Doggy Day Care Ashippun

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Ashippun, Find top rated doggy day care

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

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Sitter Profile Image: Anne W.
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Anne W.
from
$45
per day
5.0 out of 5 stars
19 reviews
7 repeat clients
5 years of experience
Oconomowoc, WI, 53066

Anne took great care of our dog Sam. We plan on having her take care of him in the future.

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Wendy D.
Sitter Profile Image: Amanda C.
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Amanda C.
from
$25
per day
30 years of experience
Neosho, WI, 53059

About: I have had pets all my life. I have 5 of my own dogs of various shape and size and foster for a couple different rescues! I am very flexible, I'm available most of the time and love to meet new pets. I try to fit the needs of pet owners where I can. I don’t plan on doing any home care. I have 5 dogs of my own and also foster. This just isn’t possible at this time.

Sitter Profile Image: Brooke G.
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Brooke G.
Star Sitter
from
$40
per day
5.0 out of 5 stars
29 reviews
2 repeat clients
20 years of experience
Oconomowoc, WI, 53066

We had a last minute booking that they were able to accommodate. Great communication before and during stay. We loved getting pics and video, too! Boone well loved and comfortable during his stay. Came home a very happy guy.

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Heather L.
Sitter Profile Image: Natalie K.
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Natalie K.
from
$25
per day
5.0 out of 5 stars
7 reviews
2 repeat clients
12 years of experience
Oconomowoc, WI, 53066

About: I have always had a dog growing up, so I learned from a very young age how to care for a pet. Friends and family have trusted me to take care of their dogs since I was around 12 years old. This includes stopping in the house to take them to the bathroom and feeding them, as well as giving medication if needed. Lots of snuggles and playtime too of course! I have taken care of dogs in the client's home for up to a week and cared for them at my home as well. No need to worry about any complex feeding schedules. I can manage it all. I am very comfortable with any age, breed, and sized dog! I have a one-year-old pup, so I am very familiar with training and puppy classes. I have volunteered at the humane society and when I was in high school, I job shadowed at a veterinary clinic. I currently work as a substitute teacher so my schedule is extremely flexible! During the summer months I am completely open. Weekdays and weekends any time of day. I make my own schedule so there will be no conflicts. I have a fenced in backyard with plenty of space for some off leash playtime! My dog loves to run around playing fetch with a ball or stick. I have a walking path across the street from my home and am walking distance to nature hill for some extra exercise. I always have water, waste bags and small treats with me when going on walks. (My dogs personal favorites are cheerios). I am comfortable walking with any leash, collar or harness. I have two kennels in my living room if your dog needs to be crated. At least one crate is big enough to fit a large or XL dog. I have a baby gate in front of my stairs, and the basement door is always shut. I personally love going to the pet store or drive thru to get my pet a pup cup! I would be more than happy to take your dog for an adventure and for some extra love and enrichment!

Sitter Profile Image: Heather B.
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Heather B.
Star Sitter
from
$40
per day
5.0 out of 5 stars
30 reviews
9 repeat clients
35 years of experience
Oconomowoc, WI, 53066

Heather was absolutely wonderful with our little sweet pup. He had a walk, breaks, fun with his ball. Heather was extremely accommodating and flexible. Once you meet her, she outs you at immediate ease. Will happily use her again!

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L W.
Sitter Profile Image: John C.
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John C.
from
$25
per day
5.0 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Oconomowoc, WI, WI, 53066

John did an excellent job of taking care of my Sylvester. And Sylvester was excited to go back!

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Jennifer P.
Sitter Profile Image: Cindy S.
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Cindy S.
from
$45
per day
5.0 out of 5 stars
51 reviews
14 repeat clients
45 years of experience
Oconomowoc, WI, 53066

We had a great experience with Cindy! She was very responsive to me and attentive to Chica. Chica was in no rush to leave. That’s a good sign.

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Sandy L.
Sitter Profile Image: Anna R.
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Anna R.
from
$27
per day
5.0 out of 5 stars
2 reviews
17 years of experience
Rubicon, WI, 53078

About: Hello! I'm Susu and I would love to care for your pet. I've been caring for animals since a very young age. My family and I would always bring in and care for fosters and strays, along with our own. Learning to train pups at such a young age has made it one of my biggest passions. I understand that every dog is different and it's all about learning who they are. I adapt and adjust to any dogs needs until they are happy and comfortable. Of course playtime is great but I will also inforce balance by having them do tricks and giving rewards. I believe in positive reinforcement and encouraging them to be their best furry selves. I will truly love your pet like my own. I do have a dog of my own named lexus. She is a rescue so she can be a little wary of strangers but is never shy around another furry friend! She has been socialized all of her life and loves to run and play. She understands social cues very well so if the other dog is uninterested in playing she will leave them alone. If Lexus and your dog meet I'm sure they will be best of friends! Whether it's just a walk or they stay a few nights I cant wait to meet your pup! My schedule is very flexible. I am a stay at home mom, photographer, mua and an artist. I am open to last minute scheduling if needed or scheduling something further in advance. Something consistent and on going would be preferred but if it’s just a one time thing that is okay with me as well! For walks we will go on a walk around the block. If needed we will work on not pulling the leash. For a boarding visit I will get them all set up and comfortable in my house. If it’s nice out we will go for a walk and play outside. Playing indoors as well and working on tricks they know or maybe learning a new one. Potty breaks will be provided whenever needed and food will be given as directed.

