Dog Walkers in Winston Terrace, VA

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Top rated Winston Terrace dog walkers

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Amy C.
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Amy C.
from
$18
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
22 years of experience
Williamsburg, VA, 23185

About: I am a grad student with a very flexible schedule! I have owned and cared for a range of dog breeds, from cocker spaniels to German shepherds. I even had a Great Dane for several years! No mess is too big! I’ve administered medications and love getting outdoors and would love to walk or drop into your pet! I adore cats and I have an American bobtail cat called Atlas 🐈‍⬛ My daily routine is incredibly flexible as I am currently working on my PhD! I pick my hours and I can work around any pet sitting/walking needs! I am a gentle person who loves to give pets and go for walks and (if willing) give belly rubs! I look after a very content male cat daily (who follows me around the house).

Sitter Profile Image: Natalie T.
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Natalie T.
Star Sitter
from
$20
per walk
4.9 out of 5 stars
40 reviews
10 repeat clients
15 years of experience
Williamsburg, VA, 23185

Natalie is fantastic. She was so responsive and was able to help us out last minute. You can tell how much she loves dogs and my dog loves her.

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Hannah F.
Sitter Profile Image: Javiera H.
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Javiera H.
from
$13
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
15 years of experience
Williamsburg, VA, 23185

About: I grew up with two dogs. Over the years I've cared for and walked many dogs, and I now share my home with two cats of my own. I have an open summer schedule, so pet care fits in perfectly. I have plenty of time and flexibility to accommodate any requests that come my way. I care for my two cats daily in my apartment, keeping a clean and comfortable environment. I feed them, groom them, clean the litter box, and make sure they get plenty of playtime. For every pet parent, I follow their instructions and adapt to their pet's individual routine and needs.

Sitter Profile Image: Honey H.
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Honey H.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
261 reviews
44 repeat clients
30 years of experience
Williamsburg, VA, 23185

Honey is wonderful with Honey! She sends me pictures and gives me a report on how Ciara is doing daily! Also, was very generous in giving Ciara more time mid week. I recommend Honey highly to my friends!! Thanks Honey ❤️

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Margaret W.
Sitter Profile Image: Victoria L.
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Victoria L.
from
$20
per walk
5.0 out of 5 stars
52 reviews
24 repeat clients
6 years of experience
Williamsburg, VA, 23185

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 :)

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Savannah O.
Sitter Profile Image: Hadley K.
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Hadley K.
from
$20
per walk
5.0 out of 5 stars
7 reviews
1 repeat client
8 years of experience
Williamsburg, VA, 23185

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! :)

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Mary Carter S.
Sitter Profile Image: Therese B.
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Therese B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
94 reviews
23 repeat clients
20 years of experience
Williamsburg, VA, 23185

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.

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Jo Ann H.
Sitter Profile Image: Tori G.
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Tori G.
from
$18
per walk
4.9 out of 5 stars
10 reviews
4 repeat clients
9 years of experience
Williamsburg, VA, 23188

Wonderful service and communication. Highly recommend.

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Mary Carter S.
Sitter Profile Image: Michaela B.
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Michaela B.
from
$20
per walk
8 years of experience
Williamsburg, VA, 23185

