Dog Walking Osborn Landing

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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: Victoria C.
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Victoria C.
from
$20
per walk
5.0 out of 5 stars
10 reviews
1 repeat client
17 years of experience
New Kent, VA, 23124

Victoria was a blessing! I work shift work at a hospital and have to leave early for work. She always took great care of my sweet fur baby. Once summer is over and my oldest can’t walk her anymore I’ll have to hope she is free to come back!

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Kristjana S.
Sitter Profile Image: Rebecca G.
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Rebecca G.
from
$20
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
28 years of experience
New Kent, VA, 23124

Rebecca has an awesome attitude and Kitchi adores her!

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Victoria B.
Sitter Profile Image: Stephanie M.
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Stephanie M.
from
$16
per walk
10 years of experience
Providence Forge, VA, 23140

About: Hello! I have spent years providing love and care for my family pets as well as those of friends and neighbors. I know how special your pet is to you and I’m happy to help care for them however I can. Whether it’s checking in on a pet while you’re out of town or taking them for a stroll when you’re stuck at work, I’d love to step in any time you’re not available. My schedule is flexible and negotiable. I’m always careful and considerate when coming to your home and will be sure to follow any specific requests you have for your furry friend. I look forward to having the change to use my experience to care for your pet as though they’re my own!

Sitter Profile Image: Sandra T.
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Sandra T.
from
$20
per walk
5.0 out of 5 stars
9 reviews
1 repeat client
15 years of experience
Toano, VA, 23168

About: Hi, I’m Sandra! Animals have always been a huge part of my life, and caring for pets is something I love. I know every pet has their own personality, routine, and comfort level so I take the time to make sure they feel safe, happy, and loved while you’re away. Whether your dog is full of energy and ready for long walks and playtime, or your senior pet prefers a slower pace with extra patience and gentle care, I adapt to their individual needs. You can count on me to provide dependable care, regular updates, and plenty of love while you’re away. I’m a stay at home mom and have all the time in the world to spend with the pets in my care. I also enjoy gardening, baking, pottery, walks and spending time with my family. We have a doggie gate and big fenced backyard for your dog to run and play outside. Pets are welcome on the couch so we can all watch movies together. We don’t crate unless specifically requested by clients and we typically go on 2/3 walks a day.

Sitter Profile Image: Aneesa R.
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Aneesa R.
from
$15
per walk
5.0 out of 5 stars
4 reviews
9 years of experience
Toano, VA, 23168

About: I started volunteering at the Humane Society at the age of 11, where I fell in love with caring for animals. I lived on a base where people traveled frequently and I was trusted to keep their pets safe and looked after. I now work at a dog daycare/ boarding facility as a kennel attendant, so I have the proper training to take care of your pets. I enjoy my job and have lots of love to give to animals! My schedule is very flexible. I have a two hour lunch break when I do work, and I only work part time. I am a college student and even with next semester coming up, I still will be very available. Unfortunately, I am unavaible at the moment for boarding at my house because of the pets in my household. Hopefully in the near future I will be able to!

Sitter Profile Image: Victoria L.
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Victoria L.
from
$20
per walk
5.0 out of 5 stars
52 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: Hope G.
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Hope G.
from
$16
per walk
10 years of experience
Quinton, VA, 23141

About: I've been taking care of dogs and cats for as long as I can remember. Many of my neighbors would often ask me to take care of their pets while they're away, and I still watch all of them to this day! It gave me quite a lot of experience with different types of animals among all ages too. All of their amazing pets have inspired me to join Rover to meet many more, and hopefully, I can one day get a dog of my own! I'm currently on summer break for college with no part-time job, so my schedule is completely free and flexible for any sort of pet or home needs. I take utmost care of pets as they are just as important as people! As a dog owner myself, I love on them and go above and beyond when taking care of them. Aside from just feeding or walking, I love playing and spending time with other animals as I believe they all need proper attention and not just their basic needs met while their owners are away!

