Dog Walking Oakwood
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Oakwood, 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.
About: I’ve cared for dogs of all breeds & sizes over the years. I am comfortable with puppies through senior age. Friends, family and clients have relied on me to feed, walk, play with, clean up after, and love their pups as if they were my own. Due to having over 30 years experience working in veterinary medicine, I can administer medications, including injections, and sq fluids. I can practice obedience skills during my visits as well. I’m available for pet care visits on Monday & Tuesday mornings-lunchtime, Wednesday & Thursday mornings as well as evenings, Friday afternoon-evening, and all day on Saturdays and Sundays. I am also available on major holidays. I am very safety conscious and will care for your pets as carefully as I would my own. I will follow whatever your normal household routine is so that your pets feel safe and comfortable. They thrive with routines! If they use a crate, need treats after potty breaks, want belly rubs after a meal, etc., I am there for it all!
“Elizabeth is so reliable and so caring! She will care for your pet as her own. We are so grateful to have found someone to help with our fur baby and someone who loves our pup as much as we do!”
“Andrew did a great job this weekend! He walked my very large Labradoodle and St Bernadoodle and made sure both dogs and my 3 cats were fed and had water. He followed the care instructions, was extremely communicative and arrived promptly at the booking time. I will absolutely be using Andrew for future bookings, highly recommended!!”
“Mae is very reliable, punctual and takes great care of our dog Cannon on their daily walks. She is a great communicator and genuinely loves caring for our dog. I would highly recommend Mae for your dog walking/sitting needs.”
“Laura was great! I made a mistake on the booking date, and she was kind enough to still go by and make sure my babies were taken care of despite my mistake. I will absolutely be working with her again. Highly recommend.”
“Sarah really helped me out, again. Work made it difficult to spend time with my dog for a few days. She took her time with him and kept him active during her visits to make him feel happy in my absence.”
“Great dog walking services. Allison is always responsive and attentive to my dogs needs. She is honest about schedule and timing and I appreciate her for this! My dogs always sleep well after and are happy for their walks with Allison.”
About: Hello! I'm a former VP at a real estate non-profit, transitioning to a new job. I'm available in August and September for drop-in visits, walks, and overnight care. As a resident of Arundel on the Bay neighborhood, I'm available to AOTB, Annapolis Cove, Bay Ridge, and Thomas Point neighborhoods within a 5-7 minute drive. I have no kids, so dogs have always been my 4-legged fur babies. I'm an active volunteer and puppy raiser with Warrior Canine Connections, an organization who trains service and therapy dogs for veterans with visible and non-visible injuries. I currently have 2 dogs of my own. Sookie, a 6 year old pointer mix, and Penny, a 6 year old lab/retriever mix. Both about 70 lbs! Sookie is a handful and I've participated in a few different training programs with her. I've become well versed in many types of dog behaviors, reactivity, fear aggression, and more. I'm calm, patient, warm, and well-versed in managing dogs with different personalities. I've also raised two special needs English Bulldogs, and understand the care required for dogs with medical issues. If you hate the idea of boarding your dog at a strange place when you're away, or have heard bad stories about injuries or neglect at doggy daycares, I'm looking forward to caring for your furry friend in your home! I will make sure your dog gets physical activity, potty breaks, or nap times in the sun. I will be happy to send you pictures, videos, and updates, and will work with you to make sure your dog and/or cat is cared for in a way that makes you and the pet happy! I look forward to meeting you and your furry friend! Most importantly, you can feel safe and secure with me in your home. I'm a former VP at a real estate non-profit, transitioning to a new job. I'm available in August and September for drop-in visits, walks, and overnight care. As a resident of Arundel on the Bay neighborhood, I'm available to AOTB, Annapolis Cove, Bay Ridge, and Thomas Point neighborhoods within a 5-7 minute drive. I have no kids, so dogs have always been my 4-legged fur babies. I'm an active volunteer and puppy raiser with