Pet Sitting & Drop Ins in Glen Oak Hills, 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 Glen Oak Hills pet sitters

“Julie was great on her 1st day of drop ins with Lakyn, prompt & flexible, very communicative & even sent photos. Definitely look forward to continuing our relationship for Lakyn's needs.”


“Ann made my boyfriend and I feel at ease with being away from her. Ann sent amazing updates about our little pup with every little detail that we loved! Will definitely ask Ann to watch our little girl in the future :)”


“I'm so relieved to have Maiya. I've already rebooked her for my next trip, and I don't even have my tickets for the trip bought yet. Jackson cat is a typical cat, but his stamp of approval is on this review too. As indicated by photo evidence of him coming out from under his bed for a snack on DAY 2! Snag her if you're lucky enough to have the chance.”


“The pets are always excited to have Kim come over and we feel confident they are in good hands. She always goes above and beyond and is willing to work with us for last minute requests:)”


“Lydia did a great job looking after my cat while I was out of town for a few days. She provided daily updates and I returned home to a happy kitty. Im a repeat customer. Next time I plan on leaving town Lydia will be the first person I call :)”


“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!”



“My dogs really like Allegra and she seems to be great with them too. She was great during our meet and greet and spent time to get to know the pups. Will hire again for sure!”


“Went with Sabrina again! She does such a great job with my picky, old toy poodle lol. Chewy takes a while to warm up to people so I'm glad he is in good hands with Sabrina. Was a no-brainer going with her and I recommend her!”


“Annie was great with Maggie! She was very responsive and gave updates on Maggie whenever I asked. I am really appreciative of her care of Maggie.”



“Karly was wonderful. It was our first time away from our kitties and such a relief to know that they were in attentive and caring hands. Karly was super reliable and helpful, and kept us updated. Would definitely recommend her as a sitter.”



“Thank you for taking such good care of our fur baby! This was our first time using Rover and traveling away from our pup after recently moving. Jennifer was an excellent sitter with great communication and great patience with our sensitive pup. Highly recommend!”


About: I am a dog mom of two very anxious and reactive rescue pups (both under two year olds). I have experience administering oral medication and handling severe dog anxiety. I am patient and cautious, and overall want your pet to have the best experience. I am a real estate agent, so my schedule is extremely flexible and I happy to spend 15-30 mins checking in and walking your furry friend during the day or evenings. I just ask for a 48 hour heads up so that I can coordinate my schedule. If you live nearby, and would like your pet to have some off-leash enrichment time, I have a fenced in yard with plenty of sniff spots!

About: I have experience with all types of pets, from high-energy companions to more laid-back, relaxed ones. Growing up with dogs, working as a social worker at a veterinary clinic, and being a pet owner myself, I understand how important it is to provide your pet with the love and care they deserve. Every pet has its own unique personality, and I’m here to cater to their individual needs—whether your dog requires an extra-long walk or your cat needs brushing and nail trimming. I’ve got you covered! I work from 8:00-4:30 most days of the week. I’m available for walks and drop in visits at any point on the weekends. I can also make walks and drop in visits work anytime before and after my workday during the week. For all services, whether it's walking your dog or housesitting, I like to gather all the details. I understand that you’re trusting me to take care of your pet, and I want to make sure I meet your expectations. To do this, I'll learn about your pet’s routine, how they behave during walks, their personality, and any special care instructions that will help make the experience better for everyone involved.

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

About: I have had dogs my entire life. They ranged from puppies all the way to them becoming senior dogs, and they all came from very different backgrounds. I am especially good with senior dogs. My childhood dog eventually had severe arthritis and needed medication and some extra help. I would do anything for her that helped her feel more comfortable! I also puppysit for some family members so I am also used to the craziness a puppy can bring! I am currently available most days at any time until August 11. My cat does need medication at 8pm, but any other time of the day works for me! I can care for your pets however you need in your home! Whether it's going on a walk, playing outside, or staying inside, whatever is best for them is doable!


“Sarah is the best! Thorough and kind, she always makes sure your pet(s) get their basic needs met, and even some pets and loving along the way. We've booked with her multiple times and has our trust :)”


“Katia was very communicative and prompt. I haven't been on a vacation in years, and even though it was only for a night, she put my mind at ease by dropping in on my cats and tortoise!”

