Doggy Day Care in High Crossing, Madison, WI
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Top rated High Crossing doggy day care sitters

“Emily took great care of our pup, Toby! He is 10 weeks old and she was capable of managing the extra needs of a young puppy. Emily was very communicative and responsive to messages. We would send our pup to be cared for by her again!”


“Cynthia’s pupdates are THE BEST! I look forward to her primo photos & pupdates every time. My pup Popsicle gets so excited when she sees Cynthia. Hands-down the most thoughtful, caring pup-sitter that I have encountered. ✨”


“Briana is such a kind and empathetic individual! Although my doggy day care was last minute, I felt reassured that Semi was in good hands. Truly someone you can trust with your pups!”


“Korie took great care of my dog Wolfie. Her response was fast to my request for daycare and Korie’s dog Ozzy played well with Wolfie. They even went on three walks too! Wolfie was a very relaxed pup when I picked him up. Thanks Korie!”


About: Happy, loving, patient and playful pupsitters who have experience working as kennel manager, dogsitter, and lifelong dog lovers. We love and care for all creatures big and small and happen to love dogs as though they were our own children (and they are.) My partner Jessie and I share all dog duties in our house. Someone is around the house every day of the week, as Jessie often works from home, and our two pups are always home. We strive to never leave our own pups alone for no more than 4 hours so there's always time and room for bathroom breaks. And if the weather is nice we leave the backyard door open for them to roam free (in a fenced area). It is the most ideal place for a dog to have room to move about, activities to entertain, and loving caretakers to help them live their best life. We have a fenced in yard and plenty of space to roam, along with healthy wildlife distractions, fun toys, plenty of snacks, and generous room inside the house for everyone to feel cozy, warm or cool, and always nurtured.

About: I have grown up with dog in my life, Walking them is my job, also my work out. 1 miles at least walk per walk. I grown up with big dogs , walking them is the best way to waste their energy. Also add some work out on my own. For visiting, I work in the 8am-4:30pm , during weekdays anytime before 8 or after 4:30 pm will work for me. On the weekend I usually I can walk them anytime. I live in an apartment I do believe that if you walk him well enough (longer distances, let them smell around) they don’t need a yard. I walk my dog at least one mile per walk. I also play with them at home to make sure they are good to go.

“My little Westie loves Suellen and her two sweet dogs. They treat her like one of their own. It's great for me to be able to drop her off for the day, knowing she'll have fun and be safe.”


“Small space, huge heart. Julie was great with our exuberant furbabies, Boss and Inja, and they clearly had a wonderful time! While there's not a huge space for them to run, they got plenty of activity and action playing with her and the other pups, and they came home exhausted even after sneaking in snuggles with Julie on the couch. Very happy with their experience and looking forward to them spending more time with Julie, Duncan, and the other visiting pack members!”


About: We have a combined 30+ years of caring for all types of animals, including cats, dogs, reptiles, & fish (and rabbits and chickens!). We’ve worked with pets of many different breeds and ages, including puppy/kitten and senior care. Medication needs or specific care requests? We're here for you! When we care for your pet, we'll work as a team to ensure your pet is comfortable, loved, and stimulated while you're away. Drop ins - Food, water, litter, walks, cuddles, medications, enrichment, or whatever your pet needs - we are happy to accommodate. Boarding - We live in the Grandview Commons neighborhood on the East side of Madison. We are WFH DINKS, single-family home with a fenced yard and are happy owners of fish, 1 dog, and 2 cats (and too many plants!). Book today for all your pet care needs! We have flexible schedules that allow us to care for pets during the week and on weekends - whether that includes boarding or drop-in visits. We will respect your pet care plan as outlined in any instruction or communication prior to our time with your pet/s. We are an easy going pair of sitters that enjoy giving your animals the attention they deserve.

“I'm thrilled I found this family to take care of my chocolate lab. Came to Madison for a wedding looking to find someone to wear out my dog. I sure did find great family. They have nice size property for her to run around, toys , and a bonus kiddie water pool. I picked her up and she fell asleep right away before we made it too the hotel. Thank you. I will use them again whenever I'm back in Madison.”


