House Sitting in Ashippun

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Top rated Ashippun 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: Tara R.
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Tara R.
Star Sitter
from
$52
per night
5.0 out of 5 stars
74 reviews
17 repeat clients
20 years of experience
Delafield, WI, 53018

Tara is exceptional when it comes to watching your fur babies! She watched our dog (Marley) while on vacation for a week. She provided plenty of updates with pictures that helped in knowing Marley was doing well. I would highly recommend Tara if you are in need of a pet sitter.

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Randy S.
Sitter Profile Image: Joey C.
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Joey C.
from
$65
per night
5.0 out of 5 stars
77 reviews
18 repeat clients
40 years of experience
Hartland, WI, 53029

Joey was fantastic. She took our dogs on multiple walks and played with them in the yard. Joey sent us multiple pictures throughout her time with the dogs and gave us updates regularly. We will definitely use her in the future.

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Erin R.
Sitter Profile Image: Victoria K.
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Victoria K.
from
$25
per night
5.0 out of 5 stars
3 reviews
10 years of experience
Oconomowoc, WI, 53066

Victoria did a great job taking care of our dogs. Was also very good at sending photos and communicating. Would definitely recommend!

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Analisia W.
Sitter Profile Image: Kristin C.
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Kristin C.
from
$50
per night
5.0 out of 5 stars
37 reviews
10 repeat clients
10 years of experience
Watertown, WI, 53094

Outstanding communication and treated the dogs like if they were her own. The house was clean and orderly we would definitely love to have her back again.

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Brenda S.
Sitter Profile Image: Allison S.
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Allison S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
53 reviews
20 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.
Sitter Profile Image: Cooper B.
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Cooper B.
from
$70
per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Hartland, WI, 53029

Cooper is a kind, reliable pet sitter. I felt completely comfortable having him spend time with my dogs and stay in my home. I’d definitely work with him again and would encourage you to consider him for your needs as well.

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Ryan P.
Sitter Profile Image: Katelyn W.
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Katelyn W.
from
$60
per night
5.0 out of 5 stars
25 reviews
10 repeat clients
8 years of experience
Oconomowoc, WI, 53066

Katelyn watched my English Bulldog and Chocolate Lab while I was on vacation for several days. She took great care of my fur babies. She fed them, walked them, let them out several times, and gave them loves and pets. She sent good notes and several pictures and videos throughout the stay.

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Danielle R.
Sitter Profile Image: Taylor S.
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Taylor S.
from
$50
per night
5.0 out of 5 stars
7 reviews
3 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: Rowan B.
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Rowan B.
from
$40
per night
5.0 out of 5 stars
3 reviews
20 years of experience
Waukesha, WI, 53188

Our Chunks loved hanging out with Rowan! He got lots of excersize, love, and play time and is now sleeping peacefully because he had so much fun! Definitely will be using her again!

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Naomi N.
Sitter Profile Image: Molly S.
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Molly S.
from
$30
per night
5 years of experience
Oconomowoc, WI, 53066

About: I’ve grown up around dogs and have experience caring for pets in multiple homes. I regularly stay at three different families’ houses when they go out of town, and each family has two dogs that I care for by feeding, walking, playing with, and keeping them company. I also have two dogs of my own, so I’m very comfortable around different personalities and routines. In addition, I help my grandma care for her Rover dogs and have experience helping train my own puppy. I’m dependable, organized, and genuinely love spending time with animals. I currently nanny during the day, but I still have plenty of time for pet care throughout the week. I’m available for drop-in visits with the kiddos during the day, free most evenings and nights, and available on weekends as well. I genuinely enjoy spending time with animals, so pet care fits naturally into my routine and is something I look forward to. I always want pets to feel safe, comfortable, and cared for while their owners are away. I pay close attention to routines, feeding schedules, litter boxes, walks, medications, and any special instructions to make sure each pet gets personalized care. Growing up with three cats and currently having two dogs of my own has made me very comfortable around animals and attentive to their different personalities and needs.

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

Cindy was great! Great communications and took excellent care and attention to my dog while I was away. Valentine got daily walks and play time; the pictures sent to me was very reassuring.

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Merry C.
Sitter Profile Image: Rebekah B.
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Rebekah B.
from
$50
per night
5.0 out of 5 stars
6 reviews
1 repeat client
4 years of experience
Watertown, WI, 53098

Rebekah stayed with our 4 dogs and 1 cat this past weekend and honestly everything went perfect! Our dogs and cat were very well taken care of and our house looked as though she never stayed. She was very prompt with updates throughout the weekend and gave our fur babies so much love! We will be using her again in the future and would highly recommend!!

