Doggy Day Care In Hillside

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Top rated Hillside doggy day care sitters

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: Kim S.
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Kim S.
Star Sitter
from
$32
per day
5.0 out of 5 stars
153 reviews
42 repeat clients
30 years of experience
Glendale, WI, 53217

Thank you so much to Kim! Kim was a fantastic dog sitter for our dog Mushi today. She's very friendly and made us feel very comfortable about leaving our lab mix rescue with her while we enjoyed the Milwaukee Zoo. She walked Mushi and also gave us updates as well as pictures. I highly recommend her to watch your dog.

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Angela S.
Sitter Profile Image: Jessica K.
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Jessica K.
Star Sitter
from
$30
per day
5.0 out of 5 stars
40 reviews
11 repeat clients
15 years of experience
Northpoint, Milwaukee, WI, 53211

Mickey loved his afternoon with Jessica! She took him for walks and made him feel at home. He was relaxed and happy when I picked him up. Jessica is such a kind soul, we feel extemely fortunate to have found her!

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Sally K.
Sitter Profile Image: Esther J.
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Esther J.
from
$27
per day
5.0 out of 5 stars
5 reviews
1 repeat client
20 years of experience
Franklin Heights, Milwaukee, WI, 53206

About: Hi there! We are lifelong dog lover with years of hands-on experience and two sweet pit bulls of my own. Our home is shared with my playful and loving 3-year-old boy and my silly, affectionate 1-year-old girl, who both love making new friends. We've spent many years in responsible dog breeding, which has given me a deep understanding of canine behavior, health, socialization, and individual needs. Whether your pup is shy, energetic, or somewhere in between, We are confident and comfortable caring for all personalities, ages, and breeds. With me, your pets will be treated like part of the family — plenty of love, attention, structure, and fun. I’m committed to creating a safe, positive environment where every dog feels at home. I can’t wait to meet your furry family member! --- If you want, I can also tailor it to a specific service (boarding, drop-ins, walks, etc.) or adjust the tone to be more professional, playful, or concise. I offer flexible scheduling for pet boarding thanks to my role with a property management company, which allows me to be home often and adjust my availability as needed. This flexibility helps me give your pet plenty of attention, supervision, and consistent care throughout their stay. For everyone’s safety and comfort, we kindly require all pets to have their own crate during their stay. Crates provide a secure, familiar space for your dog to rest and relax, especially during downtime or when we briefly step out. Their safety and well-being are always our top priority. Also provide your pet with their favorite food/treats for their stay. We are also able to provide that for an additional fee.

Sitter Profile Image: Hannah N.
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Hannah N.
Star Sitter
from
$40
per day
5.0 out of 5 stars
11 reviews
4 repeat clients
15 years of experience
Historic Third Ward, Milwaukee, WI, 53202

Amanda was super nice with my Kiwi! I could tell kiw had a good time!

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Aleka O.
Sitter Profile Image: Alexandrea S.
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Alexandrea S.
Star Sitter
from
$30
per day
5.0 out of 5 stars
29 reviews
13 repeat clients
4 years of experience
Bay View, Milwaukee, WI, 53207

Alexandrea took great care of my 12 week old puppy Driggs. 😊 She sent me lots of photos of Driggs and kept me updated on how he was doing. She also watched him back to back last minute and I appreciated her willingness to do so! I will definitely be using her again and totally recommend her!

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Marissa T.
Sitter Profile Image: Amy D.
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Amy D.
from
$50
per day
5.0 out of 5 stars
3 reviews
10 years of experience
Lower East Side, Milwaukee, WI, 53202

Amy was great with my pup. She took time with us for meet and greet which was reassuring and helpful. Stayed in touch and sent pics while my pup was with her—highly reccomend.

