Dog Sitting Winchester

“Very good with the cat!”

Lloyd E.

“Samichya and her husband were fantastic caretakers for my two beagles. They were wonderfully communicative throughout the stay, always quick to respond, and I felt completely at ease knowing my dogs were in such good hands. I came home to happy pups and a house left in great shape. Highly recommend their care.”

Nicholas W.

“This was our second time booking with Caitlin to watch our two kitties and everything went great once again! We were gone for over a week, but I think they barely missed us at all. Caitlin pays very close attention to each kitty and our skittish guy was out and hanging out with her within the first couple days! We were very at ease while we were gone, knowing Caitlin was taking great care of them - we will definitely try to book with her for our next trip!”

Alyssa B.

“Alexa was great with my dog. She gave me updates and sent me a pic. I’d happily hire her again”

Kat E.

“Veronica is such a sweet caretaker. My dog is pretty anxious but Veronica handles her with so much patience and grace. I can tell she’s an awesome dog mom who is understanding and loving towards other dogs. She’s a great communicator as well!”

Sarah K.

“Maia was wonderful with our beagles. She was very responsive and sent lots of photos.”

Nicholas W.

“Jillian took great care of my cats while I was out of town. She took extra time to make sure my cat was OK after he ate too quickly and vomited his food, and reached out to offer extra assistance if he needed it. I will definitely rebook with her the next time I need a cat sitter.”

Melissa W.

“Nina is a real professional who took very good care of our dog, Ceci. This is our first time working with Nina and she has earned our trust. Our dog requires a very specific and somewhat complicated routine for her diet and medication, which Nina administered perfectly. Just as important, Nina worked flexibly with our house-sitter to be there on time as planned for walks and exercise in the yard.”

Kate H.

“I was super happy with the support we received from Alissa! From the start, she was very responsive and helped answer my questions about the process/next steps. We had her stop by and watch our cat for 30 minutes over 3 days. She was great with our cat and we'd certainly work with her again!”

Ellen T.

About: I’m a lifelong animal lover and proud dog mom to a very loved (and very spoiled!) fur baby who currently lives with my mom. I truly believe our pets are family, and I’ll treat your dog with the same love, patience, and attention I give my own. Think of me as your pup’s favorite auntie while you’re away! Whether they need an extra-long walk, lots of playtime, belly rubs, couch snuggles, or simply someone to keep them company, I’m happy to follow whatever makes them feel safe, comfortable, happy, and loved. I also know every dog has their own adorable little quirks and routines—and no request is too small. If your pup needs you to pretend to microwave their food before they’ll eat it, I’m happy to do that. 😂 If they have a specific walking route, favorite toy, treat ritual, bedtime routine, or require an unreasonable amount of snuggles, tell me everything! At the end of the day, I want your fur baby to feel like they’re being cared for by family. I have a flexible schedule and plenty of time to give your fur baby the attention they deserve. I’m available throughout the week for walks, drop-ins, playtime, and quality time. Whether your pup loves long walks or prefers a slower stroll with plenty of sniffing stops, I’m happy to work around their routine and needs. Your pet’s safety, comfort, and happiness are always my priority. I’ll care for your fur baby as I would my own and follow your instructions closely—from feeding and walking routines to medications, favorite toys, and all their little quirks. I also like to have your preferred veterinarian’s information and an emergency contact on hand, just in case. God forbid anything happens, I want to know exactly who to contact and where you would want your fur baby taken. I’m respectful of your home, attentive to your pet’s behavior, and will always do my best to make sure they feel safe, loved, and comfortable while you’re away.

