House Sitting Ashippun

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Ashippun, 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: Kendra M.
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Kendra M.
from
$45
per night
5.0 out of 5 stars
13 reviews
2 repeat clients
3 years of experience
Oconomowoc, WI, 53066

Kendra was amazing with my dog Winter! She was a great house guest and cleaned up after herself and beyond. I got several pictures of Winter and prompt replies when I would check in. I will definitely use her every time I need someone to come stay.

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Stephanie J.
Sitter Profile Image: Tara R.
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Tara R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
83 reviews
18 repeat clients
20 years of experience
Delafield, WI, 53018

Tara was fabulous - Hutch was very spoiled with multiple daily walks and I got lots of pictures and updates. He barely acted like we’d been gone!

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Lisa W.
Sitter Profile Image: Alex M.
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Alex M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
48 reviews
16 repeat clients
10 years of experience
Oconomowoc, WI, 53066

Loved Alex so much! I have an anxious little lady and the minute Alex walked in Soph laid on the floor and wanted tummy rubs. She had a very calming presence which was so comforting knowing she would be in good hands. She was so easy to communicate with and kept us updated while we were gone. Would love to use her again ❤️

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Maria B.
Sitter Profile Image: Katelyn W.
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Katelyn W.
Star Sitter
from
$60
per night
4.8 out of 5 stars
34 reviews
16 repeat clients
8 years of experience
Oconomowoc, WI, 53066

Have used Kate multiple times to stay with our pets and our house. She does a great job and is super respectful of the space. Will continue to use her in the future.

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James F.
Sitter Profile Image: Isabella R.
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Isabella R.
from
$37
per night
5.0 out of 5 stars
5 reviews
15 years of experience
Neosho, WI, 53059

Izzy was great! She stayed in touch and made sure my puppy was well taken care of.

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Austin S.
Sitter Profile Image: Jade B.
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Jade B.
from
$60
per night
10 years of experience
Oconomowoc, WI, 53066

About: I’m a disabled veteran & dogs have always been my peace so i decided to start incorporating more of them into my daily life & call it “work” 🥰 pet-loving is part of my every day life! i take my own pups for walks in the morning before the heat, and during the warmest days of winter. i love being outside, playing with animals & taking care of them! i will use the app, frequent communications in texting, etc. along with pictures and videos to send to all my pet parents! walking the pups at least a mile, if they can, or more if requested! i also walk all my clients separately from others, so no need to worry about differing personalities.

Sitter Profile Image: Megan B.
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Megan B.
from
$60
per night
5.0 out of 5 stars
19 reviews
1 repeat client
20 years of experience
Watertown, WI, 53094

We had Megan house sit for us for about 5 days. Our dog loved her and she took really good care of him and his puppy energy. She also watered the garden, fed our guinea pig, and left our house spotless. Communication with her wasn't an issue. For our In person meet and greet she used an app with a translator (went real smoothly) and while we were away she was great about texting us updates. Next time we need a house sitter she'll be the first person I reach out to!

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Tiegan P.
Sitter Profile Image: Taylor S.
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Taylor S.
from
$50
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
25 years of experience
Delafield, WI, 53018

My experience in working with Taylor was excellent. Great communicator and most importantly cared for my 10yr lab while out in a work trip. Taylor went above and beyond what was required as she left the house spotless, and washed bedding and bathroom towels before leaving.

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Todd L.
Sitter Profile Image: Bella B.
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Bella B.
from
$63
per night
5.0 out of 5 stars
35 reviews
18 repeat clients
15 years of experience
Watertown, WI, 53094

It was so nice to have Bella cat/house sit for us on our recent trip. So comforting to know our cats had a person to spend time with in the evenings and give them lots of attention. She also left our place super clean! Would definitely ask back. Thanks Bella!

