Dog Walking in Winchester

“Shawn is wonderful with our girl Apple! She is so kind, patient, and very trustworthy - we all immediately liked her and are so grateful that she can help us with our pup 😊”

Kevin L.

“Cheryl has an amazing heart! I can’t say enough good things about her, she always helps me out even on last minute walks. She is phenomenal with updates and it’s super attentive. Highly recommended. Kratos loves her.”

Cindy G.

“Very professional, thoughtful and thorough services! I was very happy that I was able to leave my dog home without any worry and he was taken care of very well! Parker (although not into people much) seemed to really like James's energy and went out with him no problem. I hope we will be able to use James' services in the future.”

Petra L.

“Olivia was great! She communicated well which is key! She took Cindy for a nice walk and sent us photos so we new she was getting attention while we were away. Would love to have her again!”

Kimm & Kenn S.

“Noila was very prompt and walked Miles without any issues. She had a last minute adjustment close to the time and had to modify the booking, but she was very apologetic and professional about it. We would definitely use Noila’s services again.”

Maple G.

“A caring, friendly dog walker you can trust!”

Will C.

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

Charlotte M.

About: I have been around animals all my life. Grew up in the rural Midwest surrounded by dogs, cats, rabbits, hamsters, turtles, in addition to the cows, pigs, chickens, and horses at nearby farms. I love animals and have helped care for them all my life. I am comfortable with all kinds and sizes of dogs and love getting them out on walks/hikes and playing with them, snuggling with them indoors as well. I adore dogs and remain calm, letting them get used to me before trying to engage...letting them set the stage or lead the way. Once I get to know them I am very affectionate with them and love to play and run around with them. I currently live in my own place with my cat and would love to care for your pets in your home. I'm currently between jobs and thought I would get back to pet sitting/walking for now. I love hanging with my furry friends and getting out for brisk walks! I will spend time getting to know your pet, snuggling with them(if they want), getting them outdoors and playing with them, keeping them on their feeding schedule and caring for them like they're my own.

“Angela has been a lifesaver. She was quick to respond when we needed a last minute, recurring walker and worked around our hectic schedule for a meet and greet. Our two labs absolutely love her and look forward to their morning walks. She’s communicative and considerate and I also look forward to seeing her in the mornings as she has a great personality! She’s a pleasure to work with and we are lucky to have found her. Highly recommend!”

Catherine S.

“Sarah did a wonderful job.. she clearly loves dogs and is very good with dogs. My pup was so comfortable with her. Definitely recommend Sarah.”

Ann G.

“Thanks so much Caroline for taking such good care of our two dogs while we were away - you were a lifesaver! Highly recommended - will certainly use her again!”

Robert C.

“Rebecca is a rockstar!! Super responsive and quick with communicating, friendly, and accommodating. She clearly loves taking care of dogs and making sure they’re attended to.”

Nuri J.

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.

“Extremely dependable and arrives exactly when promised - she was so prepared that she even brought towels to dry off the dogs when it was very wet outside! Thanks again!”

Jonathan L.

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.

About: Since age 12, I’ve cared for dogs and cats for family, friends, and neighbors—walking, feeding, and overnight sitting. It’s truly one of my favorite things. I work from home on Mondays and am available weekends, making pet care flexible and convenient. I’m highly responsive, adaptable, and will love your pets like my own—whether for walks, check-ins, or extra attention. In my home, pets are fed breakfast early each morning between 7-9am and supper around 5 pm. My dog enjoys multiple daily walks, while my cats lounge in sunny windows. Litter boxes are scooped often, and I keep their space clean and comfortable. In a client’s home, I’m happy to follow any instructions provided—whatever keeps their pets happiest and most at ease.

“Allie has been so great for my bichon poodle Zuri. Zuri is a very leash reactive dog who also tugs during walks. Allie has not only handled these issues patiently (she has tons of experience with pets!) but also has contributed to Zuri being better behaved on walks! On days when Allie doesn’t come, Zuri waits by the door at her usual walk time for her new friend. Allie is also very punctual and has always been accommodating of my last minute changes. Above all, Allie is extremely kind and sweet. I know Zuri enjoys her walks and loves Allie.”

Darleny R.

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

Traci K.

“Sanela was wonderful. Came last minute and was very nice, friendly and most importantly, my dog loved her. Will definitely use again. This was my very first Rover experience and I was bit nervous, but it went better than I could have expected thanks to Sanela.”

Kimberly H.

About: I've always loved taking care of dogs! I had my first when I was 9, a beagle. Throughout the years I've done various dog-walking and dog/cat sitting for friends and family, and now I miss seeing all the dogs as I live away from them and they have passed :'( On multiple occasions, I took care of two loving but rambunctious pit bulls for weekends and extended periods of time while my friend was away. Gave them medicines, lots of attention, and invigorating walks. I took care of the house while they were away and sometimes stayed overnight. I have experience with dogs that need to be on a tight leash in certain scenarios, and experience allowing them to just have fun in safe spaces. With well-behaved dogs, I've gone on runs in the forest and been able to have them off-leash. I love having a buddy! I care a lot about maintaining the boundaries and rules around how you have trained your pet and keeping their routines. I manage an office nearby Monday thru Thursday, flexible Fridays. The morning walks are reliable and I can message you specifics and sort your dog’s and my schedule around it :) Most days, the afternoon walk can be configured into the schedule. We have a larger yard and no pets living in the house. My sisters nearby both have friendly dogs if yours would like some pals. Some days are busier or have a tighter walk schedule for me, but usually just 2 weekdays, which is why this works for me! I love taking dogs to different adventures like the Fells or games in my backyard, or just hanging out and cuddling :)