Pet Sitting & Drop Ins In Wooster Square
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 Wooster Square pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Joseph is great! This was our first time using Rover. Our cat Walter loved him! Joseph was always on time and sent us photos and updates promptly! Highly recommend”

“Nicole is the best! She is wonderful with my cat and is absolutely top: responsible, caring, proactive, and communicative. I am so grateful to have found her as a sitter!”

“Yunwen was extremely responsive while setting up our drop-in visit! She also confirmed every part of our instructions while she was there, which gave us a lot of peace of mind.”

“I couldn’t have been more thankful for the service Bailee provided. She is a very caring individual and you can tell she has a love for animals. I felt relaxed and comfortable while being away from my fur baby. As this was the first trip I have been able to take I will be definitely rebooking with Bailee in the future! She was an amazing provider and very informative! Followed all directions perfectly!”

“Kelli was a great cat-sitter for our three cats. She was dedicated and made sure to spend time with all of them. One of our cats needs medication twice a day and she was able to administer it to her easily. She also played with our two younger cats, who love attention. When we came home, they appeared well taken care of. Would definitely book her again!”

“So appreciative of Grace and her care for my furbabies while I was away. I loved her check-ins and sweet photos she took of them and knew they were in great hands!!! Highly recommend!!”

“Kelsey is great! She takes my black lab out weekly, and Kay is always so happy to see her. She makes sure she goes to the bathroom and gets a good walk in - highly recommend!”

“Katelyn took great care of my cat and bunny while we were away. They are both quite needy with attention and I could tell they were both very happy for her visits. Definitely recommend!”

“Carole was absolutely amazing with our cat. She was extremely thorough, took notes on all of our preferences, and went out of her way to make the most out of the time she spent with our cat during her drop in visits (petting, brushing, playing, etc). Her great photos were also a huge bonus! My cat was much more calm and at ease when we returned from our long trip than she usually is, and I give all the credit to Carole for that!”

About: Animals have always been a big part of my life, especially cats. Over the years, I have become the go-to pet sitter within my friend group and regularly care for my friends’ cats while they are away on vacation. I also grew up informally pet sitting for neighbors and friends, giving me experience caring for pets in a variety of home environments and routines. I currently care for my own cat, Reami, a 3-year-old Ragamuffin whom I have raised since he was a kitten. Reami has anxiety-related health issues that can contribute to urinary tract problems, so I am very familiar with providing attentive, patient, and consistent care for sensitive pets. Because of his needs, I understand the importance of maintaining a calm environment, monitoring behavior closely, sticking to routines, encouraging play and enrichment, and making sure pets feel safe and comfortable while their owners are away. In addition to caring for Reami, I have also helped care for my roommates’ cats in the past, including feeding, playtime, litter box maintenance, and general companionship. Through these experiences, I have become comfortable caring for cats with different personalities, energy levels, and temperaments — from shy and anxious cats to highly social and playful ones. While I mainly prefer cat sitting, I also have some experience with dogs, including walking friends’ dogs and taking them on hikes and outdoor outings. I am happy to provide patient, attentive care tailored to each pet’s personality and comfort level. As a sitter, I prioritize communication, reliability, cleanliness, and making sure pets receive plenty of attention, affection, and enrichment while their owners are away. I am a graduate student whose lab is only a 15 minute walk away from home. My schedule is extremely flexible and except for few meetings throughout the week, my schedule is fully up to me. I am also able to leave at any point for short breaks to take pets out for walks/ check up on them. I prioritize creating a calm, safe, and comfortable environment for every pet I care for. I understand that pets — especially cats — can be sensitive to changes in routine, so I do my best to keep their schedule and environment consistent while their owners are away. When caring for pets in a client’s home, I carefully follow all instructions regarding feeding, medications, litter box cleaning, playtime, exercise, and any specific routines or preferences. I also provide regular updates and photos so owners can feel reassured that their pets are happy and well cared for. As the owner of an anxious cat with special care needs, I am very attentive to pets’ behavior, comfort, and stress levels. I value patience, cleanliness, reliability, and making sure every pet feels safe, relaxed, and loved.
“Emily dropped in once a day to check on our two cats for several days while we were away. She is EXCELLENT with communication. We never had a doubt that our cats werent getting enough love with Emily. 10/10 would ask Emily to cat-sit again! Thanks Emily!”


About: Life time owner of cats and dogs throughout his life. Has been watching friend and family pets for several years. Experienced with cats and small to medium sized dogs. I currently work full-time in office Mon-Fri, but am available weekends and weeknights (including overnight). I can be flexible to accommodate your needs. I will meet with potential clients face to face prior to accepting any request. Firstly, to go over any specific needs or questions of your pet and second, to get to know you as an owner.
“Sarah is the most loving and attentive caretaker for your fur babies. She meticulously monitored how our 19 year old Jiggs was eating and drinking while making sure our three year old Rosie was given what he also needed. Her daughter is the sweetest assistant, doling out treats and pets. You will rest easy when Sarah looks after your precious ones!”

