Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 73 pet parents in Winchester have booked dog walking
Winchester, Find top rated dog walking
Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“James was extremely communicative and friendly. He followed all instructions and reached out when he needed questions answered. Will definitely ask James for help in the future!”
“If you are looking for someone who will treat your dog like family, then book Felicia! She is amazing! She took the time to meet our dog prior to walking him, and made sure she understood everything about him prior to walking him. She is also very communicative and takes a lot of pictures during their walks. I’m so glad we met her, and now our dog has a new friend too!”
“Alexa is fantastic! We hired her for daily walks, and she shows up on time, walks further than she has to, and provides great feedback through the app. Our dog loves her and she’s great with communication. Would definitely recommend!”
“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!”
“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”
About: Dogs are more than just pets…they’re family and vital companions in our daily lives. With over a decade of hands-on experience caring for pets of all shapes and sizes (from geckos to Great Danes), I bring a calm, attentive, and knowledgeable approach to dog sitting and walking. I am currently in a mentorship and shadow program intensive to also become a dog trainer, so your dog will also get to practice some skills with me! My journey with dogs began early with family pets and expanded into dedicated pet sitting for neighbors and friends. As a lifelong learner, I’ve spent years studying dog behavior, body language, and communication styles through training my own dog. I have experience working with reactive dogs, maintaining strict routines, and using consistent, structure to make every pup feel safe and secure. I also regularly assist a close friend who is a professional dog trainer, which has given me great insight into handling diverse personalities, energy levels, and care needs. Outside of pet care, I work as a mental health therapist. My professional background deeply informs how I interact with animals. I understand the reciprocal bond between humans and their dogs, and I treat every animal in my care with the utmost empathy, patience, and respect. What to Expect Attentive & Safety First Care: Whether keeping up with medication, supporting structured routines, or managing triggers on walks, your dog’s safety and comfort are my top priorities. Active Adventures: I love helping dogs explore! If your pup enjoys an active lifestyle, I’m happy to take them along for hikes, trail walks, or gentle runs tailored to their fitness level. Tailored Communication: You’ll receive clear, regular updates and photos so you can have complete peace of mind while you’re away. Whether your dog needs a chill check-in, a structured neighborhood stroll, or a outdoor trail adventure, I’ll provide the exact same devotion, care, and attention I give to my own dog. I look forward to meeting you and your pup! I currently work from home as a mental health therapist. I am able to make my schedule and work around your pet’s needs as needed! There will always be time for potty and play breaks. I have a large yard, as well as my dog who is crate trained. If staying at your home, I would love to be clear on your pet’s schedule so they can have consistency. I also love having adventure buddies, so if your dog likes to be out in nature for trail walks or swims, I’m your gal!
“Liz is an amazing caregiver for our little pup! She gives attention to his puppy experience and communicates with me about the details. She really cares and is so very capable with pups!”
“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.”
“Ugur provides top-notch service walking our dog. He is kind and friendly. We hired him to walk our 7-month old puppy and she loves him. Although we hired him to walk our dog, when he came for a meet and greet, our cat warmed up to him immediately and let her pet him, which she normally doesn't do for most people. We highly recommend his services!”
“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.”
About: I know first hand how much love there is between a dog and their owner. For that reason, I believe trust, transparency, and fun are the pillars of my dog walking service. When you entrust me to care for your pet, I will make sure they are always safe, hydrated, and having fun! I also always send updates after walks letting clients know how the walk went and that dogs are home safe. As a dog owner, I have had family dogs ranging from a 6 lbs Yorkie to a 65 lbs Lab. Outside of my own pets, I have experience cat- and dog-sitting for friends and family and am excited to be able to take on more dog walking clients. I am comfortable walking dogs of many breeds, sizes and ages. I can't wait to meet your furriest family members! I am a graduate student, so I often have a flexible schedule to work around your needs. I am available for early morning and evening walks every day of the week and midday walks every day Wednesday-Sunday. Safety is my top priority for your pet, your home, and myself. This is why before working with your pet, I will request a meet-up with you to better understand your pet. In this meeting we can discuss if your pet has any aggression or fear around other dogs, escape-artist tendencies, or special needs so that walks can be as safe and secure as possible.
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.
“So sad to be moving as Cheryl was the best dog walker. She was always available with my chaotic schedule. My dog loved her almost as much as he loved her homemade treats. Highly recommend Cheryl.”
About: I have been around animals since I was born. Something I learned from my father was that our animals weren't just some objects and that they were part of the family. I've had cats, dogs, and fish. I am also a quick learner and am able to adapt to whatever routine is needed to care for your animal the best. I am doing my masters at tufts university, but most of the weekdays I have big gaps in the middle of the day. During this time I can care for animals in whatever way needed. I have 6 cats and 1 dog in my family home where I currently commute from. I walk the dog usually once a day, i clean cat litter once a day, and feed all animals regularly.
“Kimm is AMAZING! She’s very communicative and our 3 dogs love her. She’s intentional about making sure they get a good walk and giving a detailed report card on each pup!”
“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.”
“Lauren has been so thoughtful and kind with our pup Keira! Keira had recently been bit when Lauren started with her, which meant she had some reactive behavior around other dogs. Lauren kept us updated every walk on how she did, and was open to using some of the training methods we used with Keira to help on walks. I would highly recommend Lauren for walks with your dog!”
About: Hi all! I have cared for pets on the side for the past few years. I am an animal lover. I have experience with sitting, walking, visits, and med administration. I am a Registered Nurse and a warm, loving person which definitely comes out in my work animals. I am super responsible, I have a flexible schedule and I am often available for last minute requests. I have experience with nervous rescue dogs, senior dogs, and very large dogs who pull on the leash. I live in East Boston but commute to Winchester often so I am available anywhere around those areas. I am super interested in getting to know you and your pets! Thank you so much and please feel free to ask my any questions that you may have.
The median cost per walk for dog walking in Winchester is $25
Dog parents share their Rover experiences - Winchester
We’ve met Sanela a few times at our dog park and knew she would be a great walker. She spends lots of quality time with both our mini aussies in the dog park and we really appreciate her! Can’t go wrong having her walk your furry friend(s), she loves all animals!
Shawn walked our Goldendoodles every day while we were away and a family member was housesitting. Excellent communication, reliable, and trustworthy, Shawn made it possible for us to feel comfortable that our boys were in good hands while we traveled. Would definitely work with Shawn again! Highly recommended!
Jade went above and beyond with our dog, Brody. He does require a bit of extra care and Jade took it on without skipping a beat, making us feel that it was no issue at all and additionally watering our plants on top of everything. She was able to alleviate so much stress from my week by treating Brody with such attentiveness, being punctual and being an absolutely exceptional communicator. I cannot wait to work with her again.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local walkers who will treat your dogs like family
1. Search
Browse profiles of walkers near you who offer dog walking
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog walking - Winchester
Select a filter and find qualifying sitters offering dog walking.Sitters in Winchester average 4 repeat dog walking clients
FAQs for Dog Walking - Winchester
Frequently asked questions about Rover
The average cost for Dog Walking in Winchester on Rover is $22.2 per walk (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .
As of September 2026, there are 10,604 sitters on Rover offering Dog Walking across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.
Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Winchester. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winchester.
Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
Yes, you can find walkers who have experience with handling special pet needs in Winchester. On Rover:
- 90% of walkers can help with special care needs
- 94% can help with giving oral medications or injections
- 97% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.
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