Pet Sitting & Drop Ins in Cherokee Garden, Madison, WI
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Cherokee Garden pet sitters

“Jen was very attentive with Iroh and made sure that he was well cared for in our absence. I would happily book her again and recommend her to any pet parent!”


“Jolie has been super helpful. She loves animals and cares about them. She also respects and meets pet owners' needs. I couldn’t be happier with booking her. She is taking care of my babies, and I will definitely work with her again in the future.”


“Maggie went above and beyond - including braving a winter snowstorm - to make sure our cat was well cared for while we were out of town. Couldn’t recommend more highly!”


“Laura is great! She arrives on time and my dog seems to love going with her. She is very helpful and knowledgeable about dogs. I couldn't recommend her more!”


“It was wonderful to entrust Grace with our full house of animals! She went above and beyond in both prep for the visit and during - we are greatly appreciative and will book with her again! Thank you!”


“Communication with Annmarie was easy and clear and her updates were very appreciated. My cat and dog clearly had a nice time with her. Would definitely book with her again.”



“Megan was wonderful with our senior cat and dog while we were away for several days! She was always on time for her scheduled visits, gave lots of detailed updates, and made us feel like our pets were truly taken care of. We would love to rebook with her in the future!”


“Anne did a fabulous job!! Her sweet, calm energy put my anxious cats at ease. She did wonderful with my finicky instructions, sent helpful updates with pictures, and took great care with my girls. I was able to relax and enjoy my vacation knowing they were in good hands.”


About: I have experience taking care of a high medical needs cat. I also have experience with deaf and blind cats. I understand each pet is an individual and will adjust my care as I get to know them. Some pets love human interaction and others need their space. I’m absolutely ready to kiss and hug them or give them the distance they need to feel safe. Nothing like the smell of fresh litter in the morning! I am a cat mom to 2 playful, cuddly adopted babies. I recently became a volunteer at a cat shelter, which gives me so much purpose. I have a full time job Monday-Friday. I am looking to occasionally pet sit on weekends and early mornings on weekdays. Home is a sacred place. I will treat your pets and your space respectfully. I can send you all the photos you need to feel comfortable, or video call you. I am comfortable cleaning up after your pet, and giving them all the cuddles and words of affirmation they need while you are away.

“Jennifer was great with both of my dogs. One is a bit fearful but she was able to win him over easily. They were so nice and relaxed when I got home, it was so nice to know they were so well cared for”


“I could not recommend Megan more! She is lovely, sends great updates, wonderfully silly and also genuinely great pictures, and, best of all, my cat warmed up to her in a way that she has not warmed up to anyone else! Overall, I have absolutely nothing negative to say and I am so grateful that Megan was so great with my cat!”


“Samantha was great with both of my dogs. She was reliable, communicative, and followed their routines exactly. I felt completely comfortable having her check-in on our pups. She sends me lots of pics.”


“Salem is an excellent sitter and responded to our last minute request for an extra care of cat sitting. Highly recommend, very reliable and communicative sitter. Thanks again, Salem!”


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.

“Sarah took such great care of Pita! We appreciated the cute photos and pet POV updates that let us know how much Pita was loving Sarah’s visits. I would 100% recommend Sarah for any pet care needs!”


About: My wife and I have extensive experience with animals, having run dog boarding services and worked at dog daycares. I grew up with various animals, including six dogs, and have always cared for them with love and respect. We’re confident in handling any situation that may arise while caring for pets and treat them like family. Our multi-level home near Dane County Airport offers plenty of space for pets to play and relax, including a large backyard with a 6-foot privacy fence. My wife and I both have flexible work schedules, so someone is almost always home with our pups! We will try our best to accommodate any special needs for scheduling. We have a fenced in large yard and two friendly dogs to play with yours! We also have secure gates to section off our home if needed and multiple sizes of dog beds for relaxing and crates if your pup is crate trained and/or sleeps in a crate.
Loving pet sitters in your neighborhood
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Jen D.Star Sitter

“Jen was very attentive with Iroh and made sure that he was well cared for in our absence. I would happily book her again and recommend her to any pet parent!”


