Dog Walking Woods Landing

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

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Over 87
pet parents in Woods Landing have booked dog walking

Woods Landing, 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: Elena K.
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Elena K.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
• 21 reviews
5 repeat clients
10 years of experience
Annapolis, MD, 21409

“Elena helped us walk our dog(Blue) when we were visiting Annapolis. She can be 100% trusted and dependable. We didn’t even get a chance to meet Elena. But she took care of the walk as if she has known Blue for years. Thanks again!”

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Subbiah S.
Sitter Profile Image: debi t.
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debi t.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
• 112 reviews
35 repeat clients
30 years of experience
Annapolis, MD, 21409

“Debi exceeded my expectations. She communicated thoroughly and provided photos. She was definitely thinking about what was best for our pets as well as us. I hope to get to have her spend time with our pets again and again. I know I can fully trust her.”

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Donna M.
Sitter Profile Image: Allison G.
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Allison G.
from
$15
per walk
5.0 out of 5 stars
• 68 reviews
34 repeat clients
20 years of experience
Annapolis, MD, 21409

“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.”

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Natalie E.
Sitter Profile Image: Alexia M.
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Alexia M.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
• 48 reviews
16 repeat clients
10 years of experience
Annapolis, MD, 21409

“We absolutely love, Alexia! She is consistently punctual and genuinely engages with our dog during his walks. What really stands out as how well she manages him, especially when he gets reactive around cars and certain dogs. Alexia took the time to do a meet and greet before our first walk, which made all the difference in ensuring everything went smoothly. We've already booked her for multiple walks and will definitely continue using her services. We feel so fortunate to have found her!”

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Nathaniel V.
Sitter Profile Image: Ryan L.
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Ryan L.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
• 14 reviews
4 repeat clients
25 years of experience
Annapolis, MD, 21409

“Highly recommend Ryan! He took the time to do a meet and greet and really understand my dog’s specific needs. He was very communicative and flexible whenever any changes came up, which I truly appreciated. What stood out most was how he followed my dog’s training routines and even used the exact phrases we’ve been working on. He handled my dog’s reactivity with care and confidence, and it made a huge difference. I felt completely at ease knowing my dog was in such good hands!”

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Stacie Z.
Sitter Profile Image: Alexandra M.
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Alexandra M.
from
$32
per walk
4.6 out of 5 stars
• 10 reviews
4 repeat clients
8 years of experience
Annapolis, MD, 21409

“So nice and living toward our dog, Captain.”

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Kathleen M.
Sitter Profile Image: Alexxis E.
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Alexxis E.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 33 reviews
9 repeat clients
15 years of experience
Annapolis, MD, 21409

“Extremely helpful and flexible with scheduling times. Managed two Siberian huskies with no issue on long walks. Definitely recommend and will use again!”

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Keith K.
Sitter Profile Image: Gabby M.
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Gabby M.
from
$15
per walk
5.0 out of 5 stars
• 2 reviews
15 years of experience
Annapolis, MD, 21409

“Gabby was great! She was reliable, communicative, and took great care of my dog! I really appreciated her help and would definitely book with her again!”

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Elle M.
Sitter Profile Image: Owen K.
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Owen K.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
• 62 reviews
12 repeat clients
10 years of experience
Severna Park, MD, 21146

“Owen is reliable, kind and trustworthy. He shows up, gives my dog a good walk regardless of the weather, and responds quickly. I highly recommend him to anyone that needs a walker.”

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James T.
Sitter Profile Image: Leah B.
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Leah B.
from
$20
per walk
5.0 out of 5 stars
• 3 reviews
2 repeat clients
4 years of experience
Arnold, MD, 21012

About: I have been around animals my entire life! Growing up my family had dogs, chickens, cats. Currently we have 2 beagles and a black cat named Izzy! My other family members began asking me to watch their animals when they went away on trips or to stop by the house if they were stuck at work. This branched to them recommending me to their friends and now here we are! I have been watching the furry loved ones of others for about 4-5 years now and have loved every second of it. I know how scary it can be to leave behind the animals that you consider your children so I am here to make that process a little easier! I’ve taken care of puppies, dogs, cats, chickens, sheep, and horses. All animals deserved to be spoiled and loved by all 💛 I am currently a therapist that works mostly afternoon/evening hours. My daytime availability ranges day to day but getting to create my own schedule allows for flexibility! Owners know their pets best! Any information provided to me about your furry friend will be implemented so that all parties feel safe and well cared for!