Sitter Profile Image: Lucas B.
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Lucas B.
from
$16
per walk
5 years of experience
Quinton, VA, 23141

About: I have had many pets in my life ranging from dogs and cats, to turtles and parakeets. With this, I can promise I am used to all the different personalities pets can offer. Whether they are energetic or apathetic I can promise you your pet is in safe hands. I am currently on break from college and am doing this as a way to make some extra money. I also play semi-professional soccer in Richmond, Va so I schedule any dog care activities around any practices or games. As a pet owner myself, I can follow any special instructions that are required for your pet. Whether its giving medication, feeding instructions, walking habits, etc. I promise to prioritize your pets needs as if they were my own.

Sitter Profile Image: Alyssa D.
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Alyssa D.
from
$20
per walk
5.0 out of 5 stars
10 reviews
3 repeat clients
9 years of experience
West Point, VA, 23181

About: Hi! I currently have a boxer/shiba Inu and a rescue puppy. My boxer/shiba went through an intensive training program where I was taught how to train a dog as well so I’m great with dogs. I love dogs (maybe more than people lol) and whenever there’s a dog around me my heart melts and I just want to play with them and take care of all the pups!! I am currently a teacher and work Monday-Friday. I walk and/ or feed the pets I’m worked with before work and then again after work as well as play time. In the weekends I’m home all day long as well as in the summer months. I care for all animals as if they were my own. All animal get attention, scheduled meals, and exercise. I also have gates to separate animals if necessary.

Sitter Profile Image: Christina S.
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Christina S.
Star Sitter
from
$40
per walk
5.0 out of 5 stars
239 reviews
112 repeat clients
15 years of experience
Toano, VA, 23168

Gave lots of feedback and answered all of my questions while gone. Oliver warmed up to her over the weekend and everything was in place when I came home. Great job will definitely book again.

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Kodi M.
Sitter Profile Image: Briar B.
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Briar B.
from
$20
per walk
5.0 out of 5 stars
6 reviews
4 repeat clients
6 years of experience
West Point, VA, 23181

About: I've been taking care of dogs since I was little. I adore all breeds, ages, and sizes. I'm very attentive, and genuinely enjoy spending time with dogs. I currently work at a dog pet resort, so I have plenty of experiences with all sorts of dogs. I currently work part time, and am available pretty often! My scheduling is flexible, and I'm very transparent about my availabilities. I prefer to work daylight hours, but thats not a hard rule for me. I've been interacting with dogs of various temperments for a long time, so I'm practiced at providing a safe environment for your dogs. I'm very respectful of any safety rules you may have, and will never cut corners when it comes to the well-being of your pup.

Sitter Profile Image: Jessica F.
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Jessica F.
from
$20
per walk
33 years of experience
West Point, VA, 23181