Sitter Profile Image: Mikaela & Shane P.
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Mikaela & Shane P.
Star Sitter
from
$50
per day
5.0 out of 5 stars
35 reviews
14 repeat clients
20 years of experience
Hartland, WI, 53029

Had a great report from Shane & Mikaela! Lots of pictures taken during his daycare day! :)

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Carrie D.
Sitter Profile Image: Molly M.
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Molly M.
from
$45
per day
5.0 out of 5 stars
16 reviews
5 repeat clients
18 years of experience
Oconomowoc, WI, 53066

Molly takes the best care of my pup! She provides updates and gives him so much attention, he always comes home exhausted! She is excellent and I highly recommend for anyone needing boarding or daycare!

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Josh B.
Sitter Profile Image: Kristen D.
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Kristen D.
from
$30
per day
5.0 out of 5 stars
14 reviews
2 repeat clients
40 years of experience
Delafield, WI, 53018

Kristin took great care of Ace the 2 days he stayed there. She tries to make him comfortable even though he was suffering from separation anxiety. She sent photos both days. Thank you.

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Derek N.
Sitter Profile Image: Jill G.
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Jill G.
from
$25
per day
5.0 out of 5 stars
7 reviews
2 repeat clients
28 years of experience
Hartland, WI, 53029

About: I make sure that all dogs in my home feel comfortable and are loved like one of the family. I offer them the same level of attention as my own dog. My dog Bella is looking for a playmate and loves to cuddle up with other dogs and cats. We also have my daughter cat occasionally through out the Summer. We prefer that your dog is no larger than 30 pounds, and that your dog does not shed. I also require that all dogs are crated in our large mudroom when I am not at home and at night. All pets will have access to free roam while being monitored with toys and balls. I do provide a large outdoor area for potty breaks, a nice neighborhood for walks and a golf course in my backyard for running and playing!! I work from home so all the pups are able to have freedom and exercise most days and nights. Both my husband and I work from home so someone is always home. We're up early and take dogs out for playtime, potty, and walks throughout the day. We treat your dog like one of the family. You can trust that he/she will get plenty of love, cuddle time and exercise. Sometimes walks twice a day!

Sitter Profile Image: SueAnn A.
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SueAnn A.
from
$35
per day
5.0 out of 5 stars
4 reviews
2 repeat clients
25 years of experience
Oconomowoc, WI, 53066

Louie had a great time playing all day with SueAnn and her hubby! They took good care of him while we were in the Dells. Thank you again!

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Renee S.
Sitter Profile Image: Roger W.
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Roger W.
from
$35
per day
5.0 out of 5 stars
41 reviews
14 repeat clients
30 years of experience
Hartland, WI, 53029

Roger did a great job taking care of our 5 month old, super high energy Belgian Malinois puppy for about half a day. She was worn out by the time I picked her up which is awesome. And I really appreciate that Roger was able to do this on Mother's Day--many others didn't have that kind of availability. We'll definitely do doggie daycare with Roger the next time we need to. Thanks Roger!

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Erica P.
Sitter Profile Image: Julie E.
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Julie E.
Star Sitter
from
$27
per day
5.0 out of 5 stars
56 reviews
14 repeat clients
40 years of experience
Oconomowoc, WI, 53066

About: I’ve had dogs all my life. I love to walk and play with them and also have snuggle time if they like that. My schedule is flexible to accommodate their needs! I have not done injections but am willing to do if trained I’m retired so I have plenty of time to care for your pet in my home or come to your home for check-ins and walks. I have a fenced yard and am close to a local state park for long walks. I also live in a very walkable subdivision. I don’t mind a well behaved pet on furniture.

Sitter Profile Image: Denise G.
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Denise G.
from
$40
per day
5.0 out of 5 stars
37 reviews
17 repeat clients
25 years of experience
Hartford, WI, 53027

About: I have taken care of my own pets, as well as many others in my home. Friends, family, and neighbors trust me with their loved pets! I am currently working part time and mostly from home. I am in school part time from home as well, so I can be with your pet the entire time. I have a fenced in yard and only 1 dog myself. I can walk dogs. I can crate them if needed. I can offer baths as well!

