Dog Walking Holly Oaks

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Holly Oaks, 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: Brooke H.
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Brooke H.
from
$14
per walk
5.0 out of 5 stars
• 43 reviews
17 repeat clients
26 years of experience
Leonardtown, MD, 20650

“She did great with my pup Scout! He's still a puppy so he can be a lot to handle. She gave him treats when he was good during the walk and she looked for shaded areas since he has thicker hair. Last minute I had to change the time for her to be with Scout because I had something come up and she was very relaxed and open for it! Definitely going to be using her again ❤️”

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Gretchen G.
Sitter Profile Image: Kathryn A.
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Kathryn A.
from
$20
per walk
5.0 out of 5 stars
• 14 reviews
2 repeat clients
30 years of experience
Leonardtown, MD, 20650

About: I’m an experienced, reliable, and responsible pet sitter who truly loves animals. I understand how important it is to have someone you can trust to care for your pets when you’re away, and I treat every pet as if they were my own. I am a stay at home mom of 5 two legged children and 2 four legged children with a background in healthcare. I’m here day and night to help with your pet care needs. I have a large fenced in yard for exercise, and a screened in porch. I can set up a crate if needed. We have 2 large friendly dogs to keep your baby company. Fresh water, regular feeding, medication administration if needed and lots of love! I can guarantee your pup will never get lonely!

Sitter Profile Image: Taylor K.
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Taylor K.
from
$13
per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
2 years of experience
Leonardtown, MD, 20650

About: I grew up with dogs and would help care for them, from walking, to feeding and bathing. I've also helped friends with theirs. I've cared for dogs as small as pugs and dachshunds to as big as collies and pitbulls. I work full time but I do have a very flexible employer! I'm willing to stop by anytime from 8am to 2am and am willing to house-sit as well. I do not offer boarding at my own home but if you asked anyone who knows me theyd tell you that I'm very cleanly, organized and respectful. I will always do my best to adhear to any instructions you leave for your baby and I do have experience kennaling big dogs.

Sitter Profile Image: Caitlin G.
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Caitlin G.
from
$20
per walk
5.0 out of 5 stars
• 70 reviews
17 repeat clients
20 years of experience
California, MD, 20619

“Caitlyn was wonderful with my dad's dog. She was on time, reliable, stayed in good communication with great pics to show how much the dog enjoyed her walk and play time. It was a huge help, since my dad has had health challenges which interfered with good dog walks. Five stars!”

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Shelli L.
Sitter Profile Image: Mya H.
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Mya H.
from
$15
per walk
5.0 out of 5 stars
• 2 reviews
6 years of experience
Leonardtown, MD, 20650

About: Animals are my passion. Big, small, furry, scaly. I have cared for animals for as long as I can remember. I've pet sat my neighbors pets since I was a teenager and I worked at an animal kennel/doggy daycare from the ages of 16-21. And for the past year I have been working in a veterinary hospital as a Veterinary Assistant! I will ensure your pets will be treated as my own, as I consider mine family, and would want others to treat them that way as well! I am currently available as needed, mornings, afternoons, and evenings for your pets. I am willing to stop in later at nights if needed too:) I cannot bring your pet to my place, but I would love to do whatever you need for your fur baby to be cared for the to the best of my ability at your home!

Sitter Profile Image: Adin W.
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Adin W.
from
$17
per walk
5.0 out of 5 stars
• 3 reviews
2 repeat clients
6 years of experience
Charlotte Hall, MD, 20622

About: I have 6 years of hands-on experience caring for my friends and family dogs of all sizes and temperaments, from large breeds like German Shepherds and Pit Bulls to smaller breeds like Yorkies and Corgis. I’m comfortable with energetic dogs, couch loving dogs, playful puppies, and affectionate companions, and I understand the importance of patience, routine, exercise, and making every pet feel safe and cared for while their owner is away. I recently graduated high school so my schedule is very flexible and open to provide routine dependable care for home and your pets while you are away. I always make your pets safety and well being a top priority by keeping pets in a stable safe environment including outside in yards, on walks, as well as inside their home.