About: I am a freelance artist by trade, I'm looking to earn some supplementary by putting to good use my love of animals and experience as a lifetime pet owner. I have been the primary caretaker for animals basically my whole life, growing up alongside furry siblings as long as I can reliably remember, including several dogs with behavioral issues such as separation anxiety and jealousy problems. My mother trained as a vet tech and taught me a lot, and is always happy to help even now if I need an extra hand or some expert advice. I have trained dogs, including potty training and dissuading problem behaviors (excessive barking, begging for food, etc.) I have experience caring for dogs in individual, group, and playgroup settings and love all animals. I cannot drive but I can engage in light to moderate dog walking just fine! I use public transport and ridesharing to get around. If you have any further questions about what might be within my wheelhouse feel more than free to ask! As a freelance artist, my schedule for work is fairly flexible and I can plan around pet care time and stays away from home with a lot of freedom, making it possible for me to keep my schedule fluid and make the animal in my care the priority of my routine. I have an apartment in Arlington I spend most of my time at but it's not the best for pets so for boarding jobs I visit and make use of my parents home in Winchester. They and their dog love the company! It has a fenced outdoor area where dogs can easily run, play, and of course go to the bathroom. It is accessible via a basement door and most dogs get the hang of it pretty easily (but I am happy to provide extra help for dogs who struggle with stairs or need other extra accomodations.) It is also home to my parents who love furry guests, and of course Emma, an extremely friendly and patient English Setter who adores playing hostess! I am also of course happy to visit other homes to care for pets, both for drop ins and overnight. I will always take the safety and cleanliness of your home seriously! In other's homes I'm happy to adapt to what resources are available and what areas and routines the dog is generally used to and comfortable with in their own usual environment!

“Elisangela was great with watching my two cats while I was away on vacation. She dropped in on the dates and times as discussed, sent plenty of updates and pictures. Would highly recommend!”

Kristen G.

“Hillary was a great find in the "eleventh hour" of my search for service. She dropped in and took really good care of my dog while I was far away for the day. I felt confident from our first texts and Hillary's generous effort to come to my home for a meet n greet. Hillary followed through with great communication, lots of photos and follow up texts. I would call her again in a heartbeat and highly recommend her services ! Thank you so much!”

Christine S.

“Michelle is amazing with our three senior dogs. One is deaf, one is stubborn, and one is very excitable, so it’s definitely not an easy group to manage. She handled them all with patience and care, and after her first visit we felt completely comfortable.”

M.J F.

“Sasha did an absolutely wonderful job with my kitties during my first trip out of town! She was easy to reach and work with, learned each of my pets’ individual needs and personalities, and kept them happy and entertained. She sent tons of cute pics and updates and when one of them had a minor vomit-sesh, she cleaned up no worries and just let me know after. Totally recommend her services!”

Meredith M.

“Sarah was wonderful with my pup Penny! Penny is used to pretty much always being by my side, and she was (unexpectedly) scared when I wasn't there. Sarah and her son took the time to coax Penny out from the under the bed and made her comfortable for future stop ins. As a pet parent, I felt much better knowing that my dog was both happier and in great hands! A very positive experience!”

Gretchen H.

About: Although I don’t have the most experience, I played a large part in the raising and training of my friend’s dog when he was just a puppy in this past year. I treated him as one of my own, and I will do the same with your pet! I am a full-time PT student looking to earn some money on the side and I am available to play with your pets during my spare time. I usually have classes until 5 pm on weekdays and free on most weekends so my schedule can accommodate! I will always prioritize your pet’s safety and treat them as if they were one of my own. I will take this responsibility very seriously and always model my services based on your instructions.

About: For the last two and a half years I have been taking care and walking my families dog, and the amount of love and care she needs makes me even more eager to help out whenever needed because dogs and in general pets are a humans real companion. I have also recently took care my family friends two tall and fluffy poodles and it was the best 10 days of my life. I am a full time student, and have another part time job. I am very willing to walk your dog after school. I am also willing to wake up very early (about 6 am) to walk pets right before school starts. My weekends are often free and most times I’ll be available on every second weekend of the month after 5:30 pm. I unfortunately cannot have pets in the apartment I am living in currently. I would be very happy to get familiar with one’s home and see what also the dog’s needs may be and I’m willing to adjust to whatever a pet may need.

“Kim and Kenn are wonderful cat sitters for our cat Casper. We loved their updates and feel very comforted by their care for our beloved cat when we are traveling.”

Saskia H.

“Lindsey was great with my two pups. Twila is only 6-months-old and she's quite shy, while my other dog Chester is just over two-years-old. I had Lindsey do check ins the first week we got Twila as I was adjusting my work hours to accommodate a new puppy. Lindsey was timely, caring and patient with both of my dogs. I highly recommend her!”

Taylor L.