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Kelly S.
Sitter Profile Image: Yasmin U.
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Yasmin U.
from
$75
per night
5.0 out of 5 stars
2 reviews
4 years of experience
Watertown, WI, 53094

About: With years of hands-on experience caring for both dogs and cats, I bring a well-rounded and deeply committed approach to pet care. I am the owner of Oh My Paws, a pet-sitting business I started during college, and have worked as a kennel technician, dog handler for Can Do Canines, and am currently completing an apprenticeship at a Humane Society. These roles have given me experience with a variety of temperaments, medical needs, and behavioral challenges. What truly sets me apart is my background in dog behavior and training. I am currently studying to earn my CPDT-KA (Certified Professional Dog Trainer – Knowledge Assessed) certification and have experience training service dogs through the Falcon Fetch program. This gives me a unique ability to understand body language, reduce stress in pets, and ensure a safe, enriching environment during their care. Pet care is a central part of my life and something I prioritize in my weekly routine. I have very open availability on weekends (Saturday–Sunday), and I’m also available on Mondays if needed. This flexibility allows me to provide consistent and dependable care, whether it’s for daily visits, overnights, or last-minute bookings. Because I run my own pet-sitting business and am actively involved in training and animal welfare work, I structure my schedule around the pets I care for. I take the time to provide each animal with individualized attention, exercise, enrichment, and a calm, safe environment. Whether caring for pets in my home or in a client’s home, safety and trust are always my top priorities. I begin with a detailed intake to learn about each pet’s routine, medical needs, triggers, and preferences, and I tailor my care accordingly. I use positive reinforcement and clear communication to build trust with animals, helping them feel safe and comfortable. In a client’s home, I maintain their pet’s usual routines as closely as possible to reduce stress. I’m respectful of the home environment, leave things exactly as I found them, and provide regular updates with photos and notes for peace of mind.

Sitter Profile Image: vtheine@gmail.com T.
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vtheine@gmail.com T.
from
$42
per night
5.0 out of 5 stars
33 reviews
9 repeat clients
50 years of experience
Oconomowoc, WI, 53066

Murphy Loved Vonnie! And she sent pictures. She's amazing! I will definitely be reaching out to her again. Best Sitter Ever. Totally made me feel comfortable leaving my best buddy with her. She is AWESOME!

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Patrick P.
Sitter Profile Image: Noah B.
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Noah B.
from
$28
per night
15 years of experience
Ixonia, WI, 53036

About: I've cared for puppies and senior dogs alike. I've been taking care of dogs my entire life and I am familiar with all breeds. From Daschund to German Shepherd I have been with them all. I currently even own a very well trained Dachshund and shes almost 2 I'm available most everyday rain or shine. I am very attentive and capable of taking care of most any dog. I always take the necessary time to care for a dog as they need it and when they need it I don't offer this service, but I am willing to take care of your pets in your home at any time that you may need it.

Sitter Profile Image: Meghan A.
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Meghan A.
from
$60
per night
5.0 out of 5 stars
34 reviews
9 repeat clients
20 years of experience
Rubicon, WI, 53078

Meghan was wonderful! She put up with our naughty little dog and two pups. She kept us up to date and was very informative. We will be using her again! Wonderful.

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Michele V.
Sitter Profile Image: Cindy S.
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Cindy S.
from
$55
per night
5.0 out of 5 stars
51 reviews
15 repeat clients
45 years of experience
Oconomowoc, WI, 53066

Cindy Is the ideal cat sitter. I wanted to not have to worry about Baby Bear having a clean litter box and eating his wet and dry food. Cindy was there for him and he’s happy! That’s what a great pet sitter does.

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Larry B.
Sitter Profile Image: Brenna C.
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Brenna C.
from
$50
per night
5.0 out of 5 stars
4 reviews
17 years of experience
Summit, WI, 53066

Brenna is amazing! Loved getting updates & communicating with her. Our dog had an amazing time with her & we felt so comfortable leaving him in her hands. We’re lucky we found her!

