House Sitting Cheeseville

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Cheeseville, 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.

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Sitter Profile Image: Sydney G.
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Sydney G.
Star Sitter
from
$38
per night
5.0 out of 5 stars
13 reviews
4 repeat clients
2 years of experience
West Bend, WI, 53090

Sydney was wonderful! She sent me pictures of my fur babies and had good communication. I didn't worry about leaving my three pets in her care. It was so nice to come home to my pets happy faces and a clean home. Thank you Sydney.

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Amy B.
Sitter Profile Image: Tarah & Firaas F.
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Tarah & Firaas F.
from
$40
per night
5.0 out of 5 stars
33 reviews
13 repeat clients
10 years of experience
Fredonia, WI, 53021

This was my first time using Rover and I couldn't have been happier having Tarah take care of my dogs. She was professional, courteous, and just loved on my dogs like I do. She even handled my deaf special needs boy who is very active. :)

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Monica S.
Sitter Profile Image: Faith B.
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Faith B.
from
$55
per night
5.0 out of 5 stars
69 reviews
13 repeat clients
20 years of experience
Jackson, WI, 53037

Faith did an amazing job with our Bruno!! This is our second time having Faith watch our dog and we are just as happy as we were the first time. Bruno was well cared for and very relaxed and happy when we got back home which shows how well he did with Faith. She was very good at keeping us updated with photos and messages. Asked questions when anything needed to be clarified. She even let us know she put out our trash to be picked up! The house was spotless when we returned, clean and tidy. But most of all Bruno had a great time with Faith and we will definitely use her again for our next vacation!!

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Benedetta B.
Sitter Profile Image: Paul S.
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Paul S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
89 reviews
29 repeat clients
20 years of experience
Germantown, WI, 53022

Paul did an awesome job taking care of our elderly dog. It was difficult to leave her with a new dog sitter (our usual sitter got a new job) but after meeting Paul and seeing that Rheyah was immediately comfortable with him, we felt confident that he would take good care of her. Paul made sure that Rheyah took her medicine multiple times per day, fed her a special diet and even gave her a partial bath every other night to treat her chronic skin condition. He also took her for 2 walks per day when the weather permitted. Paul’s frequent photos and descriptions of what he and Rheyah were doing helped to calm my anxiety about leaving her with someone new. Not only did Paul take care of Rheyah, but he also fed my fish and managed to keep my not-so-healthy plants alive! We are very grateful that Paul’s profile came up on Rover and that he agreed to take care of Rheyah so that we could attend our granddaughter’s 1st birthday. We highly recommend Paul to anyone who needs a conscientious caring pet sitter!

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Ann Marie H.
Sitter Profile Image: Jeanee S.
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Jeanee S.
from
$65
per night
5.0 out of 5 stars
20 reviews
9 repeat clients
25 years of experience
Cedarburg, WI, 53012

Jeanee was the most incredible dog sitter we have ever had. Lilly got to go on many adventures and walks. Once Lilly got to know Jeanne, she asked if Lilly could with on errands, Lilly loves car rides. I suggested if she wanted to take her home to introduce Lilly to her furbaby - she could give it a shot. Keeping in mind that Lilly is food & person possessive and can be aggressive with older dogs, but Jeanee knew exactly how to handle her. It worked out so well that Lilly stayed at her home the remaining 6 days! Her dog really enjoyed having another dog around. She took Lilly's bed, food, treats and favorite stuffie to her house, so Lilly felt right at home. It really helped Lilly, she wasn't constantly watching for us, missing us and she ate so well. We had constant communication and updates. Anytime I sent a message she responded very quickly. This was the most confident and secure we have ever felt on our vacation. It made for a very relaxing and fun vacation. Knowing we now have an incredible sitter for Lilly, we are looking to book future vacations. 100% recommend!! Your furbaby will be in incredible hands!!

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Michele M.
Sitter Profile Image: Diane & Dale G.
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Diane & Dale G.
from
$60
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
30 years of experience
Random Lake, WI, 53075

Diane was a fantastic dog sitter! My pup can be shy around people and dogs he is not familiar with. Diane had Kona sitting on her lap minutes after she arrived to watch him. She took him out for walks multiple times in the 24 hours she was with him. She sent pictures showing how relaxed Kona was with her. I felt like a family member was watching him! I will certainly be contacting Diane in the future to watch my pup! She is a true dog lover!