About: I've loved animals for as long as I can remember and have been helping care for pets since my early teens. Growing up, I would help care for my grandparents' dogs when they were away, and since becoming an adult I've had dogs of my own and understand the importance of keeping pets happy, safe, and comfortable in their routine. I currently provide drop-in care for a family friend whenever he travels, including feeding, potty breaks, walks, playtime, and making sure his dog receives plenty of attention while he's away. I also previously worked as a Customer Service Representative at a veterinary office, where I interacted with pets and their owners every day. While my role focused on scheduling appointments, assisting clients, and office support, it gave me valuable experience working around animals of all ages, sizes, and personalities. I pride myself on being reliable, communicative, and attentive. I understand that trusting someone with your pet is a big decision, and I will care for your pet as if they were my own. Whether your pet needs a walk, a potty break, playtime, or simply a friendly visit while you're away, I'm happy to help. Pet care is already a regular part of my routine. I care for my own pets daily and currently provide drop-in visits for a family friend when he travels. My schedule is flexible enough to accommodate walks, potty breaks, feeding visits, and check-ins throughout the day. I enjoy spending time with animals and love being able to help pet owners feel confident their pets are well cared for while they're away. When caring for pets in a client's home, I strive to keep them on their normal routine as much as possible. Depending on their needs, this may include feeding, fresh water, potty breaks, walks, playtime, administering treats, and providing plenty of attention and companionship. I understand that every pet is different, so I take the time to learn their routine and preferences to help them feel comfortable while their owner is away. I also make sure to keep owners updated with messages and photos so they can feel confident their pet is happy and well cared for. My goal is to provide dependable, attentive care while treating both the pet and the home with respect. At this time, I primarily offer drop-in visits and dog walking services in the client's home and do not currently offer boarding or overnight stays.

Sitter Profile Image: Hannah M.
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Hannah M.
from
$17
per walk
1 year of experience
Williamsburg, VA, 23185

About: I have taken care of my family's large dogs all my life and volunteered at a local animal shelter for several years, walking, brushing and exercising dogs! I am comfortable with dogs of all shapes, sizes, and energy levels! I am a new graduate nurse, so spending time with animals and getting out of the house is exactly what the doctor ordered! My schedule is flexible, I am available most days that I am not working. I would be happy to walk leash-trained dogs or play with them in a fenced-in environment. I am also available for check-ins, feedings, or socializations for the animals!

Sitter Profile Image: Quinn G.
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Quinn G.
from
$20
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
3 years of experience
Williamsburg, VA, 23185

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 am a graduate student studying billfish. M-F, I am typically in the lab. The mornings and evenings are flexible, and include running and weight lifting depending on the day. On the weekends, I have my long run and I go to the gym. If there's a social event going on I'll try to make it but my schedule is flexible. I don't have a set routine on the weekends besides waking up early to run. At this time, I am only caring for pets in their homes. Since I am a graduate student and renting my current residence, I cannot care for pets in my own home. Depending on the service, I will come as frequently as needed and/or stay overnight.

Sitter Profile Image: Wilhelmina S.
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Wilhelmina S.
from
$15
per walk
4.8 out of 5 stars
5 reviews
3 repeat clients
6 years of experience
Williamsburg, VA, 23185

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

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Candice J.
Sitter Profile Image: Hailey W.
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Hailey W.
from
$14
per walk
5.0 out of 5 stars
1 review
9 years of experience
Williamsburg, VA, 23188

About: I’ve taken care of dogs and cats since I was 10. My parents taught me how to train kittens and puppies. I love to walk my neighbors’ dogs around the neighborhood and I take care of them when they go on vacation. I currently am working part time so I have plenty of time to watch your pets! I can do any time of the day or overnight, as long as I get notified a week in advance. I currently have a 6 year old yorkie who I trained when he was just 6 weeks old. He is the absolute sweetest and loves other animals. I am perfectly fine to work in any home with dogs and/or cats. I will make them happy in their home.

Sitter Profile Image: Craig S.
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Craig S.
Star Sitter
from
$28
per walk
5.0 out of 5 stars
52 reviews
20 repeat clients
20 years of experience
Williamsburg, VA, 23185

Craig is great! Professional and friendly- I had so much peace of mind knowing my dog was being well taken care of with him. Highly recommend!!

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Alexandra H.
Sitter Profile Image: Alyssa R.
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Alyssa R.
from
$18
per walk
5.0 out of 5 stars
17 reviews
4 repeat clients
2 years of experience
Williamsburg, VA, 23188

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.

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Ana C.
Sitter Profile Image: Carissa L.
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Carissa L.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
41 reviews
13 repeat clients
14 years of experience
Williamsburg, VA, 23185

Thank you so much for giving our sweet pup while we’re gone, we were really worried about her being all cooped up while we were out of town and you put all of our worries at ease :) thank you so so much!