Sitter Profile Image: Juliette F.
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Juliette F.
from
$20
per walk
5.0 out of 5 stars
• 7 reviews
2 repeat clients
10 years of experience
Annapolis, MD, 21401

About: I've taken care of neighborhood cats/dogs for over 10 years. I grew up taking care of both cats and dogs in my own home as well. I am comfortable walking, feeding, and cleaning up after pets. I have also volunteered at various animal shelters throughout the years. I am a graduate school student, so I am currently only accepting requests for Friday evenings, and all day on Saturdays and Sundays. I currently have a flexible schedule during the summer months and am available most weekends and weekdays. I work on Thursdays and Fridays, but I am available to care for your pet in the evenings on these particular days. I would love to connect with you to find a schedule that works best for you and your pet! I have experience walking, feeding, crating, and cleaning up after pets in the home. I'm not currently looking to house pets in my own home!

Sitter Profile Image: Ryan B.
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Ryan B.
from
$23
per walk
5.0 out of 5 stars
• 8 reviews
8 years of experience
Annapolis, MD, 21409

About: Hi everyone! My name is Ryan, and I’m beyond excited to walk/hang with your pets! I take this job very seriously, as I’ve grown up with dogs and cats my whole life and have experience walking/sitting for many different pets (of all sizes/breeds/and temperaments). Send me a message with any requests! I work part time and do freelance so I have a lot of availability to take care of your pet’s needs, whether that be some extra attention, playtime, walks, drop-ins etc. Just shoot me a message and I can more than likely make myself available for whatever your needs may be! I am very respectful when entering clients homes to take care of their pets. I myself have grown up with dogs and cats, and completely understand all boundaries pet parents may have - whether they’re allowed on the furniture, outside, crate-time etc. The rules and routine you've established with your pets is what's most important! Whether you have a shy cat that just needs to be fed, or a rambunctious dog that needs to get its energy out, I've got you covered!

Sitter Profile Image: Lisa H.
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Lisa H.
from
$15
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
5 years of experience
Arnold, MD, 21012

About: I've been taking care of family and friends dogs for over 5 years. And used to have dogs and cats of my own. I have many fur-nieces and fur-nephews and love them as my own. Because I work remotely, I can take my work anywhere. So, I will be able to stay with your pet for the duration you are gone. I work from home. And have the ability to work from anywhere. I will bring my laptop and be able to work and keep your baby company. Taking care of them in familiar surroundings.

Sitter Profile Image: Lee M.
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Lee M.
from
$30
per walk
5.0 out of 5 stars
• 11 reviews
3 repeat clients
8 years of experience
Annapolis, MD, 21409

About: I've lived with dogs just about my entire life, and I've assisted in their care from the beginning to end of their lives. I currently live with one dog in the house, and I care for him alone on weekdays, including administering medications when needed. I also have experience taking care of other types of animals - I am versatile and flexible. I care for my own pet during the weekdays, but for most of the week he uses a daycare service, leaving me free to spend longer amounts of time elsewhere. He is also older and okay with being left in the house for a few hours even when I'm the only one watching him. I'm more than comfortable watching the house as well as the pets, and I will make sure that any house rules (no paws on the counter, etc) are upheld. As long as I'm acquainted with your house facilities, I will leave the place as neat as when I arrived, if not a little cleaner. :)

Sitter Profile Image: Harrison S.
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Harrison S.
from
$16
per walk
5.0 out of 5 stars
• 17 reviews
3 repeat clients
4 years of experience
Annapolis, MD, 21403

“Harrison is always on time and keeps me up to date on how my pet is doing! I know I can count on him!”

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Aarti C.
Sitter Profile Image: Abby D.
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Abby D.
from
$15
per walk
6 years of experience
Arnold, MD, 21012

About: I have experience caring for dogs of all sizes and ages, from small dogs to large breeds and playful puppies. I’m currently training our own puppy, so I have hands-on experience with patience, consistency, basic training, and keeping a young dog engaged. I understand that every dog has their own personality, routine, and needs, and I’ll take the time to make sure your pet feels comfortable, loved, and well cared for. I work three days a week, which gives me a flexible schedule and plenty of availability on my days off, especially weekends. I enjoy spending time with pets and can dedicate time to walks, playtime, training, and companionship. My flexible schedule allows me to give each pet the attention they need rather than simply fitting them into a busy routine. I want every pet in my care to feel safe, comfortable, and at home. We have a backyard (not fenced) and are close to great walking paths, a golf course, and a dog park, so there are plenty of opportunities for walks, play, and exercise. I’ll follow your pet’s normal routine as closely as possible and adjust activities based on their age, energy level, and personality. Most importantly, they’ll get plenty of attention, affection, and supervision while you’re away.

