Dog Walking Winston Terrace
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 64 pet parents in Winston Terrace have booked dog walking
Winston Terrace, 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.
“Excellent experience! Tess was punctual, followed all instructions, and handled my high-energy pup with confidence and care. Tuco was happy, well-exercised, and calm when I got home—something that doesn’t happen often. Highly recommend and will definitely book again.”
“My little girl usually takes at least a brief time before she warms up to a stranger like she did to Honey. It was just about instantaneous. She was ready to go for her walk as soon as she was at the door. I think she was somewhat disappointed when it had to end. I will definitely use again.”
“Excellent service and our dog is in great care with Hadley! We appreciate her care, responsiveness and pictures and updates and would highly recommend her to help with your pets! :)”
“Nice gentle with my girl. Willing to try whatever thought would motivate, but usually based on what I suggested. Appears to be cautious and not wanting to hurt dog. Definately likes animals. Much interactive with my dog after we all called it a day. Client was being very recalcitrant. Perhaps do some bonding before attempting walk next te”
“Victoria is amazing! She is extremely communicative and reliable in her services. I have a nervous pet and she went above and beyond to ensure that my dog and I were at ease. She was also able to help me in short notice. She is fantastic and I plan to use her again in the future :)”
About: My beloved Summer (now deceased) was an absolute monster when she was a puppy, so I can handle it all. When she was a senior, I had no problem picking her up (60 lbs) for car rides and for bedtime (she slept with me), and took care of her when her stitches popped. It takes a lot to faze me. In high school and college, I was first aid certified and still keep a first aid kit on me at all times, so should something happen, I can get your sweet dog wrapped up if need be. My favorite activity for getting dogs' energy out is taking them to a fenced in soccer field and kicking a ball for them to run after. I currently have a 6 (ish) year old rescue named Charlotte, whom I’ve had to train as an adult dog. She’s the complete opposite of Summer: very vocal and has no interest in balls but adores sticks. Every morning, afternoon, and evening. Walks, meal times, and play time for your dog (or dogs) and my dog as well. Caring for a dog is priority #1. Each morning, I walk Charlotte before hitting the gym and again in the evening. I’m currently in-between jobs, so I have full availability for the next few weeks. After that, I will likely be working remotely and will be flexible. It varies by the needs of the pet and his/her family. Walks, playing in the yard, etc. are common. If your pet has a certain routine, I’m pleased to accommodate.
About: I have taken care of dogs (during the day and overnight stays) ranging from 6 months to over two years. In addition to my pet sitting experiences, I have volunteered at two humane societies and specialized with the dogs. Before interacting with the dogs at the humane societies, I completed 22.5 hours of formal training, background security checks, and the Fear Free Shelter Program Core Modules. My responsibilities as a volunteer were canine enrichment activities (including making toys and interactions with dogs), recording behavioral observations, and canine handling onsite and offsite. I also enjoy running, so if your dog is up for that, they are more than welcome to join! I frequent run clubs with dogs because I love being around them and I don't have the finances to take care of my own right now (I am a graduate student). I just graduated from W&M with my Master’s in Science. I am currently job searching so my schedule is very open and flexible. Check my calendar to see when I’m can house/pet sit! At this time, I am only caring for pets in their homes. I am renting my current residence, so I cannot care for pets in my own home.
About: I’ve taken care of all kinds of animals since I was 12. I’ve worked on a farm caring for horses since I was a child. I’ve watched dogs, cats, rabbits, and fish for friends and neighbors. No animal is too small or large for me to love! I rescued my own dog three years ago and now have experience in R+ (positive reinforcement) training. I’d love to practice loose leash walking with your dog. I love taking my dog for long walks and hikes, if your dog likes company I’d love to take them together! I’m experienced in administering medicines, caring for puppies, and senior dogs. I work full time so I’m mostly available on weekends and weekday evenings. I have a car and can get myself anywhere in the Williamsburg area pretty easily. I’ll always do my best to make sure your pet is well taken care of. I understand dog’s body language, and am meticulous in making sure your pets needs are met.
