Dog Walking Winchester Estates
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 5 pet parents in Winchester Estates have booked dog walking
Winchester Estates, 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: As a mom and lifelong animal lover, I understand how important trust is when someone cares for your pet. I offer dependable, attentive care in a calm home setting. I’m patient, nurturing, and detail-oriented — making sure your dog feels loved, exercised, and safe at all times. My open schedule allows for consistent supervision and care. I’m flexible with my time and available most days and weekends which allows attentive care :) I care for pets in my home, offering a secure and relaxed setting while you’re away. They will be comfortable safe and always loved :)
About: Hello everyone, I’m back and accepting new clients once again! I am Reliable and experienced sitter/walker ensuring your canine companion gets the exercise and attention they need. Tailoring visits to suit each dog's energy level and personality for a joyful experience. Pet Sitter: Trustworthy care for your furry friends while you're away. Offering personalized attention, exercise, and companionship to keep your pets happy and healthy. Experienced in caring for special needs dogs! I work part time and I’m in school but I have some free time and would love to fill it by providing care for your pet 😄 I generally accept last minute bookings unless I genuinely will not be able to provide proper care. I will pick up/drop off your pet no matter what side of the bridge you live on-don’t hesitate to ask! I genuinely love dogs and will go out of my way to make sure their needs are met. I currently live in a house in Grasonville with lots of property and grass. It is on the water with a lot of trails for some nice dog walks! I tailor each visit to suit the individual dog’s needs.
About: I’ve taken care of dogs my entire life whether that is my own dogs at home or helping out a neighbor or friend! I would love to help your dog as well I’m currently a student at Salisbury university but I am commuting so I only have classes on Tuesday and Thursdays. I am available almost any other time besides then! I will be there for whatever your pet needs may be! I love taking care of dogs of all sizes and know what it takes to make sure they will be ok while you are gone
About: I have hands-on experience caring for my own dogs, Koda and Eddie. Koda is a Cane Corso puppy, which has helped me learn the importance of patience, consistency, positive reinforcement, and proper exercise. I make sure my pups receive plenty of love, attention, playtime, and daily care while keeping their safety and comfort a priority. I understand that every dog has a unique personality and needs, and I would treat every pet in my care like family! 🐶❤️ Pet care is something I enjoy and make time for in my daily schedule. I strive to be flexible, dependable, and attentive to each pet’s needs, ensuring they receive plenty of exercise, attention, and care. I communicate with pet parents to coordinate schedules and make sure every pup gets the time, love, and attention they deserve! 🐾 I prioritize safety, patience, and trust when caring for every pet. I make sure each animal feels comfortable, loved, and secure while following the owner’s instructions and respecting each pet’s unique needs. I believe in keeping open communication with pet parents, providing regular updates, and creating a safe, welcoming environment where both pets and their owners can feel confident and at ease. My goal is to treat every pet like family! 🐾❤️
About: Hi, I’m Hannah — a responsible, caring pet sitter who treats your home and pets like my own. I know how difficult it can be to leave your furry family member behind, so I’m here to give you peace of mind with loving, attentive in-home care. Whether your dog needs belly rubs, playtime, medications, or a quiet companion on the couch, I adapt to their unique needs and stick to their usual schedule. I’ll also keep your home tidy and safe so you can return to everything just how you left it (or better!). ~Staying overnight at your home ~Feeding, walks, and potty breaks on your schedule ~Playtime, snuggles, and companionship ~Administering medication (if needed) ~Daily updates with photos and notes ~Light home care (mail, plants, trash, etc.) ~Respectful, clean, and professional behavior in your space Hi! I’m Hannah, a very energetic stay-at-home mom. I can’t wait to welcome your pets into my life! I'm home full-time this summer, so your dogs or cats will get constant attention, affection, and supervision while you’re away. I'm a huge animal lover — patient, kind, and great at following routines. Whether your pet needs playtime, snuggles, walks, or quiet companionship, I'll provide a safe, loving environment that feels like home. Our animals are happiest in their environment with their familiar smells, toys, and routines. I help minimize stress and keep them comfortable while you enjoy your time away, worry-free.
