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

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Wyndemere pet sitters

“Ann was incredible! She was so sweet and kind our cats Petri and Krobus as well as to us humans. Ann also took phenomenal photos of our cats (I am in awe!!) and left detailed notes with each visit. I'm so grateful she was able to watch our cats -- they were in excellent hands. Ann made the whole experience easy and gave us so much peace of mind!”


“Maiya is amazing and sent us pictures everyday to check in. Our cat loved her (and our cat does not like strangers). Super accommodating and professional. We highly recommend her!”


“Laura was great with our new puppy! She was easy to get in touch with on the app and was such a joy to work with. We definitely hope to use her services again in the future!”


“Krista did a great job taking care of our kitty, Claude! Claude doesn’t let just anyone pet him and play with him right away but apparently he thinks Krista is his new bestie because he walked right up to the door to greet her and demand pets every night! Our cat was very well cared for while we were away. 😊”


“Ivy and especially Bernard enjoyed having Lydia drop in on them while we were out of town for the holidays. Lydia gave them lots of care and affection. She even started teaching Bernard a new trick! We appreciate that she gave us updates with photos and brought in our mail for us. We would happily have Lydia sit for us again.”



“Allegra has been great with Ozzie and very supportive of our schedule with helping out with his potty breaks, dinners and play times. Ozzie loves to see her every time she visits! Thank you again Allegra for looking after Ozzie 😁🙏🏼”


“Highly recommend Sabrina! She adapted to Chewbacca's needs and even introduced ways to get him to eat that I didn't even think about. Chewy's a stubborn, grumpy old poodle and he opened up to her!! Sabrina was easy to communicate with and sent plenty of updates to keep me in the loop. She went above and beyond with everything and treated Chewy like her own. I'll definitely choose her next time Chewy needs a sitter!”


“I chose Kim for my first Rover experience to take care of my cat while I was away for a week. She showed genuine care and interest in my cat , provided daily pictures and updates while I was away , and was always quick to respond if and when needed. She is very trustworthy and she’ll be an obvious choice for the next time I need someone to watch my cat ! I have no hesitation and give my full enthusiasm to recommend her to anybody looking for the right caretaker for your pet.”

“She did such a good job with my cats. I had one who recently had teeth pulled, so both of my cats were getting fed largely different diets. She was able to manage them both. Also my very shy cat was even comfortable coming out to see her every day. Highly recommend”


About: Hi, I’m Kaitlyn and I’ve lived with dogs for almost 20 years! I’ve helped family, neighbors and friends with pets of all ages, sizes and personalities. My experience has provided insight into how to comfortably care for most pets! I’m currently working at a dental clinic in the Madison area from Monday - Thursday. While work days can be busy, I can be readily available for drop-ins and walks over the lunch hour if needed. There is a large open field behind my apartment that is used by many dog owners to let their fur babies have some freedom throughout the day

“Evee took excellent care of our kitties (and fish)! She sent daily communication and texted if she had any questions. We will definitely be asking her to pet sit for us again!”


“I strongly recommend Annie! She is super easy to work with. Although we had a last minute appointment, Annie was very responsive and quickly arrange a meet and greet. She followed our instructions meticulously, provided super detailed descriptions of her activities with our cat, and sent a lot of lovely pictures, which was very assuring and substantially eased our anxiety away from our cat. Thank you, Annie!!”



“I messaged Whitney at the absolute last minute because I realized I forgot to get someone to check in on my kitty while we were out of town for Thanksgiving. Whitney replied quickly and said she’d be happy to help while we were away— what a relief! She was great and my skittish cat was happy to come out and get some pets from her. Will definitely book Whitney again!”


“Very thorough and follows direction and house rules. Great communication and does really well with AdaRae. She seems to be very fond of her new friend! Will definitely be rebooking with Chenghao.”



“Hannah was awesome with our 11 yo rescue dog, very caring and spent quality time with her. Hannah is very responsible, showed up promptly, and Luna was very happy with her visit (we were too)!”



“Jennifer did an excellent job with our cat Lunar while we were on vacation for a week. Hour long visits every day with picture updates. Would recommend to any cat owner.”


“Courtney went above and beyond for my beloved dog. She gave me updates and connected well with us. I will definitely use her again. I'm so glad we've been able to establish this relationship!”


“Would absolutely recommend Alisyn!! She has been wonderful with our older dog, Indy, over the last year. When we added a second dog (a young rescue with heartworm disease), I knew I could trust Alisyn to take great care of Eeva and keep her safe during treatment, too. We are so grateful to have such a dependable, experienced, and compassionate person watching and walking our pups!”

Loving pet sitters in your neighborhood
Search Results


Julie A.Star Sitter

“Julie is awesome. She is kind and patient with senior dogs. She’s reliable and jumps in to assist in even if n situations where there is a short notice. Thank you Julie”


Ann V.Star Sitter

“Ann was incredible! She was so sweet and kind our cats Petri and Krobus as well as to us humans. Ann also took phenomenal photos of our cats (I am in awe!!) and left detailed notes with each visit. I'm so grateful she was able to watch our cats -- they were in excellent hands. Ann made the whole experience easy and gave us so much peace of mind!”


