House Sitting Wind Point

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Over 5
pet parents in Wind Point have booked house sitting

Wind Point, Find top rated house sitting

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

1 / 1
Sitter Profile Image: Heidi B.
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Heidi B.
from
$50
per night
5.0 out of 5 stars
45 reviews
15 repeat clients
32 years of experience
Caledonia, WI, 53402

Heidi was amazing. She was very accommodating in terms of finding a time for a meet and greet. When my son decided he wanted to entertain her and have her attention as I showed her around, she was a great sport. She was super non-judgmental about the state of our house, and put me at ease. She was great with our pets while we were gone, and sent adorable photos. When we got home, I found that she had washed all of the odd dishes we hadn’t had a chance to wash before we left. She also shoveled the walkway! I will absolutely be reaching out to her again, next time we go on vacation.

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Cassandra H.
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 fantastic. Was happy to stay at my house with my two dogs and my bird the week of Christmas and take care of them all and my house. I would highly recommend her for house sitting or pet sitting.

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Beverly B.
Sitter Profile Image: Michelle Z.
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Michelle Z.
Star Sitter
from
$70
per night
5.0 out of 5 stars
46 reviews
14 repeat clients
3 years of experience
Sturtevant, WI, 53177

Michelle was prompt in her arrival and provided excellent care and companionship for Holly while we were gone for the day. We were very happy with this visit.

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Lori K.
Sitter Profile Image: Monica L.
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Monica L.
Star Sitter
from
$75
per night
5.0 out of 5 stars
27 reviews
9 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: Carolina G.
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Carolina G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
40 reviews
8 repeat clients
9 years of experience
Cudahy, WI, 53110

Carolina was super respectful of all of our instructions for caring for the cat and dog. She sent many pictures and videos along with detailed updates. We have no question that they were well taken care of and they were happy when she was here.

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Julia M.
Sitter Profile Image: Anna S.
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Anna S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
18 reviews
4 repeat clients
5 years of experience
Oak creek, WI, 53154

Anna was amazing!! She sent us photos and updates every day and cared for Cleo as if she were her own dog. She was incredibly attentive, super clean, and even left our apartment looking better than when she arrived. We couldn’t have asked for a better sitter.

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Dayne R.
Sitter Profile Image: Melissa M.
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Melissa M.
from
$35
per night
5.0 out of 5 stars
57 reviews
16 repeat clients
12 years of experience
Mount Pleasant, WI, 53406

Mel has been the absolute best sitter I’ve ever had for my dog. He looks just as happy with Mel as he does with me and his dad. I felt so assured and happy that Leo had his own little vacation. My neighbors told me they played with him outside all day, which is his favorite. 10/10 will 100% book again!

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Megan L.
Sitter Profile Image: Madelyn G.
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Madelyn G.
from
$27
per night
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Raymond, WI, 53126

Madelyn was great when she watched our dog Cooper when we were on our week long road trip. She was very communicative and we could tell she took great care of Cooper. We definitely will book her again.

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Tim and Molly H.
Sitter Profile Image: Genevieve S.
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Genevieve S.
from
$35
per night
4.8 out of 5 stars
4 reviews
1 repeat client
8 years of experience
Caledonia, WI, 53126

She was exceptional with my baby, Molly. Molly is normally extremely slow to warm up to people but she immediately took to Genevieve. She kept me updated with pictures and texts, followed my instructions, and most of all kept my girl safe from a murderous wasp and loneliness while I rudely went on vacation without her. There’s nothing better than a cat sitter who loves your girl as much as you do.

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Hailey M.
Sitter Profile Image: Alexy & Kayla G.
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Alexy & Kayla G.
from
$40
per night
4.9 out of 5 stars
89 reviews
25 repeat clients
4 years of experience
Milwaukee, WI, 53110

Alexy & Dylan were great. Loved getting all the pictures and updates while we were away. Will definitely be using them again! Thank you so much!

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Kassandra W.
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: Travis H.
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Travis H.
Star Sitter
from
$80
per night
5.0 out of 5 stars
370 reviews
113 repeat clients
35 years of experience
Milwaukee, WI, 53212

We met Travis for a meet and greet ahead of time and he was always very attentive, friendly, communicative, and willing to listen. He took great care of our pup for a week and kept our apartment just how it was when we left. We're looking forward to working with him again in the future!

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Caroline W.
Sitter Profile Image: Joshua C.
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Joshua C.
from
$50
per night
4.8 out of 5 stars
19 reviews
9 repeat clients
7 years of experience
Kenosha, WI, 53142

This was the first time using Rover. I could not be more pleased with the individual we picked when we chose Josh!!! He was readily available. He kept in great communication with us throughout the entire process from booking to his departure after watching our pups. He cleaned up and left house clean and tidy. Even kept the pups safe during a tornado warning. Cannot wait to book again with Josh!

