Pet Sitting & Drop Ins in Westchester Gardens, Madison, WI
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
More resources
A focus on safety
Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check. Learn more about RoverProtect
Top rated Westchester Gardens pet sitters
“Another great visit from Jen. Love having her come over and take care of my dogs because I know they’re gonna be well careful while I’m gone.”
“Amanda is great with checking in on our cat while we're away! She goes above and beyond, and is someone I'd absolutely not hesitate to use in the future.”
“Great communication!”
“Easy last minute booking, I literally had to worry about nothing. Many thanks!!”
“Joan was a wonderful sitter for our two cats! She was super communicative, sent us lots of pictures, and was always timely. Would highly recommend!!”
“Kathryn is amazing. Extremely attentive to my baby’s needs and super flexible with our schedule. Her communication goes beyond expectation and has made our experience of rover great!”
About: I am a lifelong animal lover & care taker. I also own a small business making healthy pet treats, so your special fur face will be spoiled! I have experience with reactive dogs, behavioral problems, senior animals, medical issues, & a wide variety of species. I base my care around the animals needs, not my schedule. I am patient, steady, & calm. I have loads of engagement toys, puzzles & activities to keep your pet happy & stimulated. I have a very flexible schedule & work from home, so I can adjust around you & your pets' needs whether it's early morning, last minute, or before bed. I do not have a fenced yard, so I do not leave dogs outside at my home. I walk & take park trips multiple times a day. I have 3 dogs & a cat who are used to new friends visiting. I do not crate my dogs in my home, but am happy to in your home.
“Maggie was fantastic! We loved the daily picture updates. She made it so easy and stress free to leave our 3 cats while we were away. Will definitely rebook when we have future needs”
“Megan dropped in twice to check on George while we were away. She provided thorough updates and we knew he was in good hands. We will definitely book Megan again!”
“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.”
“Mark has come to let out dog out twice and has been great both times!! He communicates, sent photos and our doodle always have a great time with him!”
“Darby was so great! She let our three dogs out for a potty break after my dog just had surgery and took great care of him. She did a lot for my dog with him needing help using the bathroom and wearing post surgery clothes/cone. She was super loving and friendly with the dogs. Highly recommend!”
“Jilly is the best! She took care of our dogs while we were out of town for a long weekend. She came over to meet the dogs before the weekend and took notes on their routine and preferences. Throughout the weekend she provided updates and sent pictures. She loved our pups as if they were her own! Our younger dog loved that Jilly played ball with her out in the yard and played inside too. Our senior dog enjoyed the snuggling. Today Jilly came over to return our house key. The dogs were really excited to see her. Jilly took our pup outside and played ball with her for a bit. I will definitely hire Jilly again!”
“Stacy was so helpful and responded quickly with our last minute request. She did a fantastic job taking care of our flock of backyard chickens and our blind cat, catering to special instructions and sending the best photos. We really appreciate her help!”
“I’m really happy I picked Anna to look after my cats! She gave me peace of mind about leaving them while I was on vacation, knowing they’d be well cared for. I’d definitely ask her to watch them again in the future!”
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.
“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.”
About: I have been helping care for dogs both personally and as a friend since middle school. I began walking my own dog for an allowance in elementary school and loved it so I began to walk dogs for neighbors and family friends in middle school. Since then I have continued to work with dogs helping friends and family complete basic training (Sit, Stay, Lay, Leave it) and continued to learn more about dog behavior, activity needs by breed and body language. When walking your dog you can expect a minimum of a 1 mile walk/at least 20 minutes of actual walking time (or less if requested due to animal's health and abilities). I will ensure your dog is able to take in the sights and smells along the way and is engaged mentally to get some energy out. I work from home and am pretty flexible around my workday meetings. I have regularly scheduled reoccurring meetings from 9-930 on Mondays and Wednesdays but am flexible otherwise. When caring for your pet in your home you are the boss. I will follow any rules, routines or boundaries expressed by you and agreed to by me. Additionally, I will be respectful of your pet and your space. This means monitoring and respecting their behaviors and body language, keeping a clean space in your home, cleaning any mess made by feeding your animal, and cleaning accidents they may have had if provided the needed tools and supplies. When walking your dog you can expect a minimum of a 1 mile walk/at least 20 minutes of actual walking time (or less if requested due to animal's health and abilities). I will ensure your dog is able to take in the sights and smells along the way and is engaged mentally to get some energy out.