Sitter Profile Image: Katy & Dennis "DJ" G.
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Katy & Dennis "DJ" G.
Star Sitter
from
$32
per day
5.0 out of 5 stars
120 reviews
39 repeat clients
35 years of experience
Wales, WI, 53183

My dogs had a blast! Wonderful family I will definitely use them again. Great communication

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Cat C.
Sitter Profile Image: Charles & Jessica W.
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Charles & Jessica W.
from
$35
per day
10 years of experience
Hartford, WI, 53027

About: Dogs are a big part of our daily life. We have two of our own—a friendly Golden Retriever, Oakley, and a playful Bernedoodle, Teddy—so I’m very familiar with different energy levels, personalities, and routines. I have hands-on experience with: • Daily walks, playtime, and exercise • Feeding schedules and portion control • Crate routines and basic training consistency • Managing multiple dogs at once • Recognizing behavior changes and keeping dogs comfortable Because I work from home, your dog won’t be left alone for long periods. They’ll get consistent attention, outdoor time, and a structured but relaxed environment. We also have a fenced-in yard, which allows for safe play and movement throughout the day. Our home is set up to be dog-friendly, and I treat every dog like part of the family—while still respecting their routine so they feel secure. Flexible availability for mornings, afternoons, evenings, and weekends depending on scheduling. I work from home and can provide all your pets needs in our home. Calm, dependable, and attentive care Safe family environment with clear expectations Must be good with both children and other dogs Fenced yard for safe outdoor play Experience managing multiple dogs Regular communication and photo updates Focus on routine, safety, and comfort

Sitter Profile Image: Jenifer D.
Verified Background Check
Jenifer D.
Star Sitter
from
$32
per day
5.0 out of 5 stars
375 reviews
160 repeat clients
22 years of experience
Pewaukee, WI, 53072

Just like everyone else, Teddy and I love her! Great home away from home for your fur baby. ? We’ll be coming back over and over again. I’m pretty sure he would’ve been happy to move right in with her permanently ❤️

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Stefanie B.
Sitter Profile Image: Mary & Hanna S.
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Mary & Hanna S.
Star Sitter
from
$40
per day
5.0 out of 5 stars
140 reviews
65 repeat clients
11 years of experience
Sussex, WI, 53089

This was my 1st time leaving my dogs with a sitter I didn't personally know. I was nervous, but they LOVED it! Mary & her family treated them like their own. They were exhausted everyday from playing with the other dogs and seemed excited to go back. I received daily updates & photos when they were there. It allowed me to have fun on my vacation because I knew they were happy! Thank you Mary ❤

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Connie M.
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The median cost per day for doggy day care in Ashippun is $35

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Meet local sitters who will treat your dogs like family

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Popular requests for doggy day care - Ashippun

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Sitters in Ashippun average 5
repeat doggy day care clients

FAQs for Doggy Day Care - Ashippun

Frequently asked questions about Rover

As of August 2026, there are 423 sitters on Rover offering Doggy Day Care across Ashippun. Enter your ZIP code to see which available sitters are closest to your home.

Sitters on Rover can offer flexible scheduling, so you can coordinate times that work best for you and your pet—whether that’s early drop-off or later pick-up to match your Ashippun commute.

If your schedule changes, it’s best to let your sitter know through the app as early as possible. Many sitters can adjust pick-up and drop-off times when needed.

Think of doggy day care as your dog’s fun, supervised play date that happens to fit into your workday. Day care through Rover takes place in a real home. This offers a calmer and more personalized environment for your pup.

A typical day can include companionship, one-on-one attention, and same day pick-up and drop-off. Many sitters can also offer structured routines and exercise throughout the day. For recurring, weekly day care, sitters will include photo updates so you can see your dog in their element.

Here are tips for finding the ideal day care fit for your dog:

  • For some small dogs: In-home day care can be the perfect fit. Look for sitters whose "can host" section only lists dogs weighing 0–7 kilograms and/or 7–18 kilograms. During your Meet & Greet, ask about play areas based on dog size and energy level.
  • For high-energy dogs: The ideal doggy day care can offer scheduled breaks and outdoor spaces or activities. You can also find sitters who host multiple dogs to satisfy your pup’s socializing needs.
  • For dogs who prefer human-only companionship: Use the filters "Doesn't own a dog" and "Only accepts one pet at a time" to find the right care.

Play groups can be an option when you book with a day care sitter through Rover. Many sitters do host a small number of dogs at the same time. Smaller dog packs are generally safer, more fun, and ideal for dogs who enjoy playtime but also want to relax throughout the day. When looking for your dog’s pack, check the sitter’s profile to see if they "Accept multiple clients" or have their own dogs. Then during the Meet & Greet, you can see whether your dog is a good fit for their social circle!

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in WI ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

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 .

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.

A Meet & Greet is a short introductory meeting between you, your dog, 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.

Yes, Rover is well-suited for finding sitters who can care for your pet within 24 hours. With 423 sitters in Ashippun, 83% respond to messages in under an hour.

You can message multiple sitters simultaneously to find the fastest available match. If you need care today or tomorrow, you can look for sitters with a "calendar last updated" notice on their profiles.

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.

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