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.
“Haley is absolutely wonderful! She is great at communicating things ahead of time and is very flexible if there’s a last minute change in the weekly schedule. My dog absolutely loves when it’s a “Haley walk day”. Absolutely recommend her!”
About: Growing up in Vermont on a farm, I have been exposed to animals my entire life. I have been taking care of family and friends dogs, horses, cats, guinea pigs, camels (yes, camels) since I was allowed to leave the driveway on my bike as a child. Since leaving high school I took on a professional equestrian career with Wichita riding academy working with rehabilitating abused/ off the track race horses. I have just recently moved to Denver with a fenced in yard and lots of space. I have a dog of my own that is my entire pride and joy who loves spending time with other dogs. Having a fenced in yard, it’s very helpful and handy to those pups with bladder issues to go in and out of the house as needed. My home was completely childproof when I moved in and it’s so far worked for dogs as well. Huge open field located next to the house available for dogs who like to run 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.
“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 used to babysit for my friends, family membersand & neighbors. As well as I've had many pets of my own; cats, dogs guinea pigs, hamsters, you name it. I'm very good at handling bigger dogs. I'm very flexible when it comes to time and will work around your schedule. I'm currently home from college for spring break and my time is very open for both weekends and weekdays. My working hours start at 7am and go till 11pm. (But I can fluctuate with your schedule) I have a fenced backyard. And one very friendly small/medium dog, he's a little shy, but he gets along with everyone. I believe that our pet should be treated like family members. Walks, treats, attention and lots of love.
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: I’ve always loved animals and have spent many years helping friends and family take care of their pets. It’s something that brings me a lot of joy. Over the years, I’ve looked after all kinds of pets — from energetic pit bulls and bulldogs to small dogs like Shih Tzus and even cats. Sometimes I’ve stayed in people’s homes for a week or two, and other times I’ve just stopped by for walks or check-ins. I’ve also welcomed pets into my own home when friends needed someone they could trust. I have a calm, friendly personality and get along well with animals, even if we’re meeting for the first time. I’m always careful to notice when a pet might be nervous or needs some space, and I do my best to make sure they feel safe, happy, and cared for. My schedule is very flexible since I work a per diem job and can choose when to take shifts. This gives me plenty of time for pet sitting, walks, or overnight stays. I’m usually available on short notice, too. The only thing I plan ahead for is care for my own cat while I’m away, but that’s easy for me to arrange — so it won’t affect my availability or reliability. When I’m caring for pets in their own home, I do my best to keep their routine as normal and comfortable as possible — feeding, walks, playtime, and cuddles just the way they’re used to. I make sure they feel safe and cared for while their family is away. If a pet stays in my home, I treat them like one of my own. I create a calm, cozy environment with plenty of love, attention, and playtime. I also make sure to follow any specific instructions from the owner so each pet’s needs are met. I’m gentle, patient, and understanding of different personalities — whether a pet is shy and needs space or energetic and ready to play.
About: I have taken care of cats, dogs, Small animals like mice, guinea pigs, fish, turtles. All way to farm animals like sheep, goats and even horses. Due to growing up in small town farming community. Currently I am supervising and helping my teenage daughter care for multiple miniature and full size horses in Leverett MA. I also have two wonderfully spoiled cats and a dog at home. Have some openings in evening and most weekends as at this time I do have a full time 9-5 job. Looking to see where this goes. I do not have fenced in yard but I keep my current dog on tie out or 50ft lead. Very quiet not normally traveled area around house with big yard to play. At clients home depends on environment there. Would prefer no off leash unless securely fenced area.
About: Hi! I'm Nicole. I'm a software developer & animal lover. I've been around dogs since I was little and have always wanted to adopt one. Caring for dogs with busy owners is a great compromise! Dog owners will love that I will treat their furry pal as if they were mine. They will also love that I have private outdoor space for playtime, anytime, and am right next to central park so there's alot of ground for your furry friend to explore! I truely care about your pets well being so I am consistent with feeding time and will always make sure your furry friend is comfortable, whether its brushing her or refilling her water bowl. I am available Wednesdays and the Weekends for pet sitting, walking, and house sitting. If you are going away for a weekend and need someone to house & pet sit, I'm your girl!