“Stephanie checked on our dogs while we were away for a long day. She left a great recap of their time together and shared a few pics. Communicative and exactly what we needed when we were away the whole day!”
“Megan is awesome!! Megan was able to help us with feeding and checking in on our cats. Our cats have different foods/needs and Megan handled it all well! Definitely will use for pet sitting again!!”
Loving pet sitters in your neighborhood
Search Results
Jen D.Star Sitter
“Another great visit from Jen. Love having her come over and take care of my dogs because I know they’re gonna be well careful while I’m gone.”
Amanda K.Star Sitter
“Amanda is great with checking in on our cat while we're away! She goes above and beyond, and is someone I'd absolutely not hesitate to use in the future.”
Autumn H.
“Great communication!”
Zachary N.
“Easy last minute booking, I literally had to worry about nothing. Many thanks!!”
Joan F.Star Sitter
“Joan was a wonderful sitter for our two cats! She was super communicative, sent us lots of pictures, and was always timely. Would highly recommend!!”
Kathryn N.Star Sitter
“Kathryn is amazing. Extremely attentive to my baby’s needs and super flexible with our schedule. Her communication goes beyond expectation and has made our experience of rover great!”
Laura S.Star Sitter
“Laura truly cared for my two dogs like they were her own. She was very attentive to their individual needs and quirks and went out of her way to make them feel comfortable with her. My one dog, Freddie, is fearful of new people and was initially skeptical of Laura. By the end of the week, she was easily his favorite human! It is a huge relief knowing your critters are well taken care of and well loved when you're away. She sent us regular photos and updates and was wonderful all around. Highly recommend!”
Maggie P.Star Sitter
“Maggie was fantastic! We loved the daily picture updates. She made it so easy and stress free to leave our 3 cats while we were away. Will definitely rebook when we have future needs”
Megan B.Star Sitter
“Megan dropped in twice to check on George while we were away. She provided thorough updates and we knew he was in good hands. We will definitely book Megan again!”
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.”
Mark L.Star Sitter
“Mark has come to let out dog out twice and has been great both times!! He communicates, sent photos and our doodle always have a great time with him!”
Darby P.
“Darby was so great! She let our three dogs out for a potty break after my dog just had surgery and took great care of him. She did a lot for my dog with him needing help using the bathroom and wearing post surgery clothes/cone. She was super loving and friendly with the dogs. Highly recommend!”
Jilly D.
“Jilly is the best! She took care of our dogs while we were out of town for a long weekend. She came over to meet the dogs before the weekend and took notes on their routine and preferences. Throughout the weekend she provided updates and sent pictures. She loved our pups as if they were her own! Our younger dog loved that Jilly played ball with her out in the yard and played inside too. Our senior dog enjoyed the snuggling. Today Jilly came over to return our house key. The dogs were really excited to see her. Jilly took our pup outside and played ball with her for a bit. I will definitely hire Jilly again!”
Stacy S.
“Stacy was so helpful and responded quickly with our last minute request. She did a fantastic job taking care of our flock of backyard chickens and our blind cat, catering to special instructions and sending the best photos. We really appreciate her help!”
Anna S.
“I’m really happy I picked Anna to look after my cats! She gave me peace of mind about leaving them while I was on vacation, knowing they’d be well cared for. I’d definitely ask her to watch them again in the future!”
Vanessa U.
“Vanessa is great with pets! She's a cat mom, with a dog mom heart. Our dogs, Pinky and Livi, can be shy around other humans, but Vanessa's warm and kind demeanor quickly melted that away. Now they run in excitement when they see her. She also help take care of our cat Cleo when we were away on a trip. Cleo is blind and elderly, so the extra effort and TLC Vanessa gave her was very appreciated!”
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.”
TAYLOR P.
“I HIGHLY recommend Taylor as a dog walker!! She's consistently reliable, responsible and the most loving dog caregiver! I feel confident that my fur baby is always in good hands with Taylor:)”
Stephanie H.Star Sitter
“Stephanie checked on our dogs while we were away for a long day. She left a great recap of their time together and shared a few pics. Communicative and exactly what we needed when we were away the whole day!”
Megan T.Star Sitter
“Megan is awesome!! Megan was able to help us with feeding and checking in on our cats. Our cats have different foods/needs and Megan handled it all well! Definitely will use for pet sitting again!!”
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 pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
3. 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 Westchester Gardens.
Rover makes it easy to find Westchester Gardens 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.
Connect anywhere with the Rover app