About: I’ve taken care of my own dogs since I was 8. I had a medium sized low energy dog and now I have a high energy bigger dog so I have a good range of care. I’ve always been the one neighbors have reached out to to take care of their dogs Currently I am unemployed so I am pretty openly available! It really just depends on your dogs needs and how I can best provide for them! I am really good with handling dogs and getting them to listen. I’m super athletic so I’ll love taking your dogs on walks and playing! Super openly available for all there needs.
About: I absolutely love animals. I currently have a black lab and I love to just spend time cuddling with her, or going for long walks. If possible, I try to bring her along (assuming they get along at the meet and greet). I’ve noticed that dogs can wear each other out a lot faster than I can, and probably have more fun doing it too. Maddie gets along with everyone and just loves to meet someone new. For your dog, I will treat him/her as my own. I will play with them and take them for walks. I have no problems cleaning up messes, sometimes accidents happen. Let me love and take care of your pet so you don't have to worry about them during the day. Why I love dog sitting I've always been an animal lover. I've had dogs all my life and had two of my own. They truly are the best things that ever happened to me. I’m very active, so I would spend as much time outside as possible with your fur baby. My experience administering medication: I am fine with administering medication, but would like to have the owner show me the correct way of doing it before I start.
About: I am currently employed as a kennel attendant and a veterinary assistant where I have gained experience in dog handling, feeding, medicating, and more. I have experience with dogs of all sizes, breeds, and temperaments. I am currently working part time at 2 jobs attending college. My schedule changes weekly but I always have extra time to watch your pups! I am located on Kent Island and I am not able to provide services over the Bay Bridge. I am not currently offering boarding in my home however I would be more than happy to watch your animals in your house.
About: As a dedicated dog walker and in-home pet sitter with over two years of experience, I know how important it is to find someone you can truly trust with your pet. I care for every dog (and cat!) as if they were my own — with patience, love, and attention to their unique needs and routines. What You Can Expect: ✅ Safe, fun, and tailored walks ✅ Home visits that follow your pet’s schedule ✅ Clean water, food, meds (if needed), and lots of affection ✅ Daily photo updates and messages so you never have to wonder how things are going ✅ Respect for your home and your pet’s space I’m trained in basic pet first aid and always check collars, leashes, and gates before heading out. Whether it’s a quiet walk or an energy-burning play session, your pet's safety and happiness are always my top priority. Let’s schedule a meet-and-greet! I’d love to learn more about your pet and how I can help make your time away stress-free for both of you. 🐶🐾 Pet care fits naturally into my daily routine because of how flexible and rewarding it is. Since I set my own schedule, I can book pet care clients around my part-time job shifts and study blocks, which helps me stay balanced and productive. Walking dogs gives me a much-needed mental reset from screen time and studying, and it keeps me active throughout the day. It’s also a great way to supplement my income without taking on another traditional job. Most of all, spending time with animals brings me a lot of joy and motivation — it breaks up long study days and reminds me why I love what I do Whether you’re at work or away for a few days, I provide reliable, in-home care that keeps your pets safe, happy, and stress-free in their familiar environment. From daily walks to feeding, playtime, and medication routines, I tailor every visit to your pet’s unique needs. 🔐 Safety & Professionalism Equipped for pet first aid always carrying a kit Detailed home-entry and security protocols Leash and harness checks before every walk Weather-conscious and always alert to potential hazards Respectful of your home, your pets, and your time 📸 Peace of Mind After each visit, you’ll receive a photo and short update so you know how your furry friend is doing — because trust is built on communication
About: I have a one year golden retriever who I raised on my own since he was 8 weeks. I’ve also have experience pet sitting, walking family and friends animals throughout the years I’m currently working full-time on the weekdays and attending AACC gnursing school starting in August . However I have open availability to watch your fur babies all through out the weekend! I have a friendly golden retriever boy to keep your fur babies occupied. I’ll be home majority of the day to keep them comfortable and safe.