About: I've been caring for animals since I was 7 years old, and my love for pets has only grown over the years. As an adult, I worked at an animal shelter, where I gained hands-on experience caring for dogs with a wide range of personalities, needs, and backgrounds. I have also adopted and cared for three dogs of my own throughout every stage of their lives, from energetic puppies to senior dogs requiring extra patience, attention, and specialized care. This experience has given me a strong understanding of daily pet care, administering medications, recognizing changes in behavior, and providing the love and comfort pets need to feel safe and happy. I treat every pet as if they were my own and understand how important it is to find someone trustworthy to care for your furry family members. Whether your pet needs a long walk, playtime, companionship, or extra attention due to age or special needs, I am committed to providing reliable, compassionate care while you're away. I am currently in between jobs, which gives me plenty of flexibility and time to provide your pets with the attention, care, and companionship they deserve. Whether your furry family member enjoys playtime, walks, cuddles, or simply having someone nearby, I can tailor my care to their individual needs and routine. As a lifelong pet owner with experience caring for both dogs and cats of all ages, I understand how important it is to ensure pets feel safe, comfortable, and loved while you're away. From energetic puppies and playful kittens to senior pets who need a little extra patience and care, I am committed to treating every animal as if they were my own. I have a fully fenced backyard with a 5-foot chain-link fence, providing a safe and secure space for your pet to play, explore, and enjoy the outdoors. I do not have neighbors directly adjacent to my yard, so there is minimal concern about pets being distracted or stressed by animals on the other side of the fence. I am a lifelong animal lover and currently share my home with a senior dog, whom I've raised since she was 8 weeks old, and a young cat who has been part of our family since he was 8 weeks old as well. Having cared for pets through every stage of life—from playful puppies and kittens to senior pets requiring extra attention—I understand that every animal has unique needs and routines. When your pet stays with me, they will be treated like a member of the family. My goal is to provide a safe, comfortable, and loving environment where they can feel at home while you're away. I personally allow my pets on the furniture, but I fully respect each owner's preferences. If your pet has specific rules, routines, feeding schedules, medication needs, or restrictions, just let me know and I will be happy to follow them to ensure consistency and comfort during their stay. I believe communication is important, so I am also happy to provide updates, photos, and messages while your pet is in my care, giving you peace of mind knowing they are safe, happy, and well loved.

Sitter Profile Image: Jade N.
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Jade N.
from
$16
per walk
5 years of experience
Williamsburg, VA, 23188

About: I've taken care of animals of all kinds, from dogs and cats to chickens, ducks, and goats, since I was 13. In my senior year of high school, I took a veterinary science class where I did check-ups and grooming on all sorts of animals. (Dogs, cats, bunnies, guinea pigs, etc.) I feed, walk, and medicate animals for coworkers, family, and friends just about everytime I'm home from school! I plan on working part-time, so I will have limited times during the day to walk your dogs, but I will have plenty of time to go over and feed, medicate, play, empty litter, etc., after or before my shifts! We've got a super big yard, so plenty of room to run around and play. My doggies at home use an electric fence, but I'm used to walking other dogs on a leash, no problem! Additionally, my pups get along well with other dogs, so no issues in regard to company and territory!

Sitter Profile Image: laneise B.
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laneise B.
from
$25
per walk
5.0 out of 5 stars
1 review
40 years of experience
Quinton, VA, 23141

About: Any day any time I’m here to help you with your pets needs. Several local referrals and references to provide you and your loved ones. I provide pet services everyday. All hours of the day including overnights. No need to worry just contact me. I have and breed dogs as well. Animals are always my first priority. They are treated as my own. My children play an active roll in helping with care of our furry friends.

Sitter Profile Image: Chelsea W.
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Chelsea W.
from
$20
per walk
5.0 out of 5 stars
11 reviews
2 repeat clients
14 years of experience
New Kent, VA, 23124

About: I believe that all fur babies deserve to be spoiled just as I spoil my own! I love to give treats and usually have dog treats with me anywhere I go. I do have a full time job but I have a very flexible schedule and work from home. I begin my visits as early as 630 am and can do visits until 10pm in the evening. I work from home so I can adjust my schedule to accommodate your needs. I have open availability on the weekends. I know the stress being away from my furbaby in the past I couldn't relax because I worried about her safety the whole time I was gone. Which is why I keep you in the loop about your pet when they are in my care, you won't have to hunt me down to make sure they are having fun. We make sure that we practice safe departures so that your dog is safe and

Sitter Profile Image: Teona & Louelyn M.
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Teona & Louelyn M.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
171 reviews
51 repeat clients
17 years of experience
Williamsburg, VA, 23188