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Jude S.
Sitter Profile Image: Emily E.
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Emily E.
from
$30
per day
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Northpoint, Milwaukee, WI, 53202

About: I have lifelong experience with animals, having pets all my life and working various animal care jobs. I worked at a doggy daycare for two years in high school, where I gained hands-on experience managing dogs of all sizes, temperaments, and energy levels. That role helped me become confident in reading dog behavior, maintaining safe play environments, and providing attentive care throughout the day. Growing up, my family fostered puppies frequently, so I’m comfortable with young dogs and understand the patience, structure, and consistency they need. I’ve also had dogs and cats my entire life and have pet-sat for neighbors and family friends for years, caring for both energetic pets and older animals who need a gentler, more attentive approach. I recently graduated from UW–Madison and moved away from home, and I truly miss being around animals. Pet sitting isn’t just a job for me—it's something I genuinely enjoy and look forward to. I’m very caring, responsible, and dedicated, and I treat every pet as if they were my own. Your pet’s safety, comfort, and happiness will always be my top priority. Pet care fits very naturally into my routine. I currently work part-time and have a flexible schedule, which allows me to plan my days around the pets I’m caring for. I often work from home, so I’m able to provide consistent supervision, attention, and companionship throughout the day. I’m typically not away from home for more than four to six hours at a time, and I’m intentional about making sure pets get regular care, playtime, and affection. Because of my flexible schedule, I can adapt to your pet’s specific needs—whether that’s extra exercise, medication timing, or just lots of cuddles and company.

Sitter Profile Image: Monica M.
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Monica M.
from
$45
per day
5.0 out of 5 stars
162 reviews
62 repeat clients
16 years of experience
Lower East Side, Milwaukee, WI, 53202

Monica was great! She sent me updates and took very good care of my dog :) my dog is a nervous and anxious girl, but I felt comfortable leaving her with Monica! I will be using her regularly!

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Jasmin E.
Sitter Profile Image: Nylia G.
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Nylia G.
from
$29
per day
5.0 out of 5 stars
3 reviews
8 years of experience
Cold Spring Park, Milwaukee, WI, 53208

About: All my life animals have been a part of my life! I have always had a dog or cat in the home growing up. I just love spending time with my dog, taking him on walks, cuddling with him, and playing fetch with him! Same with my kitten she can be the biggest cuddle bug, or Ms. Independent (I love her either way)! I am currently exploring pet care as a full time job! I have open/available for all your pet care needs day/evening care, boarding, walks! Let’s communicate, I’d love to help you with your pet care needs Currently I have 1 dog a 13 year old chihuahua, and a 6 month old kitten. scrappy and Anastasia are very friendly, and get along great with other animals! We take walks daily, and visit a local dog park 2 to 3 times a week.

Sitter Profile Image: Ixzel R.
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Ixzel R.
from
$35
per day
7 years of experience
Lower East Side, Milwaukee, WI, 53202

About: What sets me apart is both my personal and professional experience caring for animals of all ages, sizes, and personalities. I’ve grown up around dogs my entire life and currently work at Dogtopia, where I care for and supervise dogs daily. This has helped me become patient, attentive, and comfortable working with different temperaments and energy levels. I also have experience with both senior dogs and puppies. My senior dog, Otis, had arthritis, so I learned how important patience, comfort, and attentive care are for older pets. I also helped raise and train our pug puppy with basic training, routines, and socialization. Because of these experiences, I understand that every pet has different needs depending on their age and personality, and I always try to make pets feel safe, active, and cared for like they’re my own.⭐️😊 Pet care is already a big part of my daily routine. I work at Dogtopia, where I help maintain a safe, clean, and fun environment for dogs of all sizes and personalities. 🐾 My job has taught me the importance of paying close attention to dogs’ behavior, safety, and overall well-being throughout the day. When I’m home, I also spend a lot of time caring for my own dog. I enjoy taking him on long walks by the lake, staying active with him through runs and playtime, and making sure he gets plenty of attention, exercise, and care every day.🦮🏃‍♀️❤️ When caring for pets in my home or a client’s home, I always prioritize safety, comfort, and keeping pets on their normal routine as much as possible. I make sure the environment is clean and secure by checking doors, gates, food, and anything that could be unsafe or easily gotten into by curious pets.🤗 I also pay close attention to each pet’s behavior, energy level, and individual needs to help them feel comfortable and stress-free while their owner is away. Whether it’s feeding, walks, playtime, medication reminders, or simply giving them attention and companionship, I always try to make pets feel safe, cared for, and at home.

