Dog Walking in Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
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Top rated Winchester dog walkers
“Alina has been fantastic with our little boy, Linus! She walks him four times a week, always sends wonderful pictures, and is incredibly caring and attentive. I highly recommend her as a dog walker and sitter!”
“James was seriously the best!! So sweet and patient with Lilly, you can tell he really cares. We’ve worked with other people on Rover before, but no one like him. He always sent the nicest updates and the cutest pics after each walk, which we really appreciated. Felt so good knowing our baby was in such good hands. Thank you, James!! 💛🐾”
“Max is reliable and great with my dog Louie! He made sure Louie was comfortable with him prior to taking him on a walk and send me plenty of updates and pictures! I highly recommend Max!”
“Michelle walked our very nervous timid rescue boy Ollie and did a great job. She was persistent with him and got him outside for a walk even when he was nervous as he usually is with strangers. Overall we were satisfied with her services and would use her again if we ever need help.”
“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!”
About: I have taken care of my parent's dog since she was a puppy. I trained her to do basic and complex commands. I love spending time with dogs, discovering their personalities and what makes them special! I am working part time, and have plenty of time to take care of your dogs! Please feel free to reach out with any scheduling questions, and I am sure we can figure something out. My current apartment does not allow pets, so unfortunately I cannot do overnight board in my current home. However, I am great at walks and general day care.
About: Hi! I’m Kristin — professional treat-giver, belly-rub specialist, and lifelong animal whisperer. I’ve had pets my whole life (from dogs & cats, to fish & hedgehogs), and genuinely believe there’s no better company than a wagging tail. Dogs love me (and the feeling is VERY mutual)! From walks, playdates, socializing, or hanging out, I’m the kind of friend who sends cute updates, not just the basics. Whether you need a trusted pal to walk your pup, a reliable sitter to hold down the fort, or someone to spoil your pets like they’re royalty — I’ve got you. Bonus: I’m neat, punctual, and fully prepared to talk to give your dog new ridiculous nicknames. Let’s get those tails wagging! 🐶 If you don’t see availability that meets your needs, send me a message and see if we can coordinate! I currently have a very flexible schedule during the week so I can accommodate morning, lunch, and evening puppy dates. I'm looking forward to cuddling your pups! I treat every dog like they're my own! What does that mean? Lots of love and snuggles (and treats if they're allowed). I have no problem following any structure that you already have for your dog, or helping you create consistency for them.
About: I’m a dog person! I love meeting new dogs and spending time with them. I’ve taken care of dogs off and on for 20 years (not including my own). I currently have a rat terrier mix - Roxie - who LOVES dog friends and is very playful. I’m a big walker and have experience with dogs on trails as well as in neighborhoods. I’d take care of your dog like my own. Most of my experience is for extended stay house-sitting for families with multiple dogs. I’m not able to have cats in my apartment, but love meeting cats in their own space and would be sure they were well loved and taken care of in your absence. I work from home full-time and have a very flexible schedule which allows me to be available most times of the day. I can work around complicated calendars! I have a fenced yard and a VERY friendly rat-terrier mix named Roxie. For house sitting, Roxie can come with me or stay behind, but she’s great with dogs off all sizes and I’m very careful when bringing her into another dog’s space.
“Andew showed kindness and conscientiousness and respect to my elder shiba inu, while also holding the boundaries that these basal breeds need. Knowing that Andrew was walking Jaxson gave me the peace of mind to do the work in the world I am called to do. Gratitude.”
“So grateful for Caitlin! I work from home and was nervous about hiring a dog walker when I recently had to be in the office for a multi-day event. Caitlin took great care of my dog Summer and walked her for the full 30 min (sometimes a bit more!) I really appreciate trustworthy folks and it's a bonus that Summer seemed to really like Caitlin too.”