“Chris was a lifesaver! I needed a cat sitter last minute and he promptly responded, went to see my cat, fed her, played with her, and sent me pictures. Thank you Chris!”


“Mikayla and Justin are simply great. They took great care of my dog Thelma, who can be very skiddish as she is a rescue. Mikayla and Justin spent ample time letting Thelma warm up to them before taking her out for a walk. I would 10/10 recommend them for any pet care and I will definitely be booking them again for Thelma!”


About: **Moving Out of New Haven end of June 2026** I've been a cat mom for 5+ years and a dog aunt for 6+ years. Earning a cat's love and a dog's cuddle are both incredibly rewarding experiences that I've been blessed with many times. I hope to experience such love with your loved ones! I am currently unemployed so Monday through Friday is generally flexible besides a few commitments that are consistent each week. For weekends, I'm typically most flexible on Sundays. I typically start my days at 8am and end around 8pm but again, the hours are flexible- please just reach out! I'm a homebody so to get some fresh air, I run around downtown New Haven 3x a week for 2-3 miles (generally Mon, Wed, & Fri). On days I don't run, I go on 5-10min walks. When I'm not job hunting, I am either baking bread, knitting, or watching anime. I am unavailable on: Mondays & Wednesdays after 6PM, Tuesdays between 5-7PM, Fridays between 4PM-7:30PM Most Saturdays (family & partner visit often!) I like to meet every cat/dog parent(s) beforehand, even if it is just for a few minutes. This helps me understand what is expected of me as the caretaker and if there is anything for me to be aware of. For example, I have a fur nephew who eats anything so he has to walk with a muzzle and I've had a fur niece who takes specific medications at different times of the day. I also always love seeing the parents with their loved ones because it gives me an idea of what type of interactions I'd be having with their loved ones. I care about cleanliness and will make sure the home is left exactly how you leave it. I also respect any dietary restrictions if there are any in the household. Lastly, as a cat mom herself, I care about receiving communication from those who are taking care of my beloved, so I enjoy updating parents with photos and how their loved ones are doing. Please let me know if this is something you'd like me to do!

About: What sets me apart from other sitters is my strong background in animal health and professional husbandry. Through my experience shadowing veterinarians, I’ve developed a trained eye for animal behavior and wellness. I know how to recognize the subtle signs of when a pet is feeling "off" or needs extra attention. I also have professional husbandry experience working with mice in a laboratory setting. This background means I am incredibly detail-oriented, strictly adhere to feeding and medication schedules, maintain rigorous hygiene protocols, and have a gentle touch with delicate or timid animals. I currently work remote for Yale as a PhD student, which allows me a great deal of flexibility to prioritize your pet's needs. On weekdays, I am fully available except maybe a few hours throughout the week for walks, playtime, and feedings. My weekends are completely open for overnight boarding, ensuring your pup is never left alone for long periods and receives constant companionship and care. My home is a 'pet-first' environment where safety and mental stimulation go hand-in-hand. For my two cats, I maintain a strict vertical-space setup and regular 'puzzle feeding' to keep them engaged. I am highly experienced in managing slow introductions and reading subtle body language to ensure all animals feel secure. I maintain a chemical-free cleaning routine to protect sensitive paws and noses, and I’m diligent about 'double-door' safety to prevent escapes. Whether it's ensuring fresh water fountains are clean or providing a quiet, crate-ready retreat, I treat every guest with the same meticulous care I give my own cats.
Wooster Square pet parents share their Rover experiences
Sarah has been taking care of my kitties whenever I’m out of town for the past year, and I couldn’t be happier with her care. She is kind, thoughtful, and attentive, and her notes are always detailed and reassuring. I feel completely at ease knowing my cats are being so well cared for while I’m away. I recommend her 100%!

Sara is very attentive and conscientious which makes her trustworthy. She was flexible in scheduling to meet everybody's needs. She took really good care of my cat. I could tell, because when my cat has had a good sitter, she is glad to see me when I get home but not frantic for my attention. Finally, Sara got my cat to play in a way I haven't been able to do (and still can't!) which goes to show that she is a true cat person. (I'm sure she takes good care of dogs, too.) I recommend Sara without hesitation.

Christopher did a fantastic job taking care of Boomer over the past two days. He was reliable, communicative, and clearly cared about making sure Boomer was comfortable and happy. I really appreciated the updates and the attention he gave throughout the stay. I’d absolutely recommend Christopher to anyone looking for a trustworthy and attentive dog sitter!

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1. Search
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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
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Why Choose Rover?
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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.
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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 Wooster Square.
Rover makes it easy to find Wooster Square 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.


