“Excellent service and great relationship with Chessie. Kendra did everything I requested in walking Chessie and giving her meals. This was the second time I have engaged her and would definitely engage her again if the need arises.”
About: I've had animals since I was a child. I have helped neighbors, friends, and family members care for their furkids. Walking, feeding, caring for them is the least I can do. I provide them with love as if they are my own. I'm currently working at a job that allows me to come and go as I please with plenty of flexibility. I can help at anytime of any day! I have a fenced yard for my 3 Siberian Huskies and my golden retriever. I also have a Cat, 2 Green Cheek Conures, a Chinchilla, and a Sugar Glider. One of my Dogs is Diabetic so I have plenty of experience with administering oral medications and injections.
About: I have been around all different kinds of animals since I was a child and have always had a special love for them. All pets deserve unconditional love and kindness, and I am here to help with that! I am working full time from home and am able to adjust my lunch break for pets that need a walk or need someone to check in on them! I am available after 5 on weekdays and am completely free on weekends. Each pet has their own personality, so care will need to be adjusted to meet the needs of each pet. I have plenty experience in high energy dogs as well as very lazy dogs. Some need pets, cuddles, and a walk whereas some will need lots of running around to get their energy out! I am capable of both and will honor what you feel is best for your fur baby.
About: hi! I am new to pet care, I have taken care of children my whole life! I am Looking forward to gaining experience and knowledge! I am a college student first so I tend to only sit during the weekends, or after class on weekdays if necessary. I’m slightly flexible though! Feel free to reach out :) In your home, I do my best to keep everything just the way your pet (and you!) like it. I follow your routines, stick to their feeding and potty schedules, and give lots of love and attention so they feel totally at ease while you’re away. I’m tidy, respectful, and treat your space like it’s my own. In my home, your pet will be treated like royalty—with a comfy place to nap, toys to play with, and plenty of one-on-one attention. I only take in pets I know I can fully care for, so your furry friend always gets the time and love they deserve. Whether I’m visiting them or hosting them, I make sure every pet feels safe, special, and very, very loved.
About: I have had dogs & cats in my life since childhood. A parakeet too! I know how close we become to our pets & how important good care is. I have 2 dogs of my own & have devoted myself to giving them the best life possible. I am newly retired so have lots of time to take care of your beloved pets. I love walking & playing with dogs in all kinds of weather. I will take great care of your pets at your home or while you visit Boothbay Harbor for a few hours or for a day! I will follow your instructions, making sure they are happy & safe. We will always have fun! I am retired and, thus, have quite a bit of time to walk & spend time with your beloved pets!! It’s more than a “job” for me. It’s a labor of love as well. I have a fenced in yard that our dogs use and would prefer walking and caring for your dogs at your home where they are more familiar with the surroundings.
About: I’ve taken care of a tons of breeds of pups. I have taken care of dogs from puppies to older dogs as old as 17 years old. I have been taking care of dogs ever since I was little. I am able to walk, feed, play fetch, provide overnight care, and make sure your home is safe and sound while you need assistance. I look forward to meeting your pups! I’m able to provide care for your pups as I have a flexible schedule and am able to work around when you need assistance with your pups! I will care for your pets and give them attention constantly. I wake up early and feed them, and make sure they are all set for the day. I will snuggle with them and make sure they are safe :)
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.
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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How Rover works
1. Search
Browse profiles of sitters near you who offer dog walking
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests near you
Select a filter and find qualifying Winchester sitters!Sitters in Winchester average 3 repeat dog walking clients
FAQs for Dog Walking - Winchester
Frequently asked questions about Rover
As of July 2026, there are 477 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:
- 87% of walkers can help with special care needs
- 97% can help with giving oral medications or injections
- 95% 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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