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Robin S.
Sitter Profile Image: Kailie K.
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Kailie K.
from
$40
per night
1 repeat client
5 years of experience
West Bend, WI, 53090

About: My name is Kailie, and I am 20 years old. I have grown up around dogs my entire life, and I have always loved them! I was always the little kid who would go up to strangers asking to pet their dog, and I still will! Dogs deserve love too! I have one adorable Shepherd/Terrier mix at home, who is a little over one years old! I have trained her to do a lot of tricks, including how to give hugs and kisses on command! She definitely is a wild one though! She loves to play tug of war, and ball, and if she doesn’t, she gets a little sassy! Her absolute favorite thing though is to play with other dogs! Especially my sister’s and brothers’s dogs! Whenever they need someone to watch their dogs, I’m normally the first call! My dog definitely loves having the company, but I know my siblings are also just happy to have their dogs in a loving and caring home! I work full time, 2-11pm, and I get an hour and 15 minute lunch break, so I can always let dogs out on my lunch break if needed! I have off every Saturday and Tuesday as well, so I’m free those days! My dog normally just roams the house while we are gone. When I let her outside she gets put on a leash. We do let her free roam with a shock collar on when we play ball though. However, I am willing to do whatever fits your routine and whatever your dog is comfortable with! If a crate works best for them, or if they get let out in a fenced yard, then that’s what we will do! Whatever works for you and your dog!

Sitter Profile Image: Amanda K.
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Amanda K.
Star Sitter
from
$70
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
4 years of experience
Waterfront, Cedarburg, WI, 53012

Amanda did an outstanding job taking care of our cats and home while we were away. She has amazing attention to detail, and always gave us plenty of updates and pics so we felt connected to our pets. She is very kind, responsible, and professional. We highly recommend Amanda!

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Michelle S.
Sitter Profile Image: Kylee C.
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Kylee C.
from
$45
per night
5.0 out of 5 stars
3 reviews
1 repeat client
6 years of experience
Grafton, WI, 53024

About: I don’t have much formal dog sitting experience yet, but I’m a college student looking to earn some extra income on the side. I’ve had two dogs of my own for the past six years, so I’m very comfortable with routines, feeding schedules, walks, and understanding dog behavior. I’m flexible with hours, patient, and will make sure your dog feels safe, cared for, and loved. I’m transitioning out of my full-time job to focus on school this summer, which gives me a very flexible schedule. I’m available for overnight stays anytime and can accommodate walks, drop-ins, and check-ins throughout the day. Pet care fits easily into my routine, allowing me to give your dog consistent attention, care, and companionship. I care for pets by following a consistent routine, just like I do with my own dogs. I make sure they’re fed on schedule, get regular walks, playtime, and plenty of attention throughout the day. I’m very attentive to their behavior and needs, whether that’s giving them space, exercise, or extra comfort. I also keep spaces clean and organized. My goal is to make every pet feel safe, comfortable, and cared for the same way I treat my own dogs.

Sitter Profile Image: Isabella A.
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Isabella A.
from
$30
per night
5.0 out of 5 stars
2 reviews
1 repeat client
1 year of experience
West Bend, WI, 53095

Isabella was wonderful with our pets and home! We needed someone quickly for a holiday weekend and she was able to do a meet and greet and take on the days on right away. We got lots of pictures and check-ins and all of our pets were well cared for. Would definitely book again!

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Bailey A.
Sitter Profile Image: Leah A.
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Leah A.
from
$60
per night
5.0 out of 5 stars
2 reviews
2 repeat clients
20 years of experience
Fredonia, WI, 53021

About: I grew up on a farm in Wisconsin, so I’ve had a lot of experience with many different animals; cats, dogs, pigs, goats; you name it! Having just returned from an extended stay in Spain, I’m looking forward to helping families out with their fur babies. I currently live on an 11 acre, unfenced, property and am able to take in a dog or two for a few days. I’m currently working about 30 hours a week 2 minutes from my home. I may look for additional hours as a server, but for now I work 7-2:30 M-F I am able to do drop-ins or stay the night; however, I prefer to not spend the night. I can also keep a dog or two overnight at my house.

Sitter Profile Image: Ju E.
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Ju E.
from
$73
per night
5.0 out of 5 stars
56 reviews
11 repeat clients
45 years of experience
Port Washington, WI, 53074

Ju is amazing with our dogs and has always put us at ease while away knowing our babies are well taken care of, not to mention house sitting.

