Dog Sitting Winchester

“We recently moved to a new apt and needed a new sitter for our 10 year old kitty. Carol did a great job with her in all ways. Carol kept her routine and spoiled her the way we do. Our cat was relaxed and well taken care of by Carol. Highly recommend her pet services.”

Linda K.

“Angela took great care of our dog during a weekend away. She is an excellent communicator and sent lots of pictures too keep us posted of drop ins and walks. Would definitely ask her to help us out next time we need to go out of town.”

Rajani G.

About: I adopted my first dog in second grade. He was my responsibility and as I got older, I learned that I loved going for walks outside as much as my dog. Now that I'm older, I love taking friends' dogs for hikes in new locations. I have even managed to train one of my friend's reactive dog so she pulls on the leash less. I also briefly fostered animals when I was in graduate school. I am a teacher on summer break, so I have plenty of hours to devote to your pet and look forward to enjoying plenty of summer outside time with your dog. I have walked a wide range of dogs, including a couple of reactive pit bull mixes. I have experienced triggering situations with dogs and know how to either handle them or avoid them.

“Caitlin tended to my sweet cat like a pro! She kept Darla’s many mugs filled with fresh water and Darla’s belly appropriately filled with plenty of treats. I get apprehensive leaving Darla behind given her tendency toward constipation… however Caitlin handled even that turbulence with compassion and creativity. 10/10 would book again!”

Kelsey M.

About: Animals have been part of my life for as long as I can remember. I grew up surrounded by dogs, cats, birds, fish, turtles, hamsters, gerbils, and even chickens, and each one taught me something different about patience, joy, and unconditional love. Over the years, I’ve rescued dogs, helped others find their forever homes, and volunteered at shelters and adoption events. I have a soft spot for senior pets and pups with special needs. My dog Dumba is turning 16 this February, and supporting her through her golden years has taught me how to be gentle, attentive, and adaptable. Before Dumba, my dog Cookies bravely fought cancer for many months, and I cared for him through two surgeries and ongoing treatment. Because of experiences like these, I’m comfortable administering medication, monitoring health changes, and giving extra support to pets who need a little more care. I also love working with cats! Since rescuing Zoro when he was only 8 weeks old, I have developed experience with basic grooming, brushing, and keeping litter areas clean and comfortable. Your pets are family, and I’ll care for them with the same love, patience, and attention I give my own. My schedule is flexible, and I’m happy to accommodate your pet’s routine. I'm currently offering daily walks and drop‑in services. I live in Winchester and know the area well, so your dog can enjoy peaceful walks around Horn Pond or fun playtime at Sheepfold Dog Park. I share my home with my senior dog, Dumba, and my goofy cat, Zoro. They’re both used to being around other animals, but my space isn’t large enough to comfortably or safely host additional pets. Because of that, I offer care exclusively in your home, where your pet feels most secure and where their routine stays consistent. When I’m caring for your pet, I follow your house rules and make sure your pet’s environment stays familiar and stress free. My goal is to respect your home, maintain your pet’s routine, and give them attentive, loving care while you’re away.

“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.

“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.

“Jillian is wonderful and I will continue to have her taking care of my little guy!!”

Brian S.

“Kathryne took excellent care of our 2 dogs and at last-minute notice! She was very responsive to messages and flexible when there was a slight schedule change. Would not hesitate to book again!”

Kira S.

“Nina was a fabulous drop in for my cat. She took great care of him, adapting to his needs, and managing the litter box, trash, and recycling. She even carefully cleaned up after him when he had a digestive glitch as cats sometimes do, without complaint and with genuine concern for his well being. Drop in photos were a delight and made me feel he was happy and comfortable. I trust her and will definitely book her again.”

Alex N.

About: I’ve been pet sitting and dog walking for about 7 years. I have experience watching dogs of all sizes and I just love being around them! I am currently a junior in college on summer break and working part time - mostly nights - so I’m usually available during the afternoon. I love walking so I’m able to walk your dog in your neighborhood, or I’m willing to take the dog to your yard to play, whatever you prefer.

