House Sitting in Wind Point

Find a loving house sitter to watch over your pets and your home.

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Top rated Wind Point house sitters

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Ky A.
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Ky A.
Star Sitter
from
$45
per night
5.0 out of 5 stars
47 reviews
18 repeat clients
6 years of experience
Mt Pleasant, WI, 53406

Such great care! Ky was so friendly and kind to my pups. She kept them company, made sure they had lots of love and treats, and communicated frequently on their status. I would absolutely book her again.

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Teresa F.
Sitter Profile Image: Monica L.
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Monica L.
Star Sitter
from
$69
per night
5.0 out of 5 stars
22 reviews
8 repeat clients
12 years of experience
Racine, WI, 53402

We were extremely pleased with the diligent care Monica provided for our 4-year-old Miniature Australian Shepherd. She did an excellent job not only watching Jaco, but also taking great care of our home while we were away. It gave us real peace of mind knowing everything was in such good hands. We would absolutely use Monica again and highly recommend her to others.

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Janine B.
Sitter Profile Image: Daniel B.
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Daniel B.
from
$40
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
30 years of experience
Caledonia, WI, 53402

Daniel was a reliable dogsitter at our house. Our dog loved him, as evident with Cali sitting at his feet even when we returned. Daniel did give Cali additional outdoor time, which was a treat. Daniel also went beyond the call to receive the shipment of our new lawnmower and see that it was sheltered in our garage.

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Elaine J.
Sitter Profile Image: Emily & Juliana M.
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Emily & Juliana M.
Star Sitter
from
$40
per night
5.0 out of 5 stars
5 reviews
4 repeat clients
8 years of experience
Racine, WI, 53405

About: I go by my middle name, Catherine, and you can call me Cat! Despite the name, I’m a dog fanatic! I have worked extensively with dogs of all ages as well as a wide variety of breeds including shepherds, sighthounds, hunting companions, terriers, and more! Most of my formal training experience was in Utah, from 2018-2021, and I have been continuing to chase my passion for dogs as a freelancer ever since! My Golden partner, Jelly, and I have been a service dog team for over 8 years - and we’ve gone on to mentor several service pups in training! Though she’s on the road to successful retirement now, Jelly is a testament to my love for dogs and my skill for training and bonding with them. It’s my goal to become an officially credentialed behavioralist! I know better than anyone that each and every dog is a unique (and oftentimes particular) soul. That’s why I take their parents’ guidelines to heart, because you know them best! I am also highly fluent in the ways dogs communicate, as well as how best to communicate back! I’m trained in basic grooming practices, from nail trims, to de-sheds, baths, and coat clipping! I have worked at board & train facilities as well as with independent trainers, and am highly experienced with virtually all training tools. I implement operant conditioning as my primary training philosophy - with adjustments made to suit an individual’s personality and drive. I am a full-time dog walker/sitter, freelance trainer, artist, and mom to 2 dogs, 2 cats, and a gecko. Routine is very important to me! I keep to a firm break schedule daily for my animals’ feeding, potty, exercise, and training. On weekends I am almost always home for the day, and I like to do socialization outings with my dogs on Saturday mornings! Your dog’s safety comes first and foremost. I am professionally experienced at listening to and commanding groups of up to 30 dogs, so I’m an expert at reading body language and taking preemptive action. I take care of other dogs as if they were my own! I know how important our furred companions are to us, and can follow your care instructions to a T.

Sitter Profile Image: Nichole B.
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Nichole B.
from
$56
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
15 years of experience
Racine, WI, 53405

Nicole did a great job taking care of our pack. She was very communicative with us. She sent pictures along the way and made sure all of our dogs were well taken care of. Left us some pictures when we got home as well to see how they did. Great experience and allowed us to enjoy our vacation stress free. Thanks!!

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Patrick M.
Sitter Profile Image: Kelly T.
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Kelly T.
from
$40
per night
5.0 out of 5 stars
24 reviews
10 repeat clients
42 years of experience
Racine, WI, 53403

Kelly was amazing for an extended stay at our house, watching our Australia Shepherd and two cats. Kelly was responsive and thorough with updates. We felt at ease for our whole trip knowing that Kelly was there to keep our fur babies safe and happy while we were gone. Great communication and just a really kind, thoughtful person. We hope to book her again for future needs! 😊

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Rachel & Ricky S.
Sitter Profile Image: Andrea H.
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Andrea H.
from
$45
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
35 years of experience
Racine, WI, 53402

About: I have ample space in my home to care and love your pet. As a dog owner myself, I have the necessary skills to care for your dog and give them the exercise and mental stimulation they need daily. My husband and I also foster dogs so we am very capable to handle new dogs in our home. He also works from home so your dog will always have someone around to care for them. I’d love to meet and have fun with your pet! I am currently working full-time but have ample time to play with your babies. I have no children except for my dog, so your pet will get a lot of attention. I am available for boarding anytime and walks or playtime after 3 pm. I have a fully fenced yard to keep your pups safe. And inside, i have plenty of room to play and I have crating options if needed or wanted.