Sitter Profile Image: Victoria V.
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Victoria V.
from
$30
per walk
5.0 out of 5 stars
• 61 reviews
21 repeat clients
35 years of experience
California, MD, 20619

“We had a last minute trip and Victoria saved the day. She took great care of our dog Poe who has separation anxiety. She made sure he felt comfortable and safe. She also sent plenty of pictures and reported back on how he was acting on his walks which made us feel more comfortable as well. I’d definitely use her again.”

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Vanessa G.
Sitter Profile Image: Donna K.
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Donna K.
from
$23
per walk
5.0 out of 5 stars
• 26 reviews
10 repeat clients
10 years of experience
California, MD, 20619

“Donna continues to do a great job of walking Mo and taking care of him.”

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Achla S.
Sitter Profile Image: Shemoy S.
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Shemoy S.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
• 38 reviews
16 repeat clients
20 years of experience
California, MD, 20619

“Shemoy did amazing with the pups, and really saved me after a last minute cancellation. Always on time and took lots of pictures. My dogs, who can sometimes be judgey, took to liking Shemoy right away. Definitely recommended as a sitter/walker!”

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Patrick S.
Sitter Profile Image: Tisha R.
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Tisha R.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
10 years of experience
Lexington Park, MD, 20653

About: I love getting dogs out for fresh air and exercise while making sure they always feel safe, comfortable, and cared for. Whether your dog is energetic and playful or prefers a slower, more relaxed pace, I’m happy to match their routine and personality. My goal is to provide plenty of attention, activity, and companionship so your pup stays happy while you’re away. I currently have a very open and flexible schedule while I’m focusing on pattern testing. This gives me plenty of availability for walks, drop-ins, and quality time with your pets throughout the week. My neighborhood is a fenced-in dog park with plenty of lush grass, perfect for safe off-leash play and zoomies! We're also steps away from a private beach and surrounded by scenic trails, so your pup will get lots of exercise, fresh air, and sniffs. I always prioritize safety, positive interactions, and keeping your furry friend happy and comfortable. Water, rest breaks, and lots of love are always included!

Sitter Profile Image: Abi S.
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Abi S.
from
$18
per walk
4 years of experience
Solomons, MD, 20688

About: I have a golden retriever of my own, and have been dog sitting, walking and taking care of other families and friends dogs for about 5 years. I am home from college for the summer, and taking classes at night. I am available during the day and mornings, and have fairly open weekends. I have experience walking pets, feeding them, giving them medication if needed, or just spending time with them while their owners are away! I love sending photos and videos to their owners while they are away.

Sitter Profile Image: Anna O.
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Anna O.
from
$25
per walk
5.0 out of 5 stars
• 1 review
20 years of experience
Lusby, MD, 20657

About: I’ve been taking care of animals for friends, family and coworkers for over 20 years and I’m comfortable with any and all animals. I currently work at a Vet office where animals are my specialty and I’m trusted with others animals. I know of medical terms and how to give basic care until help arrives (if necessary). I pet sit for older people that just need a little bit of extra help, and I’m happy to do it! I love seeing smiles on peoples faces knowing their pups, cats, bunnies, etc are being taken good care of. I have open availability! Open schedule for whenever I’m needed. I have a side job, but I do it when I want to and don’t have a set schedule with that job. I’m self employed basically. I make sure they have water and food whenever they’re scheduled which is usually 8am for breakfast and 4pm for dinner. I don’t let my cats out ever, I don’t really like having cats outdoor like that unless that’s how they were raised. I make sure their litter is clean and taken care of at least twice a day and make sure the dogs are getting walks, pets and snacks. Just making sure the animals are comfortable really is my goal.