“Alyssa has been wonderful! She walked my Lucie 🐶 for the past few weeks to keep her active while I’m gone to work. Lucie and I are very happy 😊 with her service. After each walk she cleaned her paws and make sure she had water and food available.”
“Caroline walked our dog while we were out of town. I didn’t get the chance to meet her in person but she was prompt and kind. This was our first experience using the rover app and I have complete confidence in using Caroline in the future! I feel much more at ease going out of town knowing that our energetic puppy is being cared for by a sweet girl like Caroline. Thank you so much for helping us out!!”
About: I’ve been around cats and dogs since I was barely tall enough to see over a food bowl, and that lifelong hands-on experience shaped me into someone who naturally understands animal behavior, routines, and training. I’ve personally trained my own dogs and have always been deeply involved in their care, from daily structure to behavior shaping and enrichment. Right now I share my home with a cat who keeps life interesting, and I’m very attentive to creating a happy, stable environment for pets. Animals have always been a constant part of my life, and caring for them feels less like a task and more like second nature. 🐾 My schedule is pretty structured around my work hours: I work 4pm–12am, and outside of that I’m home and available for the rest of the day. I keep my routine simple and steady, and I’m usually around in the mornings and early afternoons before heading into work. I’m not someone who’s constantly on the go or juggling a million commitments—my life is more grounded in work, home, and taking care of my pets. That balance gives me a lot of consistency and time to focus on what matters day to day. I take safety and trust seriously when it comes to animals and their environment. In the past, I’ve crate-trained my dogs and learned how to create calm, structured routines that help them feel secure and well-behaved. I’m comfortable setting boundaries in a gentle but consistent way, depending on the needs of each pet. My home is also very pet-safe, especially because my current cat is extremely curious and determined to investigate everything. I’ve adapted my space to keep hazards out of reach and ensure it’s a safe, enriched environment where pets can explore without getting into trouble. I pay close attention to what they can access and how they interact with their surroundings, so safety is always built into the way I live with animals. 🐾
About: What sets me apart is my calm, attentive approach and experience caring for senior pets and animals who need extra patience, routine, or medication support. I’m reliable, detail-oriented, and respectful of both pets and homes. I follow instructions closely, communicate clearly, and make sure every pet feels safe, comfortable, and loved while you’re away. I work both full time and part time, but pet care fits naturally into my routine. I’m very responsible with scheduling and flexible when it comes to letting dogs out for potty breaks, walks, feeding, and check-ins. I plan my days around pets’ needs and make sure they get consistent care, attention, and companionship while their owners are away. When caring for pets in a client’s home, I stick closely to their usual routines so they feel safe and comfortable. I follow feeding, potty, walk, and medication instructions carefully, provide plenty of attention and companionship, and adjust care based on each pet’s needs and energy level. I’m also respectful of the home and send regular updates for peace of mind
About: I’ve had a medium sized dog for the past eight years. He has always been seen as “my dog,” even though he’s the household dog. I love to take him for walks everyday, car rides often, and play with/treat him! I’m a college junior home for the summer in Williamsburg, VA. I have a part time internship which only requires around 20 hours a week of me being out of the house, so my schedule is very flexible to take care of your babies! In my home specifically, I always ensure my dog is fed, comfortable, and taken care of. I treat my dog as though he has human feelings and speaks english, if you know what I mean. I walk him twice a day and take him for enriching activities often such as car rides. His health is my main priority.
The median cost per walk for dog walking in Winston Terrace is $20
Dog parents share their Rover experiences - Winston Terrace
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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.
Why Choose Rover?
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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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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
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
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winston Terrace sitters!Sitters in Winston Terrace average 3 repeat dog walking clients
FAQs for Dog Walking - Winston Terrace
Frequently asked questions about Rover
The average cost for Dog Walking in Winston Terrace on Rover is $22.2 per walk (as of June 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .
As of June 2026, there are 891 sitters on Rover offering Dog Walking across Winston Terrace. 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 Winston Terrace. 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 Winston Terrace.
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 Winston Terrace. On Rover:
- 95% of walkers can help with special care needs
- 98% can help with giving oral medications or injections
- 98% 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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