About: I have a special passion for animals. Whether you have a Chihuahua or Doberman, I have loved and cared for dogs of all sizes. I currently have a dog of my own(Lily), who I rescued when she was a about 3 months old. She was very sick then, and required extensive care from me. Now I can happily say she is a happy, healthy 8 year old. I am also caring for my family’s senior dog, who has the exact opposite needs of my own. Whether your dog is full of energy and needs to play, or needs a soothing cuddle on the couch, I can assure you I will take the time to find out how to bring them happiness. I typically will be available for pet care any day of the week and any time of the week. The exceptions will be known in advance and I will block those days/times on my calendar. While I care for your pets in your home I will be sure to keep them entertained. I understand many pets have separation anxiety, and I am very familiar with that, as my own dog deals with this. Although I can’t replace you I want to make sure your dog still knows they’re safe and that “mommy” or “daddy” will be home soon.
“Natalie was very quick to respond to me last minute! I was worried about having someone come walk the dog who I haven’t met before but she did a great job making me feel comfortable with lots of pictures of my dog on their walk and took excellent care of her. Would absolutely recommend her as someone you can trust to take great care of your pets! Thanks again, Natalie!”
About: Master's degree in animal care and welfare. Former vet tech for dogs and cats at an E.R. I also have an Animal Science degree and have cared for horses and other animals. I work from home some days, part-time, and always have walk breaks. I go for long walks and will join with doggy playmates if your dog is able. Will also walk small dogs in carriages for fresh air. Have fenced in yard for small and medium size dogs. I have a fenced in yard and one Bichon rescue dog who is older, and friendly with other dogs. I was a former vet tech and have much cat and dog health care skills.
“Erin is super reliable & sweet with my dog Walter who she takes on walks frequently for me when I’m away. She always giving him treats and is so good w him. Thanks Erin!!”
About: I love dogs as long as I can remember. I had my first best friend when I was four and I named her Crazy. Then I had Crazy II, Cuquita, Shadow and Roxy. I have dog sit for families in Winchester and Lexington, MA (I can give you references). I love to go for long walks, play and stay at home with your best buddy and give tons of love while you are gone. I could send pictures of our adventures and keep you posted about his/her daily routine. You might be surprise when start listening to him/her barking in Spanish ;) I believe that dogs & babies understand multiple languages, so I'd speak in English and Spanish. Guau Guau! Woof Woof! Hope you like the idea... Alma
Loving dog walkers in your neighborhood
Search Results
Alina M.Star Sitter
“Alina has been fantastic with our little boy, Linus! She walks him four times a week, always sends wonderful pictures, and is incredibly caring and attentive. I highly recommend her as a dog walker and sitter!”
James T.Star Sitter
“James was seriously the best!! So sweet and patient with Lilly, you can tell he really cares. We’ve worked with other people on Rover before, but no one like him. He always sent the nicest updates and the cutest pics after each walk, which we really appreciated. Felt so good knowing our baby was in such good hands. Thank you, James!! 💛🐾”
Zijia C.Star Sitter
“Max is reliable and great with my dog Louie! He made sure Louie was comfortable with him prior to taking him on a walk and send me plenty of updates and pictures! I highly recommend Max!”
Michelle T.
“Michelle walked our very nervous timid rescue boy Ollie and did a great job. She was persistent with him and got him outside for a walk even when he was nervous as he usually is with strangers. Overall we were satisfied with her services and would use her again if we ever need help.”
Angela R.
“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!”
Malia B.
“Malia is a fantastic and caring person! She has been a friend for over a decade and has never failed me. She has been the one to step up and take care of and help train her family dog for the past couple of years. Ona, her dog, is impeccably trained and so well loved, she is tied to Malia's hip when she's back home. Trust that Malia will provide the best care for your dog and give them the love they deserve.”
Blane H.
Star Sitter
“Blane was amazing with Frankie!! She’s definitely particular and he was great with sending updates and making sure she had a great time on her walks!”
Shawn V.Star Sitter
“Wow, Shawn is AMAZING! Great with our pups. Prompt and very professional communication. Can’t say enough great things about her. Will absolutely work with her again!”
Kristin C.
“Kristin is incredible with my pups! I have a very anxious husky and a little yorkie with major napoleon syndrome, and she’s handled them like a champ! I had a family emergency and Kristin was able to help me out while I was out of the country with no problem. I genuinely could not recommend someone more; Kristin really treats my dogs like her own and my kiddos love her! The amount of pictures and updates during the day made me know they were in good hands!”