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Nick B.
Sitter Profile Image: EmmaLee G.
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EmmaLee G.
from
$31
per night
5.0 out of 5 stars
1 review
8 years of experience
West Bend, WI, 53095

About: I currently work at Hightest kennels part time. I’ve also fostered 14 dogs/puppies for Hightest kennels. I am very good at taking care of dogs at all ages. I also follow your instructions very well. I have taken care of puppies, dogs with disabilities and, senior dogs. I have potted trained many dogs and have been successful every time. I am very patient with animals. I am also going to school to become a veterinary assistant. I am currently working part-time at Hightest kennels I would be able to work after Hightest and on my days off. I usually work 2-3 days a week. I will fit pet care in whenever I am not at work. At my home I have two labs that love being around other animals. I have a fenced in area for my dogs to give them time outside. In a client’s home I want to know if your dog has a routine and keep your pet on their routine. I take my pets out many times a day if they are not in their fenced in area. I can also create my dogs if wanted.

Sitter Profile Image: Ella S.
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Ella S.
from
$40
per night
6 years of experience
West Bend, WI, 53090

About: I've taken care of animals my entire life. I've always had dogs, cats, reptiles, small animals, you name it! I have been picking up gigs dog/cat sitting since I was 12. My family, friends, and neighbors have had my help and continue to use me as their first option when help is needed! I'd love to get to know your furry friend :) I currently work part-time from 5pm-10pm Monday thru Friday for the summer, so I am available to spend the morning and midday's playing, feeding, walking, and watching your pet! I have 2 dogs (large and small) and 4 cats of my own. With this, I won't offer in home care due to the stress this can cause your pet. However, I am comfortable with leashing, caging, giving meds, scooping liter pans, and all other responsibilities that come with pet care!

Sitter Profile Image: Grace B.
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Grace B.
from
$50
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
5 years of experience
West Bend, WI, 53095

Grace is 100% reliable and great at communication. My pups adore her and she adores them back. Recently completed a 10 day business trip out of the country and she was amazing. Highly recommend d.

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Lila A.
Sitter Profile Image: Courtney Z.
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Courtney Z.
from
$50
per night
4.9 out of 5 stars
10 reviews
1 repeat client
8 years of experience
Hartford, WI, 53027

Courtney was very sweet and responded quickly to messages. There was a misunderstanding with her work schedule that she would not be in the home for 11 hours. I assumed she would come at lunch to let them out. Never assume - had to call neighbor to let dogs out 2 days as I did not want my dogs left that long without a potty break. Otherwise, all was good.

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Cindy L.
Sitter Profile Image: Emma B.
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Emma B.
from
$60
per night
5.0 out of 5 stars
16 reviews
5 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: Gina P.
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Gina P.
from
$50
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Fredonia, WI, 53021

About: As I said in my headline, I work from home so it is easy for me to pack my stuff up and come care for your pets while you are away. If they will be staying with me they will get spoiled with attention all day. Our backyard is not fenced in but we have a line off our back door from when we had a dog for when nature calls. I am also freely able to let them out for potty breaks while working. My work schedule is very flexible to take your pets for walks or stop in. I currently watch my friends animals when they are away. One household is 2 dogs and 2 cats and the other is just a cat. One of the dogs I have experience administering medication with and dealing with a anxious dog. I also frequently watch a families Boxer when they have errands to run or want to go out for the evening.

Sitter Profile Image: Ellie A.
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Ellie A.
from
$45
per night
5.0 out of 5 stars
2 reviews
3 repeat clients
6 years of experience
Jackson, WI, 53037

About: Hi, I’m Ellie! A little about me, I grew up surrounded by all kinds of animals from cats and dogs to birds and snakes! And I’ve loved going above and beyond to care for them, for as long as I can remember. I have a 10 year old pup myself (Toby) that has helped me understand the dedication and commitment required when caring for pet; especially during a time that might be a bit difficult or confusing for them. I’ve also learned that each pet has their own personality and I will adapt my care to be able to provide exactly what your pet needs. In addition to pet care, I’ll also be able to provide other house sitting needs such as watering plants, gathering mail or anything else that may be needed.

Sitter Profile Image: Larissa M.
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Larissa M.
from
$80
per night
5.0 out of 5 stars
5 reviews
4 repeat clients
10 years of experience
Murray Hill, Grafton, WI, 53024

Larissa was great! We had some last minute schedule changes and she was super accommodating. The dogs loved her and she took great care of our home. We would definitely book Larissa again!

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Emily P.
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The median cost per night for house sitting in Cheeseville is $50

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  • 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.

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

How Rover works

  1. 1. Search

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Sitters in Cheeseville average 4
repeat house sitting clients

FAQs for House Sitting - Cheeseville

Frequently asked questions about Rover

As of June 2026, there are 1,083 sitters on Rover offering House Sitting across Cheeseville. 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 Cheeseville 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 Cheeseville 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 Cheeseville 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 Cheeseville. On Rover:

  • 91% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 99% 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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