Dog Walking Winston Terrace

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Over 46
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.

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Sitter Profile Image: Rhianna M.
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Rhianna M.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
17 reviews
4 repeat clients
5 years of experience
Williamsburg, VA, 23185

Great service and communication! Appreciate her good help with our dog.

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Mary Carter S.
Sitter Profile Image: Kendall K.
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Kendall K.
from
$12
per walk
7 years of experience
Williamsburg, VA, 23185

About: I have had pets my entire life - dogs, cats, guinea pigs, fish, hamsters, and more. I adore animals, and do everything I can to help each and every one of them. I am a student - outside of class, my schedule is pretty flexible. I am able to dedicate parts of my day to taking care of your animals! I treat animals in any location with respect and love. I do everything I can for my own pets, and will do the same for yours.

Sitter Profile Image: Lauren K.
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Lauren K.
from
$15
per walk
4.8 out of 5 stars
20 reviews
14 repeat clients
17 years of experience
Williamsburg, VA, 23188

Lauren does very good work. She's clearly quite competent with Clove and concerned about her welfare. She's pleasant for conversation afterwards and is flexible. I recommend her highly.

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Mae K.
Sitter Profile Image: Therese B.
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Therese B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
110 reviews
26 repeat clients
20 years of experience
Williamsburg, VA, 23185

The beagles love Tess! She is very quick to respond and observant to notice if either one of my pups seems off. We are so lucky to have her take care of them!

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Colleen N.
Sitter Profile Image: Alesscia C.
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Alesscia C.
from
$22
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
18 years of experience
Williamsburg, VA, 23185

About: I have loved animals all my life, and my experience has ranged from caring for my own pets, to short-term and long-term fostering for friends and military families. I have cared for dogs, cats, hamsters, lizards, bunnies, birds and small livestock. I love them and treat them all as though they are my own. I am currently a currently a stay at home mom, and my children are now all school-aged. I care for my animals at home, and I have an open schedule, heart, and home to care for other animals. I have a about 1.3 acres of land with a dedicated (vinyl) fenced in area for dogs so I have plenty of room for outdoor playtime. Indoors, a few of my animals are crated at night based on their individual needs but all walk freely during the day. In your home, I am open to whatever is most comfortable for your pet.

Sitter Profile Image: Lauren W.
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Lauren W.
from
$20
per walk
5.0 out of 5 stars
23 reviews
3 repeat clients
25 years of experience
Williamsburg, VA, 23188

Lauren is fantastic at sending pictures and taking wonderful care of my Shelby!

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Erin B.
Sitter Profile Image: Tori G.
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Tori G.
from
$18
per walk
4.9 out of 5 stars
11 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: Tanti B.
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Tanti B.
from
$20
per walk
3 years of experience
Williamsburg, VA, 23185

About: I’ve been watching both cats and dogs for friends and neighbors for a few years now, and now that I have more flexibility in my schedule I would love to provide my services to others! I work fully remotely and have a ton of flexibility to take care of your pets! If i’m not on vacation, i’m usually free to help :) I live in an apartment with my two-year-old chihuahua mix, Archie! Plenty of opportunities to run around the fenced dog area or ride over to a trail or park for more activity.

Sitter Profile Image: Matthew C.
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Matthew C.
from
$20
per walk
5.0 out of 5 stars
3 reviews
15 years of experience
Williamsburg, VA, 23185

About: Ever sense I was a kid I've loved taking care of any animal under the sun, and I still do. When I got my first dog I was so excited and loved him no matter what. I am currently not working so I have all the time in the world for your pets. I am avaliable on weekdays at anytime and will give your pets the attention they want. I can give all of my attention to your pets and make them feel happy and excited or the opposite where both of us can relax and enjoy eachothers company.

Sitter Profile Image: Craig S.
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Craig S.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
58 reviews
23 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: Trey C.
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Trey C.
from
$12
per walk
10 years of experience
Williamsburg, VA, 23188

About: I’ve taken care of my families Labs and Golden Retrievers for many years. I’ve also pet sit at friends houses and taken care of cats and many different breeds of dogs. I’m looking for this to be my part time work while I take summer classes. I like to work out in the mornings but I am free all afternoon, and can be available in the mornings if needed. I also walk dogs on a leash and treat any dogs like they’re my own. I have 3 golden retrievers at home that are apart of my family and I will treat your pets with the same care.

Sitter Profile Image: Victoria L.
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Victoria L.
from
$20
per walk
5.0 out of 5 stars
53 reviews
26 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: Nicole M.
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Nicole M.
from
$20
per walk
5.0 out of 5 stars
41 reviews
20 repeat clients
20 years of experience
williamsburg, VA, 23185

Nicole went above and beyond to take care of our boy while we were out on vacation for 2 weeks. She is sweet, reliable and communicative. Our dog is forever in love with her. I would absolutely recommend her to anyone looking for a good walker/sitter.