Sitter Profile Image: Sheila L.
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Sheila L.
from
$30
per day
5.0 out of 5 stars
7 reviews
1 repeat client
40 years of experience
Murray Hill, Milwaukee, WI, 53211

About: I’ve had dogs all my life. I grew up with 6 other siblings and we always had animals around. I lost our beloved family dog about two years ago and I do not want to commit to raising another one since I like to travel. But on my down time, I am willing to walk your dog, spend time with them, and love them up as much as possible. I just recently got an apartment in Milwaukee to be closer to my family so I am looking for something to do and to help out an owner who may need it. I recently retired so I have a lot of flexibility, and a lot more time to spend at home and to care for your dog. It’s just me and my wife that live in the home and she would be available to help if needed. We live in the country on a one acre lot so your dog would have a big area to roam! I can have a pet stay at my house during the day but unfortunately it’s not allowed in my apartment for overnights. If it’s easier to come to your home, I am willing to do that!

Sitter Profile Image: Iuscely F.
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Iuscely F.
from
$38
per day
5.0 out of 5 stars
13 reviews
1 repeat client
10 years of experience
Historic Mitchell Street, Milwaukee, WI, 53204

Luscely was available last minute and didn't make me jump through hoops to dogsit. She was communicative, fair, and my dog was happy. I will absolutely use her again!

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Erin P.
Sitter Profile Image: Melissa A.
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Melissa A.
from
$40
per day
5.0 out of 5 stars
22 reviews
9 repeat clients
12 years of experience
Northpoint, Milwaukee, WI, 53202

About: I had a 12 year old puggle who was my best friend! He was walked every day of his life. Now that he has passed, I am looking to spend time with other furry companions! I am recently retired, so I have lots of time and a very flexible schedule! I love all dogs and am very gentle with all pets. I love downtown and know all kinds of routes for your pets. I am an active person so long or short walks are easy for me to do!

Sitter Profile Image: Mikalanne T.
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Mikalanne T.
from
$40
per day
5.0 out of 5 stars
53 reviews
16 repeat clients
4 years of experience
Riverwest, Milwaukee, WI, 53212

Mika was great! I'm so glad we found them! Very responsive and responsible! I've found it tough to truly find good, communicative, and affordable sitters on Rover. Not anymore! They took the dogs on multiple walks, to the tennis courts, and to get pup cups at the coffee shop. THANKS SO MUCH!

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Tara V.
Sitter Profile Image: Berenice B.
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Berenice B.
from
$40
per day
4.9 out of 5 stars
268 reviews
109 repeat clients
15 years of experience
Bay View, Milwaukee, WI, 53207

Bernice is great! I’d recommend her to anyone. My dogs love going there. She provides great communication and has been flexible when things come up.

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J D.
Sitter Profile Image: Daniel & Holly L.
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Daniel & Holly L.
from
$34
per day
4.9 out of 5 stars
482 reviews
197 repeat clients
45 years of experience
West Allis, WI, 53219

I will always bring my fur kiddo to Dan and holly if they’re available! The made me feel so comfortable! This was my 2nd time using them and I never felt more relaxed with them having my boy!

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Trina B.
Sitter Profile Image: Michelle M.
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Michelle M.
Star Sitter
from
$35
per day
5.0 out of 5 stars
64 reviews
26 repeat clients
15 years of experience
Washington Heights, Milwaukee, WI, 53208

My partner and I wanted to spend a couple of hours on my birthday at some places that don't allow pups - after quick and easy communication with Michelle, we booked daycare with her. Our pup is very social with dogs and people but is always super cautious at first. When we dropped Navi off, she was a bit skittish and didn't really want to go in the house. This left us feeling a bit worried. However, Michelle immediately sent us an update with pictures after we drove away showing Navi explore the house and the backyard. Throughout the day I received so many pictures and videos of Navi playing in the pool and with other pups. It genuinely was the best birthday present I could have asked for. It made us so happy to receive so many updates showing Navi living her best life with her new friends. It was clear Michelle loves doing what she does and cares for every pup like they are her own. If we are ever in the Milwaukee area again, we would love to have you watch after our girl again! Thank you again, Michelle!