About: I’ve been around dogs my entire life and have experience caring for pets for family, friends, and neighbors. As a retired Division I student-athlete and current graduate student at Tufts, I am dependable, responsible, and highly organized. I understand that pets are family, and I treat every dog as if they were my own. One thing that sets me apart is my patience and ability to adapt to each dog’s unique personality. I have experience working with anxious, timid, and shy dogs who need extra reassurance, as well as high-energy dogs who thrive with exercise, structure, and play. As a former Division I athlete, I am also comfortable handling larger, stronger dogs and can confidently keep up with dogs that need long walks, runs, or plenty of activity. Whether your dog needs exercise, playtime, lots of attention, or simply a reliable person to check in on them, I’m happy to help. Your pet’s safety, comfort, and happiness will always be my top priorities. I also provide regular updates and photos so you can have peace of mind while you’re away. I’m a graduate student at Tufts University with a flexible schedule that allows me to provide reliable pet care throughout the week. I enjoy staying active and spending time outdoors, so dog walks fit naturally into my daily routine. Whether your pet needs a quick potty break, a long walk, or a drop in visit, I’m committed to being dependable, punctual, and responsive. Your pet’s safety and comfort are my top priorities. I take the time to learn each pet’s routine, personality, and specific needs so they feel secure and cared for while you’re away. I will always follow your instructions closely, keep pets safely leashed during walks, and provide regular updates and photos for peace of mind. I treat every home with respect and every pet as if they were my own.

“Kat was great with Bella! Bella enjoyed the time that Kat spent with her. I enjoyed getting the pictures of Bella every time Kat came over while I was gone and seeing how happy Bella was! Thank you Kat for taking care of Bella and my mums!!!”

Abby B.

“Always a life saver! Elisangela has not only taken amazing care of our cat Rudy on several occasions, but worked with us on scheduling, rescheduling and stepping in last minute when we've needed help. Amazing and cannot recommend enough!”

Alison C.

About: For the past few years now I’ve been a dog sitter for my family and friends, walking, playing, feeding, and cleaning up after them I can house sit, dog walk, and do drop in visits, Any time of the day Mondays to Fridays, And weekends if needed anything works. I get to learn pets usually routine. How many times a day to walk them, when and how to feed them, and their bed time.

About: I’ve always loved dogs and cats 😊. I like to think I am very reliable and genuinely care. While I’m walking a dog I carry poop baggies, water and a water bowl, and a ball/toys. When I board dogs I use the same things. I’m open and flexible to accommodate whatever your dog or cat needs. I also of course am well versed in dog language so I’m able to know what your dog is trying to tell me. (I also know that the rates are high so I’m always willing to negotiate if you don’t want to pay the exact set price 😁.) I’m pretty flexible with time. I’m free after 4-5 weekdays and free all day on the weekends. For dog boarding there is always someone at my house for the part of the day I’m not there, (and she of course loves dogs 😁.) I have a nice big unfenced yard, and a small portion of the yard fenced. There are also lot of parks (Audubon) and tons of great paths to walk dogs in my area.

“Olivia did a great job caring for Santana and giving him his meds. She was a good communicator and went the extra mile to help us out on short notice.”

Libby H.

“As we just moved to a new place and did not find a cat sitter yet. After reading the positive reviews we decided to reach out to Kimm & Kenn S. Kimm has been such a treasure during our time away. From the get go she communicated very timely, clearly and really wanted to make sure she understood what we were looking for. Throughout our time away she kept us up to date on our cat's wellbeing. We are so happy she took care of our furry friend and will definitely reach out again in the future. Thank you, Kimm!”

Saskia H.

“Maria and her partner happily accepted a quick meet up before meeting Mochi and I. They were eager, friendly, and very respectful. They spent and hour each day playing, petting, chasing, and cuddling with Mochi. My little Mochi was ecstatic to see them and play with them. Knowing that she was in great, eager, and safe company and while providing her nonstop attention for the hour was the best I could ask for. Would love to have Maria and her partner hang with Mochi again soon!”

Christian S.

“Yuting was super easy to communicate with and extremely prompt on her reply (especially with myself needing the check-in about 40 minutes ahead of schedule). On top of that, I had complete peace of mind that she was the one checking in on my old man (cat), especially after reading her profile and a brief chat with her. Extremely happy she had availability for me, and definitely will be booking again!”

Ryan M.