Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 80 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%.
“When our dog sitter had an emergency, Alexa saved the day! She is amazing with our 2 senior beagles, is reliable, and so sweet. I felt so comfortable leaving my dogs in such reliable hands, on short notice. It was an easy decision to have her care for my dogs again and again.”
“Noila was wonderful, she stepped in at the last minute to walk my dog who had gotten sick and needed to be checked on. She was super responsive to changes to the schedule and was prompt with the walk.”
“Rebecca was wonderful! My pup, Cleo, loved walking with her! Cleo can be anxious around new people but warmed up quickly. Rebecca even came by the house a few days earlier to meet Cleo which I thought was really great! Also, given that Cleo has only been in my life for two months and I am a first time dog mom, Rebecca gave me some helpful tips too!!”
About: Hi! I’m a dedicated pet caregiver who treats every animal like my own. Whether it’s walks, feeding, playtime, or cuddles, I make sure your pet feels safe, loved, and happy while you’re away. I’m reliable, detail-oriented, and always happy to follow your pet’s routine. I have a flexible schedule and can accommodate most requests, including last-minute needs when possible. Available weekdays and weekends, offering attentive, trustworthy, and loving care always. I treat every pet like family and care for them in a safe, calm, and loving environment. I pay close attention to routines, behavior, and comfort to ensure your pet feels happy and secure.
“Lisa treats Saturn like he is her own and that’s all that really matters to us. She always makes sure that he gets to stop by and see his friend Penny, who lives down the street. She lets him be curious on his walks and is always making sure that he has enough food and water to carry him over until we get home. Thank you Lisa.”
“Kimm & Kenn are awesome! Our pup loves walking with them, so we are return clients! They are always responsive and have great communication. They take great care of our handsome man!”
“Loved the clear, to the point communication. Blane was very sweet about making sure our pup had water, a nice walk and treats. Got a couple sweet pictures of Hank sitting nicely 😁 will definitely book when needed again in the future”
“Caitlin was great choice to walk our dog Wally. It was a bit of a last minute request and she was super responsive and flexible. We will definitely contact her again if we need a did walker!”
“Samantha is a great communicator and caretaker. Samantha is a regular dogwalker for my medium/large rescue lab/shepherd mix named Tofu, who has some level of anxiety. Samantha always updates me if there are changes in schedule or with Tofu’s behaviors during the walk. Samantha also asks questions and is attentive to Tofu’s needs, and has been building a positive consistent relationship. Thank you, Samantha for giving Tofu the exercise he needs!”
“Olha was a delight to work with and very attentive to my dog's needs and to any specific requests that I made. Luckily, she was available on short notice for both a meet and greet, and then to schedule 2 walks the next day. She obviously loves animals, has direct experience working with them, and is highly competent and responsible. I truly appreciated her responsiveness and professionalism, and my dog loved her! Looking forward to hopefully working with Olha again. She gets all the stars without hesitation!”
About: +9 Pet care experience includes hands-on tasks like feeding, walking, grooming, and administering medication, along with behavioral management and safety monitoring. Relevant experience ranges from volunteering at shelters to professional pet sitting, overnight care, and managing specialized needs for senior or anxious pets I work from home with a flexible active lifestyle. I am able to fit pet care easily into my life with how I manage everything. I have a big fenced in yard, I would treat the pet like one of my own and they would enjoy going out for hikes/walks
About: I’m a caring, dependable animal lover with a special love for cats and small dogs! I understand how important it is for pet parents to feel confident that their furry companions are safe, comfortable, and well cared for. I’m attentive, patient, and happy to follow each pet’s individual routine, including feeding, fresh water, playtime, walks, and companionship. I prioritize clear communication and providing updates so pet parents can have peace of mind while they’re away. I especially welcome friendly, small dogs and cats who enjoy gentle, attentive care! My schedule is currently flexible, which gives me availability for drop-in visits throughout the week. I’m happy to work with each pet parent to arrange times that fit their pet’s routine. I’ll carefully follow each pet parent’s instructions while caring for their pet in their home. I’ll respect their space, pay close attention to their pet’s needs, and provide updates during each visit.
“My boy was well taken care of by Heather while my partner and I were gone for a weekend. She made sure he drank water, was fed, walked, and given some cuddle time twice a day. Highly recommended. 🫂”
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.
The median cost per walk for dog walking in Winchester is $25
Dog parents share their Rover experiences - Winchester
Sanela is awesome! Our high energy labrador retriever pup had so much fun walking and playing with her. She was easy to coordinate with and sent us lots of photo and video updates. This was our first time hiring a dog walker and she made the experience great. Highly recommend Sanela!
When our dog sitter had an emergency, Alexa saved the day! She is amazing with our 2 senior beagles, is reliable, and so sweet. I felt so comfortable leaving my dogs in such reliable hands, on short notice. It was an easy decision to have her care for my dogs again and again.
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!
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 4 repeat dog walking clients
FAQs for Dog Walking - Winchester
Frequently asked questions about Rover
The average cost of Dog Walking in Winchester is $22 per walk as of November 2026. Most bookings cost between $12 and $44 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 10,611 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:
- 85% of walkers can help with special care needs
- 89% 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 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.
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