Annmarie M.
“I highly recommend Annmarie as a dog walker and sitter. She took excellent care of my senior dog, Moose, both on daily walks and while I was away traveling. Moose could be a bit particular in his older age, but Annmarie was always patient, attentive, and gentle with him. I had complete peace of mind knowing he was in her care. I'm adopting a new dog next month, and Annmarie was the first person I contacted to help with walks. I trust her completely and know she'll be just as wonderful with Willa as she was with Moose.”
Andrew K.Star Sitter
“Andew showed kindness and conscientiousness and respect to my elder shiba inu, while also holding the boundaries that these basal breeds need. Knowing that Andrew was walking Jaxson gave me the peace of mind to do the work in the world I am called to do. Gratitude.”
Rebecca S.
“Stupendous! Burkus was happy to see her new friend Rebecca and go on a long walk with her. Love the photos so good to see her while I’m at work.”
Caitlin M.Star Sitter
“So grateful for Caitlin! I work from home and was nervous about hiring a dog walker when I recently had to be in the office for a multi-day event. Caitlin took great care of my dog Summer and walked her for the full 30 min (sometimes a bit more!) I really appreciate trustworthy folks and it's a bonus that Summer seemed to really like Caitlin too.”
Sarah M.
“Sarah has always been loving caregiver to our dogs since2001. She loves to play with them,cuddles them .Right now we have an older dog and she is great with her. I would highly recommend her for dog walking or just playing with or cuddling them or anything else your animal may need.”
Natalie J.Star Sitter
“Natalie was very quick to respond to me last minute! I was worried about having someone come walk the dog who I haven’t met before but she did a great job making me feel comfortable with lots of pictures of my dog on their walk and took excellent care of her. Would absolutely recommend her as someone you can trust to take great care of your pets! Thanks again, Natalie!”
marilyn g.
“Hi, I am a dog and cat Mom, I have had Marilyn watch all my pets for many years. What I think sets Marilyn apart from other sitters I have had is her experience as a veterinary technician. She has been such a huge help with some of my medically complicated or geriatric pets over the years! She goes the extra mile to make sure they get the care they need. I’m so thankful we have her!”
Erin F.Star Sitter
“Erin is super reliable & sweet with my dog Walter who she takes on walks frequently for me when I’m away. She always giving him treats and is so good w him. Thanks Erin!!”
Courtney R.Star Sitter
“Courtney walked our pup all week. She was super reliable and Muri really seemed to enjoy her. Thanks Courtney!”
Kelly D.
“I was impressed that the first walk without prior introduction went smoothly. Chip seemed relaxed and happy. Kelly sent me pictures too, which was reassuring”
Alma M.
About: I love dogs as long as I can remember. I had my first best friend when I was four and I named her Crazy. Then I had Crazy II, Cuquita, Shadow and Roxy. I have dog sit for families in Winchester and Lexington, MA (I can give you references). I love to go for long walks, play and stay at home with your best buddy and give tons of love while you are gone. I could send pictures of our adventures and keep you posted about his/her daily routine. You might be surprise when start listening to him/her barking in Spanish ;) I believe that dogs & babies understand multiple languages, so I'd speak in English and Spanish. Guau Guau! Woof Woof! Hope you like the idea... Alma
How Rover works
1. Search
Read verified reviews and choose a dog walker who’s a great match for you and your dog
2. Meet & Greet
Meet either virtually or in-person with a walker to discuss the level of care needed for your dog
3. Book & Pay
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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 dog walker has to cancel, we’ll work with you to find a new walker.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Walking FAQs
Frequently asked questions about Rover
Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Winchester on Rover as of Aug 2025 was about $22 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Aug 2025, there are 9,521 dog walkers in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 84% of Winchester dog walkers respond in under an hour.
Dog walkers in Winchester have an average of 13 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Winchester.
You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:
- Start and stop times
- A map of their walk with total distance
- Pee, poo, food, and water breaks
- Cute photos and a personalized note
There are 9,521 dog walkers in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 90% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.
Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog walker 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 dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.
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