About: Hi, we’re Teona and Louie! We’re passionate about caring for dogs of all ages, sizes, and personalities. With two gentle, well-socialized pups of our own, we know how important it is for dogs to feel safe, comfortable, and loved while their owners are away. We have hands-on experience with: • Puppy training & socialization – helping young dogs learn basic commands, crate training, and good manners. • Senior dog care – providing extra patience, gentle handling, medication administration, and accommodations for mobility or health needs. • Multi-dog households – managing playtime, feeding schedules, and safe introductions so everyone gets along. • Special care needs – whether it’s dietary restrictions, anxiety management, or post-surgery recovery. Our goal is to give owners peace of mind knowing their furry friends are in experienced, caring hands. I’m home most of the time, except for quick grocery trips. I’ll be available to give your dog plenty of attention and care throughout the day. We keep your pups active during the day so they’re ready to settle in at night. Dogs usually sleep in their room with their own bed or blanket (if provided), which keeps them safe and cozy. We have a separate room to ensure they’re comfortable and relaxed. Feel free to message us with any questions—we’d love to make sure both you and your pup feel at ease!

Sitter Profile Image: Ethel S.
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Ethel S.
from
$55
per walk
5.0 out of 5 stars
22 reviews
3 repeat clients
40 years of experience
Williamsburg, VA, 23188

About: I have grown up with animals. Dogs and cats are at the top of the list. I've been around domesticated animals all of my life. My first kittens at my young age was two siames kittens Who had 2 litters of kittens as well as having to toy poodle dogs, that had two litters of puppies twice. I must have been about 10 so it was from then that I have been loving & caring for fur babies.. Though I do not Own a dog or a cat right now, but look forward to owning some in my future.. I currently own a guinea pig. I just recently experienced the end of a pug/fur baby end of life. I took care of the pug for his last six months of life. Soon after that I boarded a beautiful pitbull for the weekend of mother's day. So to book with me, i'm sure I will have you covered.. Because I am home during the day I am a great fit for you fur baby. I love on your Fur baby while you are on occasion or just I'll have an a fun day. Because I am located across from freedom park in James City County, Williamsburg. I feel i'm in a great place to be able to get them out to go for walks and just run and play.

Sitter Profile Image: Joseph W.
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Joseph W.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
11 reviews
3 repeat clients
5 years of experience
Chester, VA, 23836

Joseph does a great job with my feisty pup.

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Connie C.
Sitter Profile Image: Ryan M.
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Ryan M.
from
$30
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
6 years of experience
Williamsburg, VA, 23188

Ryan was great! Super friendly and professional. Would definitely book again.

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Liam P.
Sitter Profile Image: Sarah S.
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Sarah S.
from
$16
per walk
20 years of experience
Henrico, VA, 23231

About: I offer personalized, one-on-one care tailored to your dog’s unique needs, personality, and routine. With a focus on reliability and attentiveness, I make your dog’s comfort and daily schedule a priority. I strive to be a calm, loving presence your dog can trust, helping them feel safe, relaxed, and cared for while you’re away. As a full-time teacher, my weekdays follow a consistent and predictable schedule. I am available for afternoon visits after school, evening care, as well as overnight stays when needed. On weekends, holidays, and school breaks, I have more flexibility and can provide extended care, additional visits, or longer stays. This structure allows me to offer reliable, attentive pet care while maintaining clear communication and consistency for your pet. I care for pets with a focus on comfort, routine, and individual needs, whether in my home or in my client’s home. I follow each pet’s normal schedule for feeding, walks, playtime, and medication, and I take time to learn their preferences and personality. In a client’s home, I respect their space while providing attentive, one-on-one care and keeping pets in a familiar environment. I prioritize safety, cleanliness, and calm interactions, and I communicate regularly with updates so owners can feel confident their pet is happy and well cared for.

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The median cost per walk for dog walking in Osborn Landing is $20

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Sitters in Osborn Landing average 3
repeat dog walking clients

FAQs for Dog Walking - Osborn Landing

Frequently asked questions about Rover

As of June 2026, there are 2,002 sitters on Rover offering Dog Walking across Osborn Landing. 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 Osborn Landing. 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 Osborn Landing.

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 Osborn Landing. On Rover:

  • 94% 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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