About: Hi, I'm Michael, a dependable pet lover in the Pasadena, MD area. I offer dog walking and drop-in visits, and every visit includes fresh water, feeding on your schedule, potty breaks, playtime, and a quick photo update so you know how your pet is doing. I have been a pet owner ever since 1995 and am comfortable with all sizes and types. I'm careful and patient and treat every pet like family. I'm available during the week and most hours and I live close by, so I can be flexible for last-minute visits. I have reliable transportation and I always show up on time. I'd love to meet you and your pet before the first booking so we can go over routines, quirks, and anything special they need. Thanks I am currently working part time doing deliveries and pet care. I have a full fenced back yard and a basement if crates are needed but prefer to keep animals out of crates. I have a fenced in yard and my house is sectioned off top and bottom, as well as rooms that can be used for the animals as needed.
About: Damola has over a decade of experience caring for pets and is currently available for walks, check-ins and house sitting. She focuses on creating a safe, nurturing environment tailored to each pet's unique needs and preferences, incorporating stimulating activities, personalized care, and open communication with owners to ensure a positive experience for both pets and their human. I attend grad school in the evening from 6-9:30 PM Monday-Thursday, but will be done with classes in early May. On the weekends I am completely free. I can take your pet out on walks multiple times a day. I live with my 2 year old Beagle mix who is very active and friendly with other pets.
About: Hi, I've been around pets for the last 15ish years with that I've learned that not all dogs are the same and will react the same way towards everyone. I have worked with dogs who were previously in shelters, nervous dogs, fearful dogs, and anxious dogs. I have experience dog sitting small and big dogs. I have potty trained my own dogs and have helped friends potty train as well. I'm comfortable with bathing, brushing, feeding, walking, and interacting with dogs. I have worked with special needs dogs and am comfortable changing their diapers, applying creams and ointments, and applying wraps or bandages if needed. I'm comfortable feeding, cleaning litter boxes, and brushing cats. I've also taken care of small reptiles like bearded dragons and geckos, as well as birds like cockatiels and parakeets. I just moved to the area and have flexible availability. I am available for drop ins and walks throughout the day. No time is too early or too late. I'm open to last minute drop ins or walks as long as it is communicated. I'm great at sticking to your pets eating schedule as well as establishing routines if needed. I'm able to clean up after your pet, feed them, interact with them, and stimulate their brain as well.
About: I’ve taken care of various different species of dogs and cats within my neighborhood and area since I was 10! I’ve always been an animal lover so many of my neighbors counted on me to take care of their fur babies! Within this years worth experience, I have learned to work with different species of dogs & cats! I am able to work with cats and dogs of different personalities, traits, needs, etc! Neighbors have relied and trusted me to feed, walk, bathe, spend time and show loving to their beloved pets! I’m currently a part time collage student but I still have a lot of time to play, care for and show so much love to your fur babies! I am available Monday, Wednesday, Thursdays, Friday, and Sunday after 12:30 pm!🧡 In my clients home, I always ensure the pets safety! I make sure to check surrounding and keep things out of reach that could harm the animal! I always make sure to introduce myself slowly as I am in their home and allow them to get comfortable with me at their own pace. I always ensure to go through and memorize their routines and feeding schedules. I always respect the home owners home as well and make sure it stays clean!
“Alexandra was amazing to work with! Had a last minute trip and she was prompt and very easy to work with! Pups loved her and we will definitely be using her services indefinitely??”
About: Taken care of almost all dog types since the age of 12. My family & friends rely on me to take care of their babies I am currently unemployed so everything literally works perfectly for my schedule and for any future pet sitting accommodations. I have more than enough time with assistance hourly,daily or weekly I can easily have the crate for your dog if needed also no exterior pets for the most part your dog will be well aware of comfort & all the support s/he needs
The median cost per walk for dog walking in Winchester Estates is $20
Dog parents share their Rover experiences - Winchester Estates
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?
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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 Estates
Select a filter and find qualifying sitters offering dog walking.Sitters in Winchester Estates average 3 repeat dog walking clients
FAQs for Dog Walking - Winchester Estates
Frequently asked questions about Rover
The average cost of Dog Walking in Winchester Estates is $16 per walk as of October 2026. Most bookings cost between $6 and $16 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 October 2026, there are 2,236 sitters on Rover offering Dog Walking across Winchester Estates. 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 Estates. 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 , 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 Estates 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 , 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 .
Yes, you can find walkers who have experience with handling special pet needs in Winchester Estates. On Rover:
- 88% of walkers can help with special care needs
- 93% 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 .
walkers on Rover set their own , 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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