Sitter Profile Image: Genevieve S.
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Genevieve S.
from
$30
per night
8 years of experience
Racine, WI, 53402

About: Have administered specialized medicine to senior animals for ongoing diseases such as kidney disease and hyperthyroidism. Was very diligent nursing my senior kitty before he passed. I work and go to school so my schedule varies but I always have some nights and mornings free each week that I would love to use on animals. I understand and respect animals boundaries and try my best not to encroach them. I've also mastered the "foot as barrier" approach when opening doors.

Sitter Profile Image: Michelle Z.
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Michelle Z.
Star Sitter
from
$65
per night
5.0 out of 5 stars
38 reviews
12 repeat clients
3 years of experience
Sturtevant, WI, 53177

Michelle was great with our 2 dogs. One dog is very shy, and nervous. Michelle gave her the space & time, to be comfortable with her. She took great care of the dogs, as well as, our home. She was great at communicating, sending updates, and pictures. We'll definitely be using her again.

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Jean B.
Sitter Profile Image: Samantha I.
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Samantha I.
from
$55
per night
5.0 out of 5 stars
4 reviews
10 years of experience
Kenosha, WI, 53144

Sam was great! Got back to happy dogs. She went above and beyond for us….getting our chickens food. Thanks Sam!

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Jennifer A.
Sitter Profile Image: Ashanty D.
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Ashanty D.
from
$28
per night
4 years of experience
Racine, WI, 53405

About: Ive been around animals for a decent part of my life. I’ve grown fond of having animals around, with 3 of my own kitties. I’m very diligent and patient with all animals. I can handle pups that pull. I’m versatile and work with all breeds. I strive to satisfy not only you , but also your pups. I would love to be a part of your fur babies journey!! :) I am fully available and very flexible with scheduling. I’d love to grow in experience and gain the skills I need to best take care of your pets(Home Experience Not Professional) I’m always available to take a stroll, play, and hang out with your fur babies. I will do my best to keep them happy and let them sight see. Thank you for the opportunity. I will always respect your space and follow the directions you give me. I appreciate good communication so that I can give the best service.

Sitter Profile Image: Hope J.
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Hope J.
from
$75
per night
1 year of experience
Racine, WI, 53402

About: I provide loving, reliable pet care tailored to each animal's unique needs. I find joy in making the pet feel safe, comfortable, and genuinely cared for while you're away. My goal is to treat every pet like they are my own, with plenty of attention, patience, and updates so you can feel at peace. I currently work part-time, which gives me plenty of flexibility and availability to fit your pet's needs into my schedule. This allows me to provide attentive care, stick to routines, and spend quality time with your pet without feeling rushed. My goal is to welcome every pet with open arms and lots of love, treating them like part of my own. I focus on making them feel safe, comfortable, and happy while giving them plenty of attention and affection.

Sitter Profile Image: Madalyn R.
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Madalyn R.
Star Sitter
from
$70
per night
5.0 out of 5 stars
12 reviews
7 repeat clients
7 years of experience
Sturtevant, WI, 53177

About: With over 7 years of hands-on dog sitting experience, I’ve cared for pups/kitties of all breeds, sizes, and temperaments—from energetic puppies to mellow seniors. I’ve handled everything from daily walks and medication administration (pills only) to overnight stays and longer holiday care. I prioritize creating a safe, loving environment that keeps their regular routine. Whether it’s fetch in the park or quiet cuddle time, I tailor care to each dog’s unique needs and personality. My schedule is open and flexible, which means I’m available for extended bookings, weekend getaways, *most* holidays, and all the in between’s. I’m here when you need me, morning, afternoon, or evening—no rigid time blocks, just dependable availability. Whether you’re heading out of town or working long hours, I’m ready to jump in with consistent, loving care. Pet parents can count on me to adapt to their routines and provide reliable service every day of the week. Safety and trust are the foundation of everything I do. I never leave dogs unsupervised in unsafe areas, and I only use the approved pups gear. I stay in close contact with pet parents, offering regular updates, pictures, and messages (if asked for) for peace of mind. With seven years of trusted pet care under my belt and a strong sense of responsibility, I treat your dog as if they were my own. Your pet’s wellbeing is always my top priority.

Sitter Profile Image: Joseph F.
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Joseph F.
Star Sitter
from
$70
per night
4.9 out of 5 stars
40 reviews
9 repeat clients
25 years of experience
Oak Creek, WI, 53154

Joe was amazing with our 4 furry toddlers! We've never really went on vacation because of our dogs and fears of boarding our dogs. Joe sent nearly daily updates, some pics and videos of them having a great time without us. He's super responsive to messages and very patient with people and our crazy pack of 4. Thanks again for allowing us to have a worry free 1st vacation!

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Samantha S.
Sitter Profile Image: Anik Z.
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Anik Z.
from
$50
per night
4 years of experience
Yorkville, WI, 53126

About: Hello! I study Vet Science at UW Madison and have extensive experience in both dog and cat humane societies, kennels, and have had dogs my whole life and cats for 3 years now. My dogs Jojo and Jagger are very energetic, and Indy is my tortie and the love of my life :) I tend to work weekends at my families business but can change my availability based on how familiar I get with your pet(s). I am always available to talk and will respond quickly to messages! I love to engage with pets and learn their body language, I will always have a ball or stick while walking your dog, but also understand when they need a break. My priority is making them feel as at home as possible, while earning experience in the field I love. I have patience for both cats and dogs, and will watch carefully to not over pet, play, or initiate with shy animals. Tell me more about your pet to help me help them be as comfortable as they can be!