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Juan N.
Sitter Profile Image: Mary G.
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Mary G.
from
$22
per walk
5.0 out of 5 stars
134 reviews
45 repeat clients
16 years of experience
Williamsburg, VA, 23185

Mary was ABSOLUTELY AMAZING!!! Yesterday she took care of our dogs all day during our wedding. She checked in on them three times and even delivered our dogs to our wedding venue so our brother could walk our dogs down the aisle during the ceremony. She hung out for the wedding, and then delivered them back to our hotel. She was so pleasant, followed every recommendation and request we made, and our dogs were so well cared for! She even went above and beyond walking the dogs for a long time before and after the wedding! If we lived locally in Newport News we would DEFINITELY us her again. I highly recommend her and her services!

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Stephanie G.
Sitter Profile Image: Olivia S.
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Olivia S.
from
$20
per walk
5.0 out of 5 stars
18 reviews
5 repeat clients
5 years of experience
Williamsburg, VA, 23185

So great with my corgi! He loved her

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Ashley E.
Sitter Profile Image: Kate G.
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Kate G.
from
$16
per walk
5.0 out of 5 stars
3 reviews
21 years of experience
Williamsburg, VA, 23186

About: Worked as a veterinary assistant and have experience caring for cats, dogs, reptiles, horses, and farm animals. Also have experience working with scared or aggressive animals I am a student, so I have a flexible schedule and would love to care for animals during study breaks to make some extra money I always am thoughtful about the animals and pay lots of attention to what they need and are telling me. I make sure the animal is comfortable and happy

Sitter Profile Image: Sarah H.
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Sarah H.
from
$22
per walk
5.0 out of 5 stars
3 reviews
3 years of experience
Williamsburg, VA, 23188

About: I believe dogs are the purest of friends we can find on this earth and will cherish your pup as if it were my own. I am warm, prompt, communicative, and will happily send photos and videos of your dog to reassure you that all is well! I know how stressful leaving your dog at home can be, and will be accessible and receptive to any level of communication that you need. I am here to not only care your pup, but also help keep your own anxiety at bay! I am from a family of die-hard yellow lab lovers and am current sister to 7 year old yellow lab named Theo. Our favorite activities together are hide and seek with treats or toys, and evening massages to help him calm down before bedtime. Your dog will be equally loved by me! I am a graduate student in my final semester and am working part time entirely from the home. I have ample time to tend to your pet with snuggles and long walks outside! Theo dog featured in my profile picture is a family dog, who does not live with me currently. So my attention is 100% for your pup! I live in a very dog-friendly apartment complex in the Barton Springs/Bluffs area, right by the Greenbelt trailhead. My apartment is ground level and opens up onto an unfenced yard area perfect for potty breaks. My studio apartment is approx. 450 square feet, so pretty small but your dog is welcome to have free reign on the couch and bed (if they are allowed to do so in their own home, of course!). When I take care of dogs in another person's home, I try to arrange my schedule such that I am never gone for more than 3-4 hours in the entire day. I understand the anxiety pets deal with when their beloved hoomans are away, so I am very committed to adjusting my schedule to prioritize being with the dog as much as possible.

Sitter Profile Image: Lo J.
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Lo J.
from
$25
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
6 years of experience
Williamsburg, VA, 23188

Great with Millie, I’ve seen improvement on Millie’s walks and she comes back in such a happy mood after them!!

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Mckenzie C.
Sitter Profile Image: Emmanuel S.
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Emmanuel S.
from
$16
per walk
5 years of experience
Williamsburg, VA, 23185

About: Every since I got my first cat my life has never been the same. Now I always love to take care of all my pets for my friends and family house sitting and long walks. I'm a college student, so over the summer I have copious amounts of free time that allows me to flexibly take care of pets throughout the day. I ensure that all their primary needs are first satisfied, food, water, and walks, then I like to ensure that they get plenty of attention for the time I'm with them.

Sitter Profile Image: Sally M.
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Sally M.
from
$19
per walk
5.0 out of 5 stars
2 reviews
15 years of experience
Williamsburg, VA, 23188

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.

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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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5.0 out of 5 stars

We were able to book Jared for drop in visit and walk on short notice. He was very responsive and came to meet Rooney prior to visit. He sent pictures and updates after walks. We will definitely book with him again.

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Stacey E.
Dog Walking
5.0 out of 5 stars

Eloise was the best dog walker! She took such great care of my special boy and paid attention to all his quirky needs. My dog is begging for her to come back. Definitely will be booking her again soon!

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Erika G.
Dog Walking
5.0 out of 5 stars

Lauren does very good work. She's clearly quite competent with Clove and concerned about her welfare. She's pleasant for conversation afterwards and is flexible. I recommend her highly.

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Mae K.
Dog Walking
5.0 out of 5 stars

Jessica is so great with our dog, Honey! I have booked with her several times and she is always very reliable, trustworthy, and caring. Honey loves her! I definitely would recommend her to others!

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Andrea K.
Dog Walking
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

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
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Popular requests for dog walking - Winston Terrace

Select a filter and find qualifying sitters offering dog walking.

Sitters in Winston Terrace average 2
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 August 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 August 2026, there are 870 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:

  • 94% of walkers can help with special care needs
  • 96% 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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