Maiya W.Star Sitter

“Maiya is amazing and sent us pictures everyday to check in. Our cat loved her (and our cat does not like strangers). Super accommodating and professional. We highly recommend her!”


Laura D.Star Sitter

“Laura was great with our new puppy! She was easy to get in touch with on the app and was such a joy to work with. We definitely hope to use her services again in the future!”


Krista C.Star Sitter

“Krista did a great job taking care of our kitty, Claude! Claude doesn’t let just anyone pet him and play with him right away but apparently he thinks Krista is his new bestie because he walked right up to the door to greet her and demand pets every night! Our cat was very well cared for while we were away. 😊”


Lydia S.

“Ivy and especially Bernard enjoyed having Lydia drop in on them while we were out of town for the holidays. Lydia gave them lots of care and affection. She even started teaching Bernard a new trick! We appreciate that she gave us updates with photos and brought in our mail for us. We would happily have Lydia sit for us again.”




Allegra R.
Star Sitter


“Allegra has been great with Ozzie and very supportive of our schedule with helping out with his potty breaks, dinners and play times. Ozzie loves to see her every time she visits! Thank you again Allegra for looking after Ozzie 😁🙏🏼”


Sabrina S.

“Highly recommend Sabrina! She adapted to Chewbacca's needs and even introduced ways to get him to eat that I didn't even think about. Chewy's a stubborn, grumpy old poodle and he opened up to her!! Sabrina was easy to communicate with and sent plenty of updates to keep me in the loop. She went above and beyond with everything and treated Chewy like her own. I'll definitely choose her next time Chewy needs a sitter!”


Kim M.
“I chose Kim for my first Rover experience to take care of my cat while I was away for a week. She showed genuine care and interest in my cat , provided daily pictures and updates while I was away , and was always quick to respond if and when needed. She is very trustworthy and she’ll be an obvious choice for the next time I need someone to watch my cat ! I have no hesitation and give my full enthusiasm to recommend her to anybody looking for the right caretaker for your pet.”


Cleda W.
Star Sitter


“She did such a good job with my cats. I had one who recently had teeth pulled, so both of my cats were getting fed largely different diets. She was able to manage them both. Also my very shy cat was even comfortable coming out to see her every day. Highly recommend”


Kaitlyn B.Star Sitter
“Kaitlyn is very responsible and always takes great care of my two cattle dog mixes! They’re very high energy, but Kaitlyn always does a great job keeping up with them. Each time they stay with her, regardless of the amount of time, I get great pictures and updates, keeping me up to date on what they are up to!”


Yvonne L.Star Sitter

“Evee took excellent care of our kitties (and fish)! She sent daily communication and texted if she had any questions. We will definitely be asking her to pet sit for us again!”


Annie J.
Star Sitter


“I strongly recommend Annie! She is super easy to work with. Although we had a last minute appointment, Annie was very responsive and quickly arrange a meet and greet. She followed our instructions meticulously, provided super detailed descriptions of her activities with our cat, and sent a lot of lovely pictures, which was very assuring and substantially eased our anxiety away from our cat. Thank you, Annie!!”




Whitney H.


“I messaged Whitney at the absolute last minute because I realized I forgot to get someone to check in on my kitty while we were out of town for Thanksgiving. Whitney replied quickly and said she’d be happy to help while we were away— what a relief! She was great and my skittish cat was happy to come out and get some pets from her. Will definitely book Whitney again!”


Chenghao X.

“Very thorough and follows direction and house rules. Great communication and does really well with AdaRae. She seems to be very fond of her new friend! Will definitely be rebooking with Chenghao.”


Anna H.

“Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!”




Hannah I.


“Hannah was awesome with our 11 yo rescue dog, very caring and spent quality time with her. Hannah is very responsible, showed up promptly, and Luna was very happy with her visit (we were too)!”




Jennifer L.
Star Sitter


“Jennifer did an excellent job with our cat Lunar while we were on vacation for a week. Hour long visits every day with picture updates. Would recommend to any cat owner.”


Courtney E.Star Sitter

“Courtney went above and beyond for my beloved dog. She gave me updates and connected well with us. I will definitely use her again. I'm so glad we've been able to establish this relationship!”


Alisyn L.

“Would absolutely recommend Alisyn!! She has been wonderful with our older dog, Indy, over the last year. When we added a second dog (a young rescue with heartworm disease), I knew I could trust Alisyn to take great care of Eeva and keep her safe during treatment, too. We are so grateful to have such a dependable, experienced, and compassionate person watching and walking our pups!”
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 Wyndemere.
Rover makes it easy to find Wyndemere 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.
