Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 1 pet parents in Winchester have booked dog walking
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.
About: I have a life long passion for animals and have had animals my entire life! Right now I have 3 dogs and 1 cat. I've had cats and dogs, and although I haven't had a reptile, bird or small animal, I attended an agricultural high school at which I helped care for these animals. At the school, I volunteered at an animal daycare for teachers and was in charge of our "woof wash" where be bathed and clipped animals nails. I am always happy to walk and play or just sit on the couch and hang out. I worked in an animal shelter caring for both dogs and cats for 4 years in high school. I don't currently volunteer at a shelter but in the past I have volunteered at Little Guild of St Francis, and Home at Last in Philadelphia. Even in my spare time I love to learn more about dogs and spend time with pups that need it the most!
About: I’ve cared for many different animals throughout my life, including mammals, birds, reptiles/amphibians, exotics, farm animals, and wildlife. I’ve cared for pets of friends and family. I have experience with overnight sitting in the pet’s home. I also have experience caring for senior and special needs animals. I spent 6 months as a volunteer at a vet clinic assisting with exams and surgical procedures, and I am currently exploring career paths in animal sciences and wildlife rehabilitation. I have lots of availability to care for your fur babies! I work part-time as a waitress while exploring different careers in the field of animal behavior and sciences. I have the flexibility to accommodate to your schedule and needs. I can be available on most weekends and holidays. I also accept same-day bookings. I prefer to care for animals in their own home where they feel most comfortable. As well as walking in areas they are familiar with. I always make sure to maintain pet safety in the home such as keeping doors/windows/gates shut and keeping hazardous items and toxic plants out of reach or locked away.
“Ashley is a delight. She was very communicative and caring about our elderly dog with special needs. We only needed her to come and take him for a walk, but he is blind and deaf and also wears a diaper. She let us know when she got to our house and sent pictures afterwards. We felt very comfortable with her and will definitely be using her again.”
About: I provide loving, attentive pet care, ensuring pets feel safe, comfortable, and happy while maintaining routines, exercise, feeding schedules, individualized attention, and clear owner communication. (Bilingual) Habló español Pet care fits into my routine part-time and per diem, allowing me to dedicate quality time, flexibility, and focused attention to each pet without feeling rushed. I follow each pet’s routine closely, including feeding, walks, playtime, and rest. I keep environments clean, safe, calm, and provide regular updates to owners for peace of mind.
“Priscilla is awesome. Our dog is very nervous with people and this is the fastest she has gotten comfortable with someone new. She takes great care of our dog and our dog always comes back happy after walks!”
About: I’ve been an animal lover for as long as I can remember! I grew up with Labs, so I’m very familiar with big personalities, lots of energy, long walks, playtime, and plenty of slobbery love. 🐾 I also adopted a cat, which taught me that sometimes the best way to win a pet over is to let them come to you (and maybe offer a few treats!). Although my own pets have since passed, they gave me years of experience, amazing memories, and a genuine love for caring for animals. I’m patient, playful, attentive, and always focused on making pets feel safe and comfortable. Whether your pet wants an adventure outside, a game of fetch, or just some extra love and company, I’m happy to be their new buddy while you’re away! ❤️ I currently own my own business and make my own hours and work from home, so I can easily make my own schedule fit around any pet care! I'm lucky to have an open, comfortable and clean home where I can walk animals on the many acres I live on. I can also crate animals if that's how they are trained. When in other people's homes, I'm incredibly conscious of being considerate, following directions to respect their space, and understanding how the animal uses and loves the space.
About: Hi all! I’ve been pet-sitting since very young (age 10), having experience with various dog breeds and sizes as well as cats. Feel free to reach out so we can connect! I currently work per diem, so I have plenty of free time to care for little ones. I tend to have open availability, even for last minute requests! I am very open and able to follow any requests concerning your little ones. I understand that every pet is different when it comes to their needs, so I am very accommodating and willing to learn how to best care for your baby!
About: Dogs have and will always be a huge part of my life. We got our first family dog when I was just 3 years old and the rest is history. My husband Jack is extremely passionate about animals as well and is my partner in all of this so you get two dog sitters for the price of one. Between the two of us your pet will get so much love, cuddles & exercise. We guarantee a level of attention and care that I feel confident your pet won’t get anywhere else; between this and Rover taking it’s fee our prices might be on the high side but they reflect our level of personalized and professional level of care. I also just want to add that our love for dogs extends to all animals so cats etc are all welcome to come hang with us :) Important Note: if you are reaching out for house sitting my husband and I only take those if we both are allowed to stay the night. We prefer to do this for safety as well as enabling the best care possible for your pet. Your pets will be my top priority & my main focus when they stay with us! I feel pretty confident that they will get more quality time, attention & lovin with me then any other pet sitter! I have a smoke free home and do not have any dogs currently living at my house so your pets will be my only focus! Also a child free home!
About: I’ve always taken care of pets and volunteered at local shelters. Your doggies will have the option of treats, dog walks, dog park trips, bark toys, and the option to socialize with other dogs if that is an option! What’s different with me is every dog that stays here with me and comes home with a brand new BARK BOX toy if the parent allows ! I’m currently a stay at home dad so this works perfectly with my schedule! With my wife working full time, this makes a household that much more at home! All of my dogs are trained and with the huge yard in our back yard it provides the perfect area for exercise and potty time! We also have a dog park right down the street!
About: Hi! Im 24 and I live on Amston Lake and I love to walk dogs! I have a lot of free time in the mornings before work and on my days off. I am open to walking big and small dogs! Also open to walking more than one dog at a time! I have a 8 year old Shihpoo that is very dog friendly! I also have two indoor cats! Let me know if he can join on the walk with your dog! I would prefer walking dogs around the lake, but I am open to going to new neighborhoods, trails, or dog parks! I am currently working full time, I work a 5 on 2 off, 5 on 3 off schedule (evening hours) so my days off change every week. I have a lot of free time in the mornings before work and on my days off. On my days off I am available all hours! I can provide walks around the lake, nearby neighborhoods, dog parks,and hiking trails. I am open to feeding pets, letting them out to use the potty, and play time!
The median cost per walk for dog walking in Winchester is $22
Dog parents share their Rover experiences - Winchester
Stacey is so incredible!!! She is communicative, flexible, and so kind. She took amazing care of my girl and went above and beyond to be helpful. A bear knocked over our recycling bin and she picked it all up, she brought a package in, and most importantly she made our dog so so happy!! We will call Stacey any time we need a little help with Blue going forward!
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.
How to book dog walking
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 3 repeat dog walking clients
FAQs for Dog Walking - Winchester
Frequently asked questions about Rover
As of November 2026, there are 1,531 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 Winchester. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.
The route map lets you review where your dog was walked in Winchester after the booking. It is not live GPS tracking.
Have specific details you would like included? Message your dog walker in the app before the 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
- 91% can help with giving oral medications or injections
- 96% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
walkers on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.
Connect anywhere with the Rover app