Sitter Profile Image: Jennifer M.
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Jennifer M.
from
$28
per walk
13 years of experience
Hughesville, MD, 20637

About: Hi, I’m Jennifer. I’ve been caring for pets professionally since 2013, and I know how much trust it takes to welcome someone into your home and your pet’s routine. Care is built around patient, attentive care. I pay attention to the little things, from a dog’s favorite route to the way a cat likes to be greeted, so visits feel familiar and comfortable. I serve families in Charles, Calvert, and St. Mary’s Counties and are insured through Pet Sitters Associates. Pet care is a big part of my everyday life, both with my own pets and through Waldorf Walkers & Pet Sitting. I plan my week around scheduled walks and visits so each pet gets dependable care and plenty of attention. With over 13 years of professional experience, I understand how much consistency matters. Whether it’s a midday walk or care while their family is away, I make time for each pet’s individual needs—and a little extra love, too! I care for pets in their own homes, where they feel comfortable and can keep their familiar routines. For dog walks, I provide exercise at their pace, time to sniff and explore, fresh water, and plenty of affection. During pet sitting visits, I follow each family’s instructions for feeding, potty breaks, litter box cleaning, playtime, and any special care needs. I pay attention to each pet’s personality and comfort level, whether they’re ready to play or need a little patience to warm up. After each visit, I send photos and an update so you know how your pet is doing. I also treat your home with care and make sure everything is secure before leaving.

Sitter Profile Image: Ryan R.
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Ryan R.
from
$20
per walk
13 years of experience
Lexington park, MD, 20653

About: What sets me apart as a sitter is the level of care, patience, and attention I give to every pet as if they were my own. I understand that every animal has a unique personality, routine, and comfort level, and I take the time to learn what makes them feel safe and happy. I’m especially comfortable caring for puppies I also grew up taking care of English bulldogs and understand the importance of consistency with potty training, basic commands, and positive reinforcement. I’m also attentive and gentle with senior pets, making sure they receive extra patience, medication support if needed, and a calm environment. I’m reliable, communicative, and always keep pet parents updated with photos and messages for peace of mind. My goal is to make sure your pet feels loved, secure, and well cared for while you’re away My schedule is pretty open. I am always flexible depending on what I have scheduled. I do work but only part time. I make time for the pets I watch. I love to take my dog on walks my animals are house dogs they spend time with me and enjoying life not in a cage though they do have one and love to just lay in there but there environment is safe and welcoming.

Sitter Profile Image: Chailyn M.
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Chailyn M.
from
$15
per walk
2 repeat clients
5 years of experience
White plains, MD, 20695

About: I have several years of experience providing dependable and compassionate pet care for dogs of all sizes, breeds, and personalities. I have cared for both small and large adult dogs through regular walks, drop-in visits, and pet sitting, ensuring they receive the exercise, attention, and care they need. I am comfortable handling energetic, strong dogs as well as senior dogs that require a gentler approach. My priority is always the safety, happiness, and well-being of every dog, and I treat each pet with the same love and care I would give my own. I am currently working part-time so I have plenty of time to check in on pets. Prefer morning walks and late afternoon walks.Have an open schedule. When caring for pets in clients’ homes, I make sure they stay comfortable by following their regular routines. I provide fresh food and water, take dogs on walks, let them outside for bathroom breaks, clean up after them, administer medication if instructed, and spend quality time playing with and comforting them. I also keep the home clean and secure by bringing in mail or packages if requested, watering plants, and ensuring doors and gates are locked before leaving. My goal is to give pet owners peace of mind by providing reliable, attentive, and loving care while they are away.

Sitter Profile Image: Trina F.
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Trina F.
from
$18
per walk
5.0 out of 5 stars
• 11 reviews
3 repeat clients
20 years of experience
Waldorf, MD, 20601

“Trina has been amazing with Nugget who is NOT a fan of walking. She has been resourceful to ensure he gets the most out of his walks. She is on time, communicative and provides a thorough report after each walk.”