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Julie F.
Sitter Profile Image: Emma B.
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Emma B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
23 reviews
6 repeat clients
20 years of experience
Cedarburg, WI, 53012

Emma is amazing! I loved that she wanted to meet me and Lacey before she accepted a job. It was important to her that we were all on the same page. I was able to talk about Laceys needs and routine in person, which really made me feel at ease. When the weekend came for her to stay at our house I was completely comfortable leaving Lacey in her care. She gave me updates and pictures which was great. Thank you Emma!!!!

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Paula R.
Sitter Profile Image: Jalyn K.
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Jalyn K.
from
$35
per night
5.0 out of 5 stars
4 reviews
1 repeat client
4 years of experience
Cudahy, WI, 53110

Great service and sent photos of kadee for her stay. Checked in regularly as well. Will use again

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Tom G.
Sitter Profile Image: Liz P.
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Liz P.
from
$60
per night
5.0 out of 5 stars
143 reviews
42 repeat clients
6 years of experience
Riverwest, Milwaukee, WI, 53212

Liz was great at following instructions and was super receptive to any feedback or request. She took care of my boys and the house. She kept me updated and seemed to really care for the boys.

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Vanessa N.
Sitter Profile Image: Daniel B.
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Daniel B.
from
$55
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
30 years of experience
Caledonia, WI, 53402

Daniel was super accommodating for a last minute booking, and took good care of the animals and house! Everyone was super relaxed when we came home.

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Beka V.
Sitter Profile Image: Fatima B.
Verified Enhanced Background Check
Fatima B.
from
$35
per night
5.0 out of 5 stars
8 reviews
1 repeat client
2 years of experience
West Allis, WI, 53214

Fatima was amazing to work with. I booked her on short notice before the holiday when my original plans fell through. She offered and made it a priority to come do a meet & greet on days notice. I’m always a little nervous when using a new sitter especially when they stay at mine, but my mind was at ease immediately when I met her. I could tell she has a big heart and really cares for animals. She followed all instructions and she went above and beyond spending time with Diesel doing his favorite activities (walks, playing fetch, swimming, etc.). She was incredibly communicative and sent a lot of pictures and videos which was much appreciated. As a former Rover sitter and a frequent user of Rover’s services, I can confidently say that Fatima is one of the best sitters I’ve come across. I will definitely be using her in the future and have already recommended her to others looking for sitters. Thank you Fatima!!!

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Alex S.
Sitter Profile Image: Terri T.
Verified Enhanced Background Check
Terri T.
from
$70
per night
4.9 out of 5 stars
85 reviews
23 repeat clients
20 years of experience
Burlington, WI, 53105

Terri watched my babies for 2 weeks recently while I was in Europe. I was a nervous nelly about leaving them behind. I certainly didn’t want to put them in a kennel / prison. Terri kept me constantly updated with texts and photos on how they were doing. Most importantly she kept them on the small routines they were used to so that they would be less stressed. I too was less stressed. She did a great job. I would recommend her highly.

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Michael W.
Sitter Profile Image: Jamila M.
Verified Background Check
Jamila M.
from
$65
per night
4.9 out of 5 stars
98 reviews
29 repeat clients
27 years of experience
Washington Heights, milwaukee, WI, 53208

Jeremy was amazing. He was prompt, insanely responsive, and went above and beyond when we forgot to leave our son’s soccer stuff out for pick up. He even ran to purchase new shin guards when he couldn’t find them for us. This man is truly amazing and we appreciate him watching our three puppies. Our shepherd is usually super depressed when we are away and he looks so happy in all the pictures we received.

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

Pet parents share their Rover experiences - Wind Point

1 / 1
5.0 out of 5 stars

This is the second time Heidi has housesit for our dog and two cats, and they were well looked after during our week and a half away. She went above and beyond for one of our cats and everyone was happy when we returned. Would definitely recommend her!

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Beka V.
House Sitting
5.0 out of 5 stars

Daniel was super accommodating for a last minute booking, and took good care of the animals and house! Everyone was super relaxed when we came home.

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Beka V.
House Sitting
5.0 out of 5 stars

We had her sit our two pups in our home for a long weekend and she was great! Our pups and our home were well looked after.

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Dom D.
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
1 / 1
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Wind Point

Select a filter and find qualifying sitters offering house sitting.

Sitters in Wind Point average 4
repeat house sitting clients

FAQs for House Sitting - Wind Point

Frequently asked questions about Rover

The average cost for House Sitting in Wind Point on Rover is $32.1 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of August 2026, there are 1,216 sitters on Rover offering House Sitting across Wind Point. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Wind Point walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Wind Point maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Wind Point choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Wind Point. On Rover:

  • 88% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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