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Julie G.
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
31 reviews
9 repeat clients
50 years of experience
Oconomowoc, WI, 53066

Vonnie took very good care of all of our fur babies. She contacted us with updates and questions. She also watched our house and everything was nice and clean when we returned. Would definitely use her again and recommend her for your your fur babies.

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Susan K.
Sitter Profile Image: Haydn H.
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Haydn H.
from
$60
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
8 years of experience
Ixonia, WI, 53036

Haydn did a great job with my pup. She spent a ton of time with her playing and taking her on walks. I got updates and pictures throughout the time period. The house was in great shape when I got home and and very clean. I would definately recomment Haydn and use her again!

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Angela N.
Sitter Profile Image: Brenna C.
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Brenna C.
from
$40
per night
17 years of experience
Summit, WI, 53066

About: Hey there! I’ve grown up with dogs and had lots of cats all of my life! I would be happy to help you out with your loved family members! I’m great with drop ins, as well as staying at your house for overnights. I have availability every day, except for Tuesday and Wednesdays. Please let me know if I can be of any assistance with your fur babies! ❤️ Pet care fits into my routine because I only work Tuesday Wednesdays. I don’t mind dropping in to say Hi to pets, let them out, or take them for a walk. I care for your pet as if they were my own💕 pets are part of our family!!!!! I have 3 dogs of my own which mean the world to us!

Sitter Profile Image: Lilianne O.
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Lilianne O.
from
$30
per night
6 years of experience
Watertown, WI, 53098

About: I have a 6 year old golden doodle! Love to be around all my family members dogs as well! I have dog sat a number of times for my neighbors! I’ll be taking online classes throughout the summer, so I’ll be available almost whenever. I will not have any other job so I should have a pretty open schedule. Besides a few trips up north occasionally my weeks are open! I will care for your dogs however you ask you me too! I have a golden doodle at home with my parents, so ideally being at the clients house would work best! I’d love to play with them, walk them, feed them, whatever they need!

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: Meghan A.
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Meghan A.
from
$60
per night
5.0 out of 5 stars
31 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: Elizabeth C.
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Elizabeth C.
from
$40
per night
40 years of experience
Oconomowoc, WI, 53066

About: I have cared for animals my entire life and truly believe they are part of the family. Over the years, I’ve had hands-on experience with many different types of pets, including cats, dogs, birds, horses, chickens, rabbits, guinea pigs, amphibians, and more. Animals are my passion, and caring for them genuinely brings me joy. Whether it’s providing companionship, playtime, feeding, or making sure they feel safe and comfortable while you’re away, I treat every animal with the same love and attention I would give my own pets. You can feel confident knowing your pet will be cared for by someone who is experienced, attentive, and truly loves animals. Pet care fits very naturally into my daily routine, and I prioritize making sure animals receive attentive and reliable care. I am currently available during the day, which allows me to be flexible and attentive to your pet’s needs. On weekdays, I do drop off and pick up my two children from school (ages 8 and 10), but outside of those short times my schedule is very open. This allows me to provide consistent care, visits, playtime, feeding, and companionship for your pets. Because I structure my day around the animals I’m caring for, you can feel confident that your pet will receive dependable attention and thoughtful care while you’re away. I prioritize safety, comfort, and trust when caring for pets, whether they are in my home or their own familiar environment. My home sits on nearly one acre with an unfenced yard, which allows for plenty of outdoor play and exercise. Dogs can enjoy time outside on leash, and off-leash play can be discussed depending on the dog’s training and owner preferences. Inside my home, my own pets have separate spaces, which allows visiting animals to be safely and comfortably separated if needed. This helps ensure a calm and secure environment for everyone. I am also happy to care for pets in their own homes. I am very respectful of clients’ homes and always follow instructions carefully to maintain your pet’s normal routine. Whether in my home or yours, I provide attentive care including feeding, playtime, companionship, exercise, and administering medications if needed. My goal is always to make pets feel safe, comfortable, and well cared for while you are away.

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.

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  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 Ashippun is $50

Why Choose Rover?

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  • 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 Ashippun average 3
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 Ashippun 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 Ashippun 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 327 house sitters in Ashippun. 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, 89% of Ashippun house sitters respond in under an hour.

House sitters in Ashippun have an average of 16 years of experience. House sitters with repeat customers have an average of 3 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 Ashippun.

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. Ashippun 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.