Jolie ZevallosStar Sitter

“Jolie has been super helpful. She loves animals and cares about them. She also respects and meets pet owners' needs. I couldn’t be happier with booking her. She is taking care of my babies, and I will definitely work with her again in the future.”


Maggie P.Star Sitter

“Maggie went above and beyond - including braving a winter snowstorm - to make sure our cat was well cared for while we were out of town. Couldn’t recommend more highly!”


Steve J.Star Sitter

“Bro is efficient. Treats his clients like family bringing in mails and I really appreciate it. 4th week watching my meowies and I couldnt be anymore but greatful.”


Laura S.Star Sitter

“Laura is great! She arrives on time and my dog seems to love going with her. She is very helpful and knowledgeable about dogs. I couldn't recommend her more!”


TAYLOR P.

“Taylor did a great job checking in on my kitty while we were away. She did exactly what I asked of her and felt my cat and home were in good hands.”


Grace N.Star Sitter

“It was wonderful to entrust Grace with our full house of animals! She went above and beyond in both prep for the visit and during - we are greatly appreciative and will book with her again! Thank you!”


Zachary N.

“Consistently great! Another few days of visits with Zachary in which I had 100% worries for my senior dog while I was out of town!”


Annmarie S.Star Sitter

“Communication with Annmarie was easy and clear and her updates were very appreciated. My cat and dog clearly had a nice time with her. Would definitely book with her again.”




Megan B.Star Sitter

“Megan was wonderful with our senior cat and dog while we were away for several days! She was always on time for her scheduled visits, gave lots of detailed updates, and made us feel like our pets were truly taken care of. We would love to rebook with her in the future!”


Anne S.Star Sitter

“Anne did a fabulous job!! Her sweet, calm energy put my anxious cats at ease. She did wonderful with my finicky instructions, sent helpful updates with pictures, and took great care with my girls. I was able to relax and enjoy my vacation knowing they were in good hands.”


Vanessa U.
“Vanessa is such a kind and empathetic soul! My two dogs adore her with all their beings and always want to go home with her haha. She's very detail-oriented and incredibly trustworthy. She has the sweetest touch with cats, and you can't help but feel the warmth and kindness radiating from her when in a room with your babies. As a fellow Rover sitter, I trust her wholeheartedly with my pets and know anyone would be lucky to have her as your sitter.”


Jennifer J.

“Jennifer was great with both of my dogs. One is a bit fearful but she was able to win him over easily. They were so nice and relaxed when I got home, it was so nice to know they were so well cared for”


Megan T.Star Sitter

“I could not recommend Megan more! She is lovely, sends great updates, wonderfully silly and also genuinely great pictures, and, best of all, my cat warmed up to her in a way that she has not warmed up to anyone else! Overall, I have absolutely nothing negative to say and I am so grateful that Megan was so great with my cat!”


Samantha S.

“Samantha was great with both of my dogs. She was reliable, communicative, and followed their routines exactly. I felt completely comfortable having her check-in on our pups. She sends me lots of pics.”


Salem E.

“Salem is an excellent sitter and responded to our last minute request for an extra care of cat sitting. Highly recommend, very reliable and communicative sitter. Thanks again, Salem!”


Anna N.

“I have booked Anna three times and she has been wonderful every time. She sends me the cutest picture updates. I defiantly recommend her, we will be using her in the future again.”


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.


Sarah W.Star Sitter

“Sarah took such great care of Pita! We appreciated the cute photos and pet POV updates that let us know how much Pita was loving Sarah’s visits. I would 100% recommend Sarah for any pet care needs!”


Nick K.

“Nick has a special connection with animals! All of my cats and dogs love him!! He has the energy and consistent positive control to run with my 115 lb GSD and the playful, sit on the floor , unintimidating, gentle handling of my 5 little dogs, 3 to 15 lbs. He has been an excellent, responsible, caring petsitter and dog walker. I highly recommend him for ANY pet!”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets 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 pet 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.
Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Cherokee Garden.
Rover makes it easy to find Cherokee Garden pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