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Killian M.
Sitter Profile Image: Caroline B.
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Caroline B.
from
$20
per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
8 years of experience
Williamsburg, VA, 23185

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!!

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Katie M.
Sitter Profile Image: Chelsea W.
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Chelsea W.
from
$17
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
12 years of experience
Williamsburg, VA, 23185

Chelsea is very reliable and flexibile. We appreciate her willingness to adjust on the fly and level of communication! Envy is always happy to see her (:

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C S.
Sitter Profile Image: Lauren K.
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Lauren K.
from
$18
per walk
4.8 out of 5 stars
18 reviews
9 repeat clients
17 years of experience
Williamsburg, VA, 23188

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. I’m easily Google-able and have worked for many public officials who can vouch for me. 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.

Sitter Profile Image: Juliet I.
Verified Background Check
Juliet I.
from
$18
per walk
4.9 out of 5 stars
72 reviews
9 repeat clients
19 years of experience
Williamsburg, VA, 23185

Juliet is amazing!! She was able to show up last minute when we needed her!

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natalie D.
1 / 1
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Winston Terrace dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Michele was fantastic and did such a wonderful job. My dogs were so calm and happy when I came home! Thank you for everything, Michele!

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Margaret C.
Dog Walking
5.0 out of 5 stars

Daniella was very nice, obviously bright and diligent, and kind to Clove. I will ask her again for help. I highly recommend her.

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Mae K.
Dog Walking
5.0 out of 5 stars

Tess is always fantastic and makes me feel so secure that my dogs are always in good and loving hands!!! I am so thankful for her!

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Margaret C.
Dog Walking
5.0 out of 5 stars

Honey is the absolute best! So incrediblely thorough and takes wonderful care of our dogs! We are so grateful for her.

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Lily S.
Dog Walking
5.0 out of 5 stars

Kayla was perfect for our lovable but sometimes unpredictable dog. They bonded immediately in a meet and greet. They walked and played fetch. Great communication with us for this 5 day care. Will definitely for ask her for our next time away.

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Roger G.
Dog Walking
5.0 out of 5 stars

Jess is awesome! My puppy loves her and she is very nice and responsive. I will definitely book with her again!

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Ellie B.
Dog Walking
5.0 out of 5 stars

Kira came highly recommended by our other rover walker to pick up the days she couldn’t.. she was super great with buddy during their meet and greet. I could not recommend Kira enough

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Justin C.
Dog Walking
5.0 out of 5 stars

Rebecca was punctual and seemed to like Soffie. She is very nice and friendly, and I certainly would like to have her again.

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Lana W.
Dog Walking
5.0 out of 5 stars

Emilie is wonderful! She takes our pup for weekly walks and is reliable, punctual, and has great communication. I highly recommend her!

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Dylan B.
Dog Walking
5.0 out of 5 stars

Katie was great. Fin was excited both meeting her and walking with her. I will definitely reach out aain.

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Susan C.
Dog Walking
5.0 out of 5 stars

Lauren was on time and promptly communicated before and after her visit with Nelson. She was also very helpful with navigating changes to the walking schedule. I highly recommend Lauren and will schedule her in the future.

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Julie S.
Dog Walking
5.0 out of 5 stars

Erin was great with my three dogs. She was punctual, kept in touch and was great with the dogs. Thank you Erin.

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Paige M.
Dog Walking
5.0 out of 5 stars

Wonderful walker and Peyton loved her. He looked forward to seeing hee every morning. I highly recommend Caroline to anyone.

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Debbie W.
Dog Walking
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The median cost per walk for dog walking in Winston Terrace is $20

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Sitters in Winston Terrace average 3
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Winston Terrace on Rover as of Jun 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Winston Terrace dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 669 dog walkers in Winston Terrace. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 85% of Winston Terrace dog walkers respond in under an hour.

Dog walkers in Winston Terrace have an average of 16 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Winston Terrace.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 669 dog walkers in Winston Terrace on Rover, so you’re sure to find the perfect match for your dog! In Winston Terrace, 94% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.