About: I grew up training and showing dogs and will always have a soft spot in my heart for them, especially seniors! I pet-sit for friends and family regularly, and recently decided to open my home to some new furry friends that will keep me company while I work from home. I work from home regularly and love to have a companion during the day, especially for lunch time walks. Overnight boarding works great too with my flexible schedule! I will do my best to follow your dog's regular schedule so that they are comfortable! I can easily let dogs out during the day. I have experience giving dogs medicine (usually a marshmallow or some cheese will do the trick!) As I'm home all day, I could accommodate a dog with separation anxiety.


“Sarah is such a welcoming, warm, easy going, and responsible dog sitter. My puppy, Tilly, and her dog, Millie, and the other dog, Sam, she was sitting were so clearly having a blast all day, each day that I left Tilly with Sarah. Tilly was even digging her heels in when it was time to leave after a few days with Sarah and Millie! Couldn't ask for a more pure and wholehearted endorsement than that! Thank you Sarah!”


“Our 3 dogs love going to Kara’s. They run in the door and barely look back at us. We know they’re having a great time by the photos Kara sends us during their stay. She takes wonderful care of them.”

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Emily K.Star Sitter

“Emily took great care of our pup, Toby! He is 10 weeks old and she was capable of managing the extra needs of a young puppy. Emily was very communicative and responsive to messages. We would send our pup to be cared for by her again!”


Cynthia H.Star Sitter

“Cynthia’s pupdates are THE BEST! I look forward to her primo photos & pupdates every time. My pup Popsicle gets so excited when she sees Cynthia. Hands-down the most thoughtful, caring pup-sitter that I have encountered. ✨”


Sarah M.Star Sitter

“Perfect set up for dog heaven. I needed a sitter for the day and I’m pretty sure my dog had the time of his life. He took a solid nap after picking him up!”


Gilian S.Star Sitter

“Gillian is great! Great with ou one year old puppy! Great communicator! Marley loves her and loves going to day care with Gillian and the other pups!”


Laura S.Star Sitter

“Truck had a blast and was very well taken care of. She sent photos and updates the entire time, and it made the entire experience really easy. Thank you!!”


Briana M.

“Briana is such a kind and empathetic individual! Although my doggy day care was last minute, I felt reassured that Semi was in good hands. Truly someone you can trust with your pups!”


Korie L.


“Korie took great care of my dog Wolfie. Her response was fast to my request for daycare and Korie’s dog Ozzy played well with Wolfie. They even went on three walks too! Wolfie was a very relaxed pup when I picked him up. Thanks Korie!”


Brian & Jessie B.
About: Happy, loving, patient and playful pupsitters who have experience working as kennel manager, dogsitter, and lifelong dog lovers. We love and care for all creatures big and small and happen to love dogs as though they were our own children (and they are.) My partner Jessie and I share all dog duties in our house. Someone is around the house every day of the week, as Jessie often works from home, and our two pups are always home. We strive to never leave our own pups alone for no more than 4 hours so there's always time and room for bathroom breaks. And if the weather is nice we leave the backyard door open for them to roam free (in a fenced area). It is the most ideal place for a dog to have room to move about, activities to entertain, and loving caretakers to help them live their best life. We have a fenced in yard and plenty of space to roam, along with healthy wildlife distractions, fun toys, plenty of snacks, and generous room inside the house for everyone to feel cozy, warm or cool, and always nurtured.


Autumn H.Star Sitter
About: I have grown up with dog in my life, Walking them is my job, also my work out. 1 miles at least walk per walk. I grown up with big dogs , walking them is the best way to waste their energy. Also add some work out on my own. For visiting, I work in the 8am-4:30pm , during weekdays anytime before 8 or after 4:30 pm will work for me. On the weekend I usually I can walk them anytime. I live in an apartment I do believe that if you walk him well enough (longer distances, let them smell around) they don’t need a yard. I walk my dog at least one mile per walk. I also play with them at home to make sure they are good to go.


Megan T.Star Sitter

“Megan was absolutely wonderful! Very friendly and I loved the updates. Lazlo was very Happy and had a Fun day 🐕🦺😃 Will Definitely be a repeat client!!”


