Dog Walking Winchester

“How do I even begin. James came into our world when our rescue senior needed walks throughout the day. For 5 months he made her feel loved and safe everyday. I would trust James with anyone and any pet. Besides his overwhelmingly empathetic presence, James is also reliable, prompt, and an amazing communicator. No matter the day, time, weather, etc, we knew we could always count on James. I truly could not recommend him enough”

Helen H.

“Noila was wonderful, she stepped in at the last minute to walk my dog who had gotten sick and needed to be checked on. She was super responsive to changes to the schedule and was prompt with the walk.”

Molly L.

“Hannah is definitely the best walker I have ever met. She is so responsive and sweet, always having a safe and happy walking journey with my doggy. I will always go back to her.”

Liu Y.

“Angela is great with our pup! She has great communication and our pup is always so happy to see her. Angela always lets us know what’s going on and wants to know how we are training so everything is consistent.”

Thomas S.

About: I absolutely love dogs! I’ve had large dogs all my life, have pet-sat for many friends and neighbors, and have fostered 15+ rescue dogs for Last Hope K9 Rescue. I am also a dog training enthusiast, and have been training my Australian Shepherd for obedience and agility for the past 6 years. I recently interned with a local veterinarian, handling all sorts of pets including dogs, cats, and rabbits. I live right near the Middlesex Fells Reservation, and love bringing canine friends along on Fells adventures! I am home all day all summer, with lots of time on my hands to play with pups, take them on hikes, and give them all the attention they deserve! I am 18, and I live with my parents and sister (16). I have a fully fenced yard. It is accessible to the neighbors' two friendly dogs who often come over to play, but the yard can be closed off as necessary. I have a 6 year old Australian Shepherd who loves other dogs, but he usually keeps to himself when they stay over.

About: My name is Jhonatan (but you can call me Jay) and I would love to take care of your best furrriend. I’m a 31 years old Brazilian folk that works with art so I have plenty of free time on my daily basis. I was raised with 4 dogs in Brazil, but unfortunately don’t own one. I have more than 10 years of experience in dog walking, pet sitting and pet boarding. I’m a makeup artist that has a side job as freelancer for selling makeup products but trying to work with pets more after a year of not doing so. I used to dog walk and pet sit by myself but stopped after some health issues (I’m healed now) and I’m trying to do only on Rover. I’ve signed up a few years back and did only one sitting but deleted the app. I know CPR and First Aid for pets so your best friend would be safe in my hands (if any natural incident ever comes to happen). I have experience with bigger (such as Great Dane) and smaller dogs (chihuahua), with elderly and puppies (as well as how to better train their behavior), with aggressive and non aggressive dogs, I’ve split fights before and also know some how to teach your dog to behave and walk better outside with other dogs. I used to work for a dog trainer and have learned some things that could help them. I’m currently working part time free lance for makeup brands and make my own schedule so I’d have plenty of time to spend with your furrriend. If I’m pet sitting I usually would make my schedule in a way that I’d have time to walk the dog a few hours a day, twice or 3 times a day and sleep with them. If dog walking I’d walk them for 30min, if allowed I’d love to bring them to a leashed hike if nearby. I always try to keep myself calm because from all years working with dogs it shows that they feed off people’s energy, I practice yoga and meditation so that way it helps to keep them calm and relaxed. In your home I’d feed and give them water, have them exercise so they spend their energy and they can have a nice sleep. On walks I give them water breaks if too hot and always watch for their behavior.

“Brooke was super prompt and communicative. I appreciated the information she shared about how the dog walk went, including photos. She was available on very short notice, which was extremely helpful.”

Samuel G.

“Thanks for a great walk in the snow! Atlas seemed to have a fun time :)”

Stephanie R.

“Tanya took such good care of Poppy! Poppy loved to see her come and happily went on the walks to roll in the grass and smell every little thing! Tanya had patience! Poppy will miss her!!!”

William T.

“Katiana was excellent, after she visits for dog care everything is exactly how it was left and the dog seemed great after I returned home. Katiana sent schedule updates and photos and summaries of her visits which was also appreciated”

Colin D.