Sitter Profile Image: James C.
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James C.
from
$25
per walk
5.0 out of 5 stars
• 7 reviews
16 years of experience
Arnold, MD, 21012

About: Pet Care Experience & What Sets Me Apart I have a lifetime of hands-on experience as a pet owner and caregiver. My two white Pitt-mixes, ages 9 and 7, have given me a deep understanding of raising dogs from puppyhood through their senior years. I'm set apart by my ability to connect with animals of all temperaments. I have a solid grasp of dog behavior, honed by training one of my own dogs and patiently working with another to overcome social anxieties. This experience allows me to build trust and confidently manage a wide variety of personalities. For over 17 years, I've provided both short and long-term care for numerous German Shepherd mixes, so I'm comfortable with large, high-energy breeds. More recently, I regularly helped a friend with their foster dogs, acting as a dog walker, playmate, and emergency contact. I'm also reliable with cats and have routinely cared for my neighbor's cat, including feeding, refreshing water, and daily litter box scooping. I offer a professional and consistent approach to pet care. My goal is to provide a stress-free experience for both you and your pet by ensuring their specific needs are met with attention and care. Weekends I am flexible enough to assist with pet care. Likewise, on Wednesdays I WFH, which allows me some flexibility to help with mid-day walks and bathroom breaks. When I come to your home, I'll always provide your pets and your space with the utmost care and respect. I will always match their energy: if they want to play, we'll play; if they want to snuggle, we'll snuggle; if they need space, I'll be sad, but I'll completely understand.

Sitter Profile Image: Tiffany O.
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Tiffany O.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
30 years of experience
Annapolis, MD, 21409

About: I am a true animal lover. I think animals become our family and I want you to feel comfortable that I will treat your pet like my own went in my care. I have experience with many kinds of animals, dogs, cats, hamsters, and reptiles. I am patient and kind and love to get to know your pet. This is currently my only job, so my schedule is very flexible. I am available morning, afternoons and evenings for visits. I can help on weekdays or weekends. I first get to know your pets basic needs, ensuring their safety, and offering enrichment. This includes feeding, providing fresh water, ensuring proper elimination, creating a safe and comfortable environment, offering exercise and playtime, and attending to any medical or behavioral needs. I am comfortable with small and large dogs as well as small pets and reptiles.

Sitter Profile Image: Adrienne A.
Verified Background Check
Adrienne A.
from
$20
per walk
5.0 out of 5 stars
• 5 reviews
4 repeat clients
20 years of experience
Annapolis, MD, 21403

“Adrienne is very reliable and punctual and Cannon enjoys his daily walks with her.”

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Sadie S.
Sitter Profile Image: Debra P.
Verified Enhanced Background Check
Debra P.
from
$20
per walk
50 years of experience
Arnold, MD, 21012

About: Ive taken care of my personal and family pets since i was 6 years old. Over these many years, other friends/ family have entrusted me with the care of their furry, feathery, and swimming family members. I have taken care of youngsters to older pets. From dogs, to chickens... I have you covered. I prefer to stay at your house. It keeps your loved one in their familiar environment. The care and safety of your pets( and your house) is my highest concern. I will become you pets second favorite human, after you. I currently work a very set schedule for work but am able to adjust it to my clients needs. My reliability and flexibility makes me an ideal caregiver. I prefer to keep your family member/s in their own environment. It helps to make them feel safe and comfortable. Each client is given my full attention especially to keep their routine and follow any instructions that is special to each of my clients. And always keeping your loved ones happy, healthy, and safe.

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

Dog parents share their Rover experiences - Woods Landing

1 / 1
5.0 out of 5 stars

We have used Debi several times to take care of our young black lab and cat. She’s great! Very responsive and loving towards the animals.

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Alexa W.
Dog Walking
5.0 out of 5 stars

Amber has great energy and was so caring with my pup! I had complicated instructions each visit and Amber was understanding and happy to make sure everything went safely and smoothly. Definitely will book in the future!

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Caitlin I.
Dog Walking
5.0 out of 5 stars

Gabby was great! She was reliable, communicative, and took great care of my dog! I really appreciated her help and would definitely book with her again!