Loving pet sitters in your neighborhood
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Julie A.Star Sitter

“Julie was great on her 1st day of drop ins with Lakyn, prompt & flexible, very communicative & even sent photos. Definitely look forward to continuing our relationship for Lakyn's needs.”


Ann V.Star Sitter

“Ann made my boyfriend and I feel at ease with being away from her. Ann sent amazing updates about our little pup with every little detail that we loved! Will definitely ask Ann to watch our little girl in the future :)”


Maiya W.Star Sitter

“I'm so relieved to have Maiya. I've already rebooked her for my next trip, and I don't even have my tickets for the trip bought yet. Jackson cat is a typical cat, but his stamp of approval is on this review too. As indicated by photo evidence of him coming out from under his bed for a snack on DAY 2! Snag her if you're lucky enough to have the chance.”


Kim M.

“The pets are always excited to have Kim come over and we feel confident they are in good hands. She always goes above and beyond and is willing to work with us for last minute requests:)”


Lydia S.

“Lydia did a great job looking after my cat while I was out of town for a few days. She provided daily updates and I returned home to a happy kitty. Im a repeat customer. Next time I plan on leaving town Lydia will be the first person I call :)”


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!”


Anna O.Star Sitter

“Anna did a great job with our girls! We received photos and a quick update on how they were doing during her check in. Couldn't have asked for a better experience.”




Allegra R.
Star Sitter


“My dogs really like Allegra and she seems to be great with them too. She was great during our meet and greet and spent time to get to know the pups. Will hire again for sure!”


Sabrina S.

“Went with Sabrina again! She does such a great job with my picky, old toy poodle lol. Chewy takes a while to warm up to people so I'm glad he is in good hands with Sabrina. Was a no-brainer going with her and I recommend her!”


Annie J.
Star Sitter


“Annie was great with Maggie! She was very responsive and gave updates on Maggie whenever I asked. I am really appreciative of her care of Maggie.”


Cleda W.
Star Sitter


“Cleda took good care of Bailey while we were gone. I could tell from the pictures she sent that Bailey loved having her visit. I would definitely book again.”




Karly M.
Star Sitter


“Karly was wonderful. It was our first time away from our kitties and such a relief to know that they were in attentive and caring hands. Karly was super reliable and helpful, and kept us updated. Would definitely recommend her as a sitter.”




Jennifer L.
Star Sitter


“Thank you for taking such good care of our fur baby! This was our first time using Rover and traveling away from our pup after recently moving. Jennifer was an excellent sitter with great communication and great patience with our sensitive pup. Highly recommend!”


Corinne B.

“Corinne is quick to respond to messages and very personable. She did a great job with our almost 12 yo rescue dog!”


Amaya B.
“Amaya is extremely caring and kind towards everyone, pets and humans all around. She is always eager to support your pets the best she can, through walking, enrichment, playing, or whatever else may be needed. I always appreciate her transparency and reliability, always using such clear communication. I’ve had the pleasure of seeing Amaya not only with her own cats and dogs, but with my deaf dog and other animals as well. She is a wonderful person and a great companion to help out when needed.”


Aubrey T.
“Aubrey is great with animals! She even deals with them on the daily as her profession. She’s had dogs since she was 3 and is great with my dog. He loves when she takes him on walks and gives him treats!”


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!”


Ella O.
“Ella has lived with pets her entire life. She has actively assisted in the care of her families 3 dogs and 2 cats. Whether it was feeding, playing, walking, or simply cuddling with them, she did it all! Ella loves all animals, is trustworthy and dependable. Ella has a soft spot for senior pets, and she even adopted a senior cat from a shelter. You can trust that your pet will get all the love and attention with Ella as their caretaker!”




Sarah S.Star Sitter

“Sarah is the best! Thorough and kind, she always makes sure your pet(s) get their basic needs met, and even some pets and loving along the way. We've booked with her multiple times and has our trust :)”


Katia W.

“Katia was very communicative and prompt. I haven't been on a vacation in years, and even though it was only for a night, she put my mind at ease by dropping in on my cats and tortoise!”
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 Glen Oak Hills.
Rover makes it easy to find Glen Oak Hills 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.