“Super helpful in a pinch, made friends with my doggo really fast, and tired out my very energetic doggo. Great pictures, nice updates.”

Kit H.

About: What sets me apart from other sitters is my deep compassion, patience, and experience with dogs who need extra attention—especially those with anxiety or special routines. I have hands-on experience caring for senior dogs, puppies, and pets who struggle with separation anxiety. My own dog, Sasha, has anxiety, so I understand the importance of gentle care, consistency, and emotional support. I treat every pet like family, and I’m committed to creating a calm, safe, and loving environment while you’re away. Whether your pup needs long walks, slow introductions, or just a cozy lap to nap on—I’ve got you covered! Pet care fits naturally into my weekly routine. I have Mondays and Tuesdays off, which gives me plenty of time for daytime walks and drop-ins. On other days, I’m able to fit in visits between school and work—and I don’t mind doing late-night drop-ins if your pet needs evening attention. Caring for animals is something I truly enjoy, so I’m happy to make it a priority in my schedule. I’m dependable, flexible, and always focused on making pets feel safe and loved while you’re away. I only offer pet care in the client’s home because I believe pets are happiest and most comfortable in their own familiar environment. I follow your pet’s routine closely—whether that’s feeding, walks, playtime, or administering medication. I respect your space, keep things tidy, and make sure your pet feels safe, loved, and cared for while you’re away. My goal is always to provide reliable, stress-free care that gives both you and your pet peace of mind.

“Stacey is an amazing walker who took her time to make our dog feel comfortable with her! She walked him, played with him and gave sweet and funny updates too :)”

Katya E.

About: I have had a family dog for over 10 years now and have taken care of her all her life. My own dog now lives in New Hampshire, but I still would love to take care of and play with dogs on a daily basis. I have also watched friend’s, neighbors, and other family members dogs all my life and enjoy every second of it. I am currently on summer break from attending college in New Jersey. I will be in Massachusetts until September and am available every weekday full time for the next 10 weeks to be able to devote my time and care for your dog. My home includes an outdoor deck that leads to a fenced in backyard that is perfect for dogs to be let out and taken outside to use the bathroom or play on the lawn. Also, I have my dogs older bed, toys, food, and treats from before she moved to New Hampshire. My bedroom is also very close to the door leading to the deck, so letting dogs out to use the bathroom in the night is quick and easy. There are stairs leading up the the home but I can easily pick up dogs that may not be able to climb them.

“Kathryne was very responsive and took great care of Zoey. We look forward to seeing her again for another walk!”

Traci K.

“Awesome first walk today. My pup is a little timid and not used to having strangers in her space. Rebecca was incredibly patient with Penny and really focused on creating a bond with her which is so so important. By the end of the visit Penny was eating treats out of her hand, licking her face, and welcomed Rebecca’s cuddles. I couldn’t believe she was able to win Penny over so quickly. Couldn’t be happier!”

Treasure B.

About: Spent extensive time caring after my families dogs & cats as well as the pets of my neighborhood. I also look after my friends cats and dogs of Boston and Maine. Comfortable with walking, playing with, feeding, and even some light training with dogs. I don’t have certifications with dog training but I would be happy to reinforce training you do with them for some light commands. I work in sales in a fairly fluid environment. I spend some time at home and the rest of my time around the city and greater Boston. Drop in pet care/walking fits perfectly into my schedule as I can work from my computer and travel when needed. I do have a fenced in yard but I’m not currently accepting pet care in my own home outside of the critters I already have. I may open up to this in the future but I do use a lot of space In my car already.

“Ryan is great and both an excitement and a comfort to our large (sometimes anxious) dog. So great to make sure our pup has the exercise she needs even when we aren’t able to provide it personally. Not only would I hire Ryan again, I have and plan to do so in the future!”

Rachel O.

“The most supportive and compassionate dog walker , she came right in with my pup who struggles with basic commands and started teaching her and then took her on her first walk and she didnt even pull her because Cheryl is very confident and firm. Im booking her again today! Thank you so much”

Lindsey C.

“Sarah was great! Very responsive and thorough. Would definitely book her services again 😊”

Charlotte M.