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Abbey S.
Sitter Profile Image: Ramsey S.
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Ramsey S.
Star Sitter
from
$85
per night
5.0 out of 5 stars
54 reviews
12 repeat clients
40 years of experience
Oconomowoc, WI, 53066

Ramsey did an excellent job taking care of my two labs. I enjoyed regular pictures and updates on what they were doing. They were obviously loved; and very happy campers upon my return from a short trip. I felt confident in having Ramsey stay in my home, and really glad the dogs could keep their regular routine.

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Katie Q.
Sitter Profile Image: Molly M.
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Molly M.
from
$75
per night
5.0 out of 5 stars
16 reviews
5 repeat clients
18 years of experience
Oconomowoc, WI, 53066

About: I grew up with dogs and have taken care of friends and families pets my whole adult life. I also have a dog of my own! I’m comfortable with dogs of all sizes and breeds and am reliable and comfortable walking, feeding, and providing all general cares! I work full time, day time hours, but mostly from home. I take care of my own pup during the day, we go on walks during my breaks and lunch. I’m available to walk or watch pets during the day, in the evenings/nights or on weekends! I have a golden retriever at home to keep your pet company ! He loves friends and making new ones! Close by walking paths and fields to walk, as well as a dog park on site if wanted.

Sitter Profile Image: Raegan S.
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Raegan S.
from
$55
per night
5.0 out of 5 stars
2 reviews
9 years of experience
Oconomowoc, WI, 53066

Reagan was awesome with my animals. She sent pictures and communicated with me throughout the stay and before. My animals were happy and wonderfully cared for. She is kind and gentle and patient with my youngest pup who is still very puppy and hyper.

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Taylor M.
Sitter Profile Image: Brooke G.
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Brooke G.
Star Sitter
from
$90
per night
5.0 out of 5 stars
36 reviews
3 repeat clients
20 years of experience
Oconomowoc, WI, 53066

About: We recently moved back to our roots to a spot right off South St. In Oconomowoc. We had our dog sitting business in San Diego, CA and will miss our furry friends so much! My husband and I both love animals very much and have the perfect set-up to host. We enjoy morning and evening cuddles and allow dogs on the couch and bed :) We will take care of your pup just the same as we care for our own. We have a 4 year old mutt that we adopted 3 years ago who has brought so much joy to our life! She loves to play and enjoys the dog park/hanging around other dogs as much as she can. She loves walks around the lake as I am sure your pup will too! We both have experience taking care of other dogs and have dog sit for many of our friends and family members for extended periods of time when they are out of town. We can provide pictures as little or as often as you would like. Excited to meet your furry friend soon! I currently work 4 days of the week and have every Thursday off. My husband works remotely from home so he is able to tend to your pups needs all day. This schedule works great for our pups that need frequent potty breaks and attention. We have long leashes attached to our back deck so the dogs can enjoy the sun and being outdoors as much or as little as they would like without having to worry about them wandering off! Moxie loves basking in the sun and shade out there as I am sure yours would too! Water bowls always provided and refreshed as needed.

Sitter Profile Image: Allison S.
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Allison S.
Star Sitter
from
$88
per night
5.0 out of 5 stars
56 reviews
21 repeat clients
3 years of experience
Sussex, WI, 53089

Allison took wonderful care of our fur babies (and our home). We appreciated the frequent pictures/videos, since we missed our boys something terribly. Our cats are usually scaredy cats, and hide from strangers. Allison bonded with them quickly and they were comfortable with her around. One of our cats require daily medication, and Allison was such a pro, making sure he was well cared for. We truly appreciate her care and support of our family and home. Would highly recommend.

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Thomas D.
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The median cost per night for house sitting in Ashippun is $50

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

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Popular requests for house sitting - Ashippun

Select a filter and find qualifying sitters offering house sitting.

Sitters in Ashippun average 4
repeat house sitting clients

FAQs for House Sitting - Ashippun

Frequently asked questions about Rover

As of September 2026, there are 971 sitters on Rover offering House Sitting across Ashippun. 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 Ashippun 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 Ashippun 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 Ashippun 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 Ashippun. On Rover:

  • 91% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 97% 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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