Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Winchester, Find top rated dog walking
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Kiersten was amazing with my anxious dog! She was patient with him and did a great job making him comfortable. She paid super close attention to his preferences and behaviors, which I really appreciated. She was super reliable as well.”
About: I love all animals and have fostered for the local Humane Society for the last couple of years. I am drawn to all animals regardless of type, size or breed. Sometimes the more unique the better but there’s something special about every pet. I work remotely so my schedule allows flexibility that is conducive to pet sitting. I am available 7 days a week. I can sometimes accommodate last minute bookings as well. I work remotely and love getting out for walks. I have a flexible schedule but I also know how hard it can be to entrust someone with your fur babies so I am happy to answer any questions you may have.
“Kendra was incredible! She was so easy to communicate with and provided excellent care for our two dogs. She also sent regular updates and photos. It is clear that she truly cares for animals and is very knowledgeable. We would absolutely hire her again.”
About: I have over 10 years of pet care experience including walks, overnight stays, and short visits. I also grew up with dogs and have lived with a few different cats in my adult life. I am new to the Rover app but am happy to provide references upon request. I work Monday-Friday 11-5 in Brattleboro. I can do overnights any day of the week, but just know that on these days I will be away for 6-7 hours depending on distance from your house. I love taking dogs on long walks and can do so 2-3 times a day. I am super communicative and experienced at house sitting while pet sitting. I am very respectful of people's homes and pets' routines. I will make sure to keep your house as clean - and your pet as happy - as you left them.
About: Experienced in caring for puppies, kittens, and senior pets. I provide walks, playtime, and can manage medications or special diets. I treat every pet like a cherished member of the family, ensuring they feel happy, safe, and loved while you’re away. My schedule is flexible during weekdays, which allows me to provide reliable walks, drop-ins, and pet care throughout the day. I work part time, so I’m able to accommodate many daytime and evening requests with advance notice. I make sure pets feel safe, comfortable, and cared for while keeping their normal routine consistent. I provide feeding, walks, playtime, fresh water, and lots of attention, while also keeping owners updated with pictures and messages. I’m respectful of clients’ homes and always make sure pets are happy and well cared for.
“I had a work trip and Haley was such a big help walking our pup for the week while I was away. She was very communicative, accommodating, and sent updates everyday. We would definitely ask for her help to care for our pup in the future!”
“Michael is an amazing dog walker for Theo. He is always available for us, even if it’s only a day or so warning and Theodore absolutely adores him. He sends photo updates to me which makes me so happy to see Theo when I’m gone from work! Thank you Michael!!!”
About: Hi, I am a retired dog groomer of over 35 years. Now I am a stay at home dog mom. I am pet CPR and first aid certified as well. I am up early and to bed late so I can make sure your pups can stay on their normal schedule and stay as comfortable as possible. I very strongly feel that your pet and home has your rules and find it very important to follow any instructions given to me. That means there are rules that are in place & I stick to them.
“Jeffrey is amazing! He was on time, personable and professional. He was patient with my dog and now Finn runs right away to Jeffrey. Rover is lucky to have him! As are we!”
About: Throughout my whole life there have been multiple dogs in my family. I have had my own dog before, and trained her from eight weeks old. Also, I have dog/house sat for dogs of friends and family over the years! I work in the schools so I am looking to pick up a side hustle while on summer break! I’m looking forward to a flexible schedule that incorporates my love for dogs and walking, it’s a two for one! I am very flexible and will do whatever you and your dog needs to be happy and healthy! I know what it is like to have a fur baby so I get what it’s like to do the best for them:) I am also an active person so I am able to meet the variety of needs for any dog!
About: Hi there! My name is Taylor. I absolutely love dogs and believe that most times they are better than people. I will take care of your dog(s) as if they are my own. I am available all day every day except between the hours of 3-6 pm. I love running and playing with dogs and do not mind cleaning up messes. I have two dogs of my own, a black lab and a hound mix that I absolutely adore. I love taking them for hikes and just spending as much time with them as I can. If you choose me to help take care of your dog(s), I promise you will not regret it. Thank you for taking the time to look at my profile! I work as a school teacher right now so am only available after 5 during the week and anytime during the weekends. After June 17th, I will be on summer vacation and will be available all day every day. I have a fenced in yard and a black lab that loves other dogs to play with if you'd like for me to bring them to my home to get some energy out.
About: Ive been taking care of pets since high-school, from great danes to kitties! Including but not limited to great-danes, pitbulls, hounds, labs and kitties! I am good with animals of all temperaments, from timid and not sure to excited to see anything! I love all animals and would love to help with all your pet and house needs. I am currently part time and can work around your schedule as well. I already get up to take care of my hound, pitbull and kitties. I would love to help you out as well! I love animals and have experience with the animals that also make a mess. I change litter boxes and I can even clean up after the ones who can't always hold it. I feed, and give fresh water. I walk dogs and also have experience with pulling. I can also just let them out if trained to do so and hangout with them as needed!
About: I’ve been around animals since I was 8. I’ve fostered animals, and helped walk, feed, bathe, supply medicine (supplements and pills) to them for friends, family, etc for a little over 8 years now. I’m very experienced with younger dogs and can provide extensive walks / playtime for entertainment and engagement. I also love working with senior dogs as well, and can help provide a calm, stress free environment for them while their owner is away. I’m currently working part-time from home and have a very flexible schedule! I can do drop in visits, overnight stays, and even long weekends / weeks for vacations and getaways! Early mornings and late nights are no problem for me as well. I don’t mind cleaning up messes or puddles, and I can travel very flexibly if needed! I am OK helping with crate training, and providing a positive environment for any pup to grow in while their family is away! I have a fur baby of my own who is almost 4 years old, and absolutely adores other dogs! He is neutered, house trained, and very relaxed. He has been a very good role model for our youngest puppy in the house.
About: I worked in an exotic vet hospital for 7 years which is also a wildlife rehab facility. Prior to that I have raised and cared for animals of all species of my own my whole life. Whether fury, feather, scales, or more I love just about every living being & critter. I will care for your pets like they were my own. *Making a note that poisonous/venomous or illegal animals are not acceptable or allowed. I have experience with reptiles like geckos, bearded dragons like my own, iguanas, turtles, birds of all shapes, color, and sizes, some farm animals, ferrets, guinea pigs, hamsters, rabbits, and things of the like. Animals that are venomous or harmful are excluded.* I care for and hang out with my fur babies, but there's plenty of room and time for more friendly faces. I work hard so my pets can have a good life. I frequently walk my dogs and can take yours around the neighborhood as well, lots of dog toys, pats and belly rubs, and can crate your pup if needed. I'm also willing to help with some trainings and house breaking if requested.
The median cost per walk for dog walking in Winchester is $25
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- 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.
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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Meet local walkers who will treat your dogs like family
1. Search
Browse profiles of walkers near you who offer dog walking
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Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for dog walking - Winchester
Select a filter and find qualifying sitters offering dog walking.Sitters in Winchester average 3 repeat dog walking clients
FAQs for Dog Walking - Winchester
Frequently asked questions about Rover
As of September 2026, there are 423 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:
- 89% of walkers can help with special care needs
- 97% can help with giving oral medications or injections
- 94% 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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