enhanced Background Check
Sitter Profile Image: Anna O.
Verified Enhanced Background Check

Anna O.

Farm girl misses her pups! (& pigs)
Waunakee, WI, 53597
7.7 mi. away
House Sitting
from
$45
per night
5 out of 5.0 stars
13 reviews
1 repeat client
Profile image

Anna did a fantastic job with our fur kids. She was very good about sending us pictures and updates about how things were going, which I really appreciated because our dog Izzy wasn’t feeling great. Izzy and our 3 cats were well taken care of. We’re looking forward to having Anna again during our summer vacation trip for house sitting! She is great!

Availability updated today

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?

  • 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 house 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.

House Sitting FAQs

Frequently asked questions about Rover