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Veni V.
Sitter Profile Image: Michael J K.
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Michael J K.
Star Sitter
from
$25
per day
4.9 out of 5 stars
199 reviews
102 repeat clients
30 years of experience
Grasslyn Manor, Milwaukee, WI, 53216

MJ was amazing with Bobo and warmed up to him in such a short amount of time (usually it takes a while and even days!) He knew how to read Bobo and knew exactly how to interact with him. Definitely will be seeking out MJ to look after Bobo many more times.

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Calvin E.
Sitter Profile Image: Sara M.
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Sara M.
from
$29
per day
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Bay View, Milwaukee, WI, 53207

About: Welcome to my profile! I grew up with a wide variety of pets, so I truly understand how each one has their own unique personality. I know how deserving of love every animal is, and I will do everything in my power to make your pets happy. I treat your pets as my own, while also understanding the need to accommodate to every pet's individual quirks and needs. I recently lost one of my pups to cancer, and because of this, I am really yearning for some more furry friends to meet. Maybe your pet can be my next friend! I recently lost my job, so I currently have a very open schedule! I do have a couple of established clients outside of Rover, but my schedule is still very flexible. I live in a condo-style apartment, so although I do not have a yard, I go on many walks each day- whether around my neighborhood or by driving to a park or beach. I also live just down the street from a dog park, for pups who enjoy socialization and time off-leash. Additionally, I have a patio space for pups who enjoy hanging out al fresco when the weather allows. My own pup is a bit of an escape artist, so I am extra careful with doors, gates, and secure leashing practices. I am also aware of how curious dogs can be, so in my home you can be sure of a safe environment where there are no dangers within a dog's reach (or jump). Not only do I treat your pets with love and respect, but I treat your home with the same care. You can be sure I will keep things neat and tidy, and always make an effort to leave a space cleaner than I found it. No matter the service or location, every animal deserves to feel safe, cared for, and loved. I assure you that I put all my energy into caring for your pets, and I will always treat them as I do my own.

Sitter Profile Image: Meghan S.
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Meghan S.
from
$40
per day
1 repeat client
10 years of experience
Yankee Hill, Milwaukee, WI, 53202

About: I am very reliable and kind. I have experience with all sizes and ages of dogs and cats. My goal is the health and care of your pet. I am a very active person so I enjoy going on runs and walks daily. I think it would be beneficial to dog owners to have me as their dog walker. I make sure the pet is fed and has water. I will play and give them as much as attention as possible and make sure they are comfortable.

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Hillside dog parents share their Rover experiences

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5.0 out of 5 stars

Megan and Rick and our Poppy's new friend Regal are wonderful! After an initial meet and greet, Poppy had her first official daycare which she loved, and we already have an overnight stay planned. So glad to have a great family for her to stay with when needed.

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Parks H.
Doggy Day Care
5.0 out of 5 stars

Dora comes home happy, tired, and level every visit! She is excited to see her friends, and Kristine is very communicative and easy to work with. Thank you from both me and Dora!!

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John B.
Doggy Day Care
5.0 out of 5 stars

Amy was great with my pup. She took time with us for meet and greet which was reassuring and helpful. Stayed in touch and sent pics while my pup was with her—highly reccomend.

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Jude S.
Doggy Day Care
5.0 out of 5 stars

I have a 9 week old puppy and Jessica did a great job with Skye was super happy at drop off and pick up. Great environment for her.