Sitter Profile Image: Paige P.
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Paige P.
from
$55
per night
5.0 out of 5 stars
2 reviews
9 years of experience
Mount Pleasant, WI, 53406

About: (I go by Dakota, so some testimonies might call me that) I started off pet sitting for neighbors when I was about 14. I would feed, let out, and walk the dogs, and feed and clean cat litter boxes as needed. I moved up to dog sitting for family friends, old coworkers, and coworkers’ clients about three years ago, where I would do the same, and even bathe dogs if needed. I have experience pet sitting rodents and reptiles as well! I am currently not working a job, so I have all the time to give your babies the love and attention they need and deserve! I have experience with body language in dogs, so I can always tell when your baby is happy, upset, or uncomfortable. If you don’t have a fenced in yard, no problem! I can take your fur baby on a secure leash outside!

Sitter Profile Image: Delaney W.
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Delaney W.
from
$75
per night
5.0 out of 5 stars
18 reviews
4 repeat clients
10 years of experience
Kenosha, WI, 53144

Delaney is reliable friendly and very loving to our pug Louis. Very caring and attentive. Definitely someone I will always have be with our sweet boy.

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Kate S.
Sitter Profile Image: River W.
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River W.
from
$50
per night
5.0 out of 5 stars
21 reviews
8 repeat clients
2 years of experience
South Milwaukee, WI, 53172

River was amazing with our dogs. She gave them space until they felt comfortable with us not being home. She was great with communication and giving us updates while we were gone. It really made us feel comfortable being able to take a vacation without worring about the dogs. I highly recommend river they are amazing!

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Angela C.
Sitter Profile Image: Carolina G.
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Carolina G.
from
$50
per night
4.9 out of 5 stars
35 reviews
7 repeat clients
9 years of experience
Cudahy, WI, 53110

We were pleased with Caroline😊 She was attentive to Petey and helped him adjust to a new person caring for him. Petey is a happy dog and Caroline was great at getting him to play and took him for several walks! We felt she kept us posted with notes and pictures. We honestly can’t think of anything she could improve-Our Petey was well cared for and given plenty of attention😊

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Richard /Katrina M.
Sitter Profile Image: Jack S.
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Jack S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
31 reviews
8 repeat clients
7 years of experience
Cudahy, WI, 53110

About: Frequent walker that would be happy to have a dog join. I also have a backyard that I maintain all of the time for use. I do not have a dog of my own and typically only watch one dog (or two if you have two) at a time leaving your dogs needs at the priority! I work remote so will always be able to be responsive when sitting. Also have a 700+ day 10,000 step streak so doing lots of walking currently! Handle and escalate and concerns to owner when appropriate and I feel any sorts of hesitations. Thoughtfully, decisively, and neutrally investigate Trust & Safety cases with high complexity and high sensitivity while maintaining customer satisfaction! As a reminder I do not have a fenced in yard so all outside time will be through walks!

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Wind Point pet parents share their Rover experiences

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5.0 out of 5 stars

We were extremely pleased with the diligent care Monica provided for our 4-year-old Miniature Australian Shepherd. She did an excellent job not only watching Jaco, but also taking great care of our home while we were away. It gave us real peace of mind knowing everything was in such good hands. We would absolutely use Monica again and highly recommend her to others.

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Janine B.
House Sitting
5.0 out of 5 stars

Heidi was amazing from start to finish. She took great care of my dogs and went above and beyond by bringing them toys, which they absolutely loved. You can tell she really cares and pays attention. On top of that, we came back to a clean, well-kept house, which I really appreciated. Everything was handled professionally and with care. I’d definitely trust her again and highly recommend her to anyone looking for a reliable and thoughtful sitter.

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Jen M.
House Sitting
5.0 out of 5 stars

Andrea was absolutely incredible! She stayed at my house with my dog, Leo, and I could not have asked for a better sitter. From the very beginning she was communicative, reliable, and so easy to work with. I got regular updates and photos, and Leo looked completely happy and spoiled the entire time. It’s such a rare comfort to leave your home and your dog in someone’s hands and feel zero stress — but that’s exactly what Andrea provides. She treated my house with respect, left everything spotless, and took care of Leo like he was her own. I came home to a happy dog, a tidy home, and total peace of mind. I’ll absolutely be booking with her again. If you’re looking for someone trustworthy, caring, truly exceptional, and also just a cool girl, Andrea is the one!

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Megan L.
House Sitting
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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!

The median cost per night for house sitting in Wind Point is $50

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.

Sitters in Wind Point average 5
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Wind Point on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Wind Point house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 960 house sitters in Wind Point. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 85% of Wind Point house sitters respond in under an hour.

House sitters in Wind Point have an average of 15 years of experience. House sitters with repeat customers have an average of 5 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Wind Point.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Wind Point house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.