Suellen A.Star Sitter

“My little Westie loves Suellen and her two sweet dogs. They treat her like one of their own. It's great for me to be able to drop her off for the day, knowing she'll have fun and be safe.”


Julie D.
Star Sitter


“Small space, huge heart. Julie was great with our exuberant furbabies, Boss and Inja, and they clearly had a wonderful time! While there's not a huge space for them to run, they got plenty of activity and action playing with her and the other pups, and they came home exhausted even after sneaking in snuggles with Julie on the couch. Very happy with their experience and looking forward to them spending more time with Julie, Duncan, and the other visiting pack members!”


Jessica G.

“Remy seemed to really enjoy his stays with Jessica. Easy to communicate and really helped me in a pinch!”


Meghan & Jacob D.Star Sitter
About: We have a combined 30+ years of caring for all types of animals, including cats, dogs, reptiles, & fish (and rabbits and chickens!). We’ve worked with pets of many different breeds and ages, including puppy/kitten and senior care. Medication needs or specific care requests? We're here for you! When we care for your pet, we'll work as a team to ensure your pet is comfortable, loved, and stimulated while you're away. Drop ins - Food, water, litter, walks, cuddles, medications, enrichment, or whatever your pet needs - we are happy to accommodate. Boarding - We live in the Grandview Commons neighborhood on the East side of Madison. We are WFH DINKS, single-family home with a fenced yard and are happy owners of fish, 1 dog, and 2 cats (and too many plants!). Book today for all your pet care needs! We have flexible schedules that allow us to care for pets during the week and on weekends - whether that includes boarding or drop-in visits. We will respect your pet care plan as outlined in any instruction or communication prior to our time with your pet/s. We are an easy going pair of sitters that enjoy giving your animals the attention they deserve.


Rebekah & Alex N.

“I'm thrilled I found this family to take care of my chocolate lab. Came to Madison for a wedding looking to find someone to wear out my dog. I sure did find great family. They have nice size property for her to run around, toys , and a bonus kiddie water pool. I picked her up and she fell asleep right away before we made it too the hotel. Thank you. I will use them again whenever I'm back in Madison.”


Libby M.
“We couldn’t have asked for a better sitter than Libby! She took care of our dog for 10 days while we were out of the country, and we felt totally at ease the entire time. Libby was incredibly responsive, provided regular updates, and sent plenty of photos that kept us connected and reassured. It was clear our pup was in great hands and getting lots of love and attention. We came home to a happy, well-cared-for dog, and we’re so grateful to have found someone so dependable and thoughtful. Highly recommend Libby to anyone looking for a caring and communicative sitter!”




Sarah B.


“Sarah is such a welcoming, warm, easy going, and responsible dog sitter. My puppy, Tilly, and her dog, Millie, and the other dog, Sam, she was sitting were so clearly having a blast all day, each day that I left Tilly with Sarah. Tilly was even digging her heels in when it was time to leave after a few days with Sarah and Millie! Couldn't ask for a more pure and wholehearted endorsement than that! Thank you Sarah!”


Kara S.

“Our 3 dogs love going to Kara’s. They run in the door and barely look back at us. We know they’re having a great time by the photos Kara sends us during their stay. She takes wonderful care of them.”


Tracy S.

“Tracy was so patient with our elderly dog's needs and actions. Happy definitely had a good time and was exhausted each night! Great availability.”


Tony D.

“Bogey had such a great time at Tony's. His dog, Yoshi, gets along great with Bogey. He came home very tired, but very happy! Thanks Tony. Looking forward to our next stay”
High Crossing dog parents share their Rover experiences
We are very grateful to Tracy. She took care of our adolescent dog with his first experience with daycare. We had a sudden family emergency that required someone to look after our pub. She was open and communicative which was very helpful. Would recommend to others.

Popular requests near you
Select a filter and find qualifying High Crossing sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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 dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Doggy Day Care FAQs
Frequently asked questions about Rover
Typically, sitters offering doggy day care on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in High Crossing.
High Crossing 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 High Crossing 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
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.