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Adam G.
Doggy Day Care
5.0 out of 5 stars

Benjamin was fantastic for our Charlie girl! Generous and kind, he took time out of a busy Sunday so we could attend a Brewers game while visiting Milwaukee. Charlie instantly loved him which immediately put us at ease. A high-energy “Velcro” dog demanding even more cuddles than exercise, Charlie can be a handful but Benjamin was a perfect fit. Great communication too. We highly recommend him!!

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Paul L.
Doggy Day Care
5.0 out of 5 stars

Monica was great! She made herself available relatively last minute and was very responsive and communicative. And she sent plenty of great photos of our furry boy :)

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Gwyn P.
Doggy Day Care
5.0 out of 5 stars

Ellie is the best! She takes such great care of our 1yr old golden retriever you can really tell she’s such a dog lover. We will continue to use Ellie whenever we need some Rover help.

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James P.
Doggy Day Care
5.0 out of 5 stars

Samantha was amazing my new dog Sharkboy! She took a pretty last minute booking with a meet and greet and all went well and she took him in for basically an entire Saturday. She sent pictures of them having fun and really took great care of him as he's coming out of his shell more and more. Her dog V and her cats are also super friendly and welcoming! Would highly recommend!

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Kumar S.
Doggy Day Care
5.0 out of 5 stars

Genesis takes AMAZING care of my dogs! They love her so much! 🥰 I highly recommend her for all your pet needs! 🐾

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Alexa F.
Doggy Day Care
5.0 out of 5 stars

Jacob and Bridget were AMAZING! Our pup took to them right away and had a blast while there. Exceptional care 👍🏻

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Ivy B.
Doggy Day Care
5.0 out of 5 stars

Kiara had a fabulous time playing with Sonny, and Megan was great with her and a pleasure to communicate with.

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Kristin S.
Doggy Day Care
5.0 out of 5 stars

Luscely took great care our Parchi. Parchi was relaxed when we picked her up. Luscely is an excellent communicator as well and provided us with great updates. I highly recommended using her to take care of your pet.

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Evan K.
Doggy Day Care
5.0 out of 5 stars

Brianna is absolutely amazing. She's super understanding and caring and went above and beyond to talk to me before the trip. My very nervous boy took to her right away and she was so good with updates. I would book her again in a heartbeat!!

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Lauren
Doggy Day Care
5.0 out of 5 stars

Naomi is great. I took a chance given she is new on Rover as she just moved to Milw. she was accommodating to set up a meet and greet a couple days before I needed day care for my pup. what is attentive and listened about my dog. Communicated and sent pictures throughout his day with her. My pup was well cared for and really liked her! sometimes it’s hard when there’s not a lot of reviews, but I am glad I took a chance and I highly recommend Naomi! THANK YOU NAOMI!

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Jude S.
Doggy Day Care
5.0 out of 5 stars

Took great care of our dog Lula! Sent updates and pictures! 😊 Definitely recommend and will use again!

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Alexa F.
Doggy Day Care
5.0 out of 5 stars

This young lady was amazing, very kind and polite. She provided pics of there park trip and I couldn’t be happier with her service!!! Highly recommend

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Cruza D.
Doggy Day Care
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The median cost per day for doggy day care in Hillside is $35

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Sitters in Hillside average 4
repeat doggy day care clients

Doggy Day Care FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Hillside on Rover as of Jun 2026 was about $35 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Hillside doggy day care sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 559 sitters provided doggy day care in Hillside. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 88% of Hillside sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Hillside have an average of 22 years of experience. Sitters offering doggy day care with repeat customers have an average of 4 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Hillside.

Hillside doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Hillside sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:

  • Puppies and high-energy dogs
  • Dogs with special needs, including seniors
  • Pet parents who work long hours
  • Dogs with separation anxiety

There are 559 sitters offering doggy day care in Hillside on Rover, so you’re sure to find the perfect match for your dog! In Hillside, 83% of sitters offer daily exercise, 98% offer medication administration, and 98% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect doggy day care sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your doggy day care sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 doggy day care 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 doggy day care service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.