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Anitra S.
Sitter Profile Image: Alexia M.
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Alexia M.
from
$25
per walk
5.0 out of 5 stars
• 4 reviews
3 years of experience
La Plata, MD, 20646

About: I have hands-on experience caring for a wide variety of animals and feel very comfortable handling pets with different needs and personalities. I currently work in recreational therapy twice a week, which has helped me develop patience, responsibility, and strong attention to detail skills that carry over into providing safe and attentive pet care. As an online college student, I have a flexible schedule that allows me to give pets the time, consistency, an supervision they deserve. At home, our family has five dogs, so I am very familiar with managing multiple pets at once and maintaining consistent schedules. In addition to daily care, I have experience with overnight dog sitting that includes week-long stays where I handled feeding, walks, playtime and managing pet's normal routines. I have cared for puppies, senior dogs, and cats and I understand how to adjust care depending on energy level and age. I have also taken care of chickens while house sitting, so I am comfortable with a variety of animals beyond just dogs and cats. I am able to drive, which allies me to be available for drop ins, walks, and emergencies if needed. Overall, I am dedicated to making families feel safe with leaving their pets at home and making the pets feel comfortable and cared for while their owners are away. I currently work part time and am an online college student. I work Wednesday and Friday nights from 4pm-9pm. For my college classes I do not have to be on any type of zoom, so I do my course work at my own pace. I provide care in my clients home so pets can stay in a familiar, low-stress environment and maintain their normal routine. I follow all care instructions including feeding schedules, walks, medications if needed, and any specific preferences the owner provides. Safety is my top priority. I make sure doors, gates, and crates are secure and keep pets aware from anything that may be unsafe. I work to build trust with both owners and pets by being consistent, patient, and respectful of each pet's personality. I also have reliable transportation, so if an emergency does arise I can provide additional needs.

Sitter Profile Image: Amanda D.
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Amanda D.
from
$30
per walk
5.0 out of 5 stars
• 7 reviews
2 repeat clients
30 years of experience
North Beach, MD, 20714

About: Promo Code for $40 off first time booking for Pet Owners that it is their first time using Rover- AMANDD61392 Friends and Family call me the animal whisperer. I have had a dog/dogs my whole life. I have taken care of dogs from brand new puppies, to babies that were at the end of their life. I'm currently not working full time away from home, so for any boardings that are on week days or weekends, you and your fur babies are good to go. I do have one small dog at home BUT, if you prefer your dogs to be alone while here, my dog is easily brought to his grandparents house:), which they are always happy about. I will update when my work schedule changes. I have a fenced yard (tall privacy wooden fence with sliding deadbolt), and can easily crate dogs if needed. Any animals would have free range of the house and the yard. Your babies are my babies while I am taking care of them.

Sitter Profile Image: Nia C.
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Nia C.
from
$45
per walk
5.0 out of 5 stars
• 108 reviews
26 repeat clients
6 years of experience
Upper Marlboro, MD, 20772

“Nia popped by to walk our dog while we spent the day in Baltimore. She communicated every step of the way, including a heads up on her estimated time of arrival, a progress report(pee,poop, water break) with photos and she called me to let me know I could close the garage door remotely so that we didn’t leave it open too long. We will definitely be calling Nia again!!”

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Molly M.
Sitter Profile Image: Jai B.
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Jai B.
from
$10
per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
1 year of experience
Bowie, MD, 20716

“Jai was amazing. Very professional. I appreciated her communication and timely arrivals. She was great with my dog and I know I will request her for future service.”

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Tracey B.
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The median cost per walk for dog walking in Holly Oaks is $20

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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.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book dog walking

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
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Popular requests for dog walking - Holly Oaks

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Sitters in Holly Oaks average 3
repeat dog walking clients

FAQs for Dog Walking - Holly Oaks

Frequently asked questions about Rover

The average cost of Dog Walking in Holly Oaks is $14 per walk as of October 2026. Most bookings cost between $13 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 733 sitters on Rover offering Dog Walking across Holly Oaks. 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 Holly Oaks. 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 Holly Oaks 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 Holly Oaks. On Rover:

  • 91% of walkers can help with special care needs
  • 93% can help with giving oral medications or injections
  • 97% 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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