Warrior Canine Connections, an organization who trains service and therapy dogs for veterans with visible and non-visible injuries. I currently have 2 dogs of my own. Sookie, a 6 year old pointer mix, and Penny, a 6 year old lab/retriever mix. Both about 70 lbs! Sookie is a handful and I've participated in a few different training programs with her. I've become well versed in many types of dog behaviors, reactivity, fear aggression, and more. I'm calm, patient, warm, and well-versed in managing dogs with different personalities. I've also raised two special needs English Bulldogs, and understand the care required for dogs with medical issues. If you hate the idea of boarding your dog at a strange place when your away, or have heard the bad stories about injuries or neglect at doggy daycares, I'm looking forward to caring for your furry friend in your home! I I will make sure your dog gets physical activity, potty breaks, or nap times in the sun. I will be happy to send you pictures and videos and updates, and will work with you to make sure your dog and/or cat is cared for in a way that makes you and the pet happy! I look forward to meeting you and your furry friend! I want to make sure you and your pet feel most comfortable. What is their normal routine that will make their time away from their owner more enjoyable? Any tips or tricks to making your pet more comfortable with me, or any special needs, words you use, or special requirements? Do they have any fears, reactivity, dog-aggressions, resource guarding, or other behaviors I should be aware of? I am familiar and well-versed in those behaviors, but the more I know in advance, the better! If you are a new client, I request a complimentary meetup for us to get acquainted.
“Thomas is so good working with our 14 1/2 year old black lab with some serious arthritis. He helps her up the stairs and competently gets her on and off the boat. When Thomas is here, we don’t worry about her while we are away. He goes above and beyond for our old girl with a smile and kind words.”
“Ellie was great! She’s flexible and communicates well which makes it easy to trust her! She also did an outstanding job with my husky lab, Malibu. Would definitely recommend booking!”
“Jessica has been wonderful! I needed help on short notice for my energetic Staffy/Lab mix while I worked overnight shifts, and she exceeded my expectations. She was great with my dog from the very first meet and greet, and clearly has experience handling larger, high-energy dogs. She provided a full 30 minute walk, updates with photos, notes about the visit, and even tracked potty breaks and checked her water. Knowing my dog was getting exercise and attention in the middle of my 12 hour shift made a huge difference and greatly reduced my stress. Jessica has been reliable, professional, communicative, and caring. My dog absolutely loves her, and I feel completely comfortable having her care for my pet. I highly recommend her to anyone looking for a trustworthy and experienced dog walker!”
About: Hi, I’m Hannah! I’ve grown up with dogs my whole life and can’t remember a time when I didn’t have a furry companion by my side. Since my teenage years, I’ve been the go-to pet sitter for friends and family, and I still love helping out whenever I can. I also foster dogs, so I’m experienced with pups of all sizes, temperaments, and needs. Your dog will be in caring, capable hands with me! I am currently working remotely, so I am free most of the day to care for your dog and be there as a friend and make sure they are not left alone. I have a fenced in backyard that your pup can run around in. I also have two sweet and loving dogs of my own that will keep your pup company! If coming to your house, I will respect your space, and let you tell me how to manage your pet and home.
About: Hi! I'm a lifelong dog lover who grew up with 3 dogs, and regularly pet sit for friends and family before deciding to make it official. Friends often call me an animal whisperer because even shy or nervous pets tend to warm up to me quickly. I work remotely, and am very active, so I have a flexible schedule and can give your pet plenty of attention (and activity)! I work remotely and have very flexible hours, so your pet will have plenty of time, walking, snuggling, and being active. I also attend run clubs where pets are allowed, so if your fur baby is social, I’ll happily take them! I have a backyard, and live in a community with plenty areas to walk and sniff. Pets are welcome to be on furniture and in bed! I’m an excellent communicator, and will work collaboratively with you to determine the best care plan for your pet.
About: I grew up around big dogs and cats, so I’m familiar with reading animal behavior. Dog walker and cat socialization volunteer at local animal shelter near college. I’m currently taking a class that meets Tuesdays and Thursdays, but other than that (and studying) my days are free! I do also work at an organic farm in the mornings on weekends, but my afternoons and evenings are free! I’m looking to help out whenever and wherever I can. Able to wear them out with loads of play time or to just give them a good belly rub. Whatever is needed! I’m used to playing with a high energy German Shepard/Akita mix and a one year old Black Mouth Cur. Needless to say, I can hold my own against big dogs zoomies.
About: I get a lot of pleasure assisting busy professionals with their pet sitting needs. I provide a nurturing and loving environment for your special pets in a very tranquil setting. Your pets will be treated as if they were my own. My husband and I will treat your pet with the utmost care and attention. References available upon request.
About: I’ve had animals growing up all of my life including goats, horses and dogs from small to large. I have experience in both their care and for understanding their needs through hand on situations and passion. I especially love dogs because of their loyalty, love and tail wags! I’ve had my current dog from a puppy for the last year and a half and have loved seeing her grow! Your dog will always be the only dog I am watching along with mine and you can rest assure that your pup is well taken care of! I only am only available weekends with occasional changes upon request and that’s simply so that I can devote myself to being with your pet for as much of their stay as I can provide. My husband also is in the house will assist in any care needs, as he is passionate about dogs as well :) I typically take my dog on walks 3x a day or fetch sessions in the yard and can adjust scheduling as needed. My dog is friendly (very) with dogs of all shapes and sizes, is up to date on all shots and vaccinations, and has no history of violence. We are a pet friendly household that can accommodate crate training or more spoiled pups who enjoy being on the furniture as much as my Ellie does. I heavily respect rules and any needs/boundaries that you may have with caring for your pet all within good reason.
“Mark did a fantastic job with our new dog Teddy! We are long-time dog owners as is Mark, and his years of experience and bed-side manner was certainly evident and provided great peace of mind while we were away from our new pup. We will be relying on Mark in the future and strongly recommend him to others!”
About: I have always grown up surrounded by dogs of all breeds and cats as well! Personally, my family always had golden retrievers (okay, I have a soft spot). Over the years, I have always watched neighbors or family pets, including my own. I’ve helped manage any illnesses that may have come along with any dog or cat needing medications or special therapy! I have a LOT of experience with puppies and the training/ time that goes into that development as well. I also am active, so spending time and keeping the dogs and cats I watched busy and playful is super important to me. Overall, treating the pets around me like family has always been second nature to me and I hope to bring that quality to you! I will be starting a new sales role 9-5 in downtown Annapolis! With that said, my availability April 1st will move to mornings and evenings - drop ins/ walks. The remainder of March is free for all times of day! I live in an apartment that is not quite the right size for a dog of my own - however, I am excited to be taking up this opportunity through Rover as a way to still hang out with animals whether it be check ins or walking through town. Building trust is huge for me and so I hope that with future clients that is something that can be earned! I am reliable and respectful and most importantly eager to work with you 🙂
The median cost per walk for dog walking in Oakwood is $20
Dog parents share their Rover experiences - Oakwood
We can’t recommend Kayla highly enough. Throughout the last year of our elderly dog’s life, her anxiety increased as her physical capabilities and comfort decreased. Kayla was always responsible, gentle, and kind with our sweet old girl. She was also a great communicator during planning and if anything unusual came up during walks/visits (like the time we had to get her to go room to room in our house because the dog was too spooked by a recent thunderstorm to come to the door when Kayla arrived — Kayla found treats and coaxed her out from under the bed!)
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local walkers who will treat your dogs like family
1. Search
Browse profiles of walkers near you who offer dog walking
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog walking - Oakwood
Select a filter and find qualifying sitters offering dog walking.Sitters in Oakwood average 4 repeat dog walking clients
FAQs for Dog Walking - Oakwood
Frequently asked questions about Rover
As of September 2026, there are 13,092 sitters on Rover offering Dog Walking across Oakwood. 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 Oakwood. 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 Oakwood.
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 Oakwood. On Rover:
- 90% of walkers can help with special care needs
- 96% can help with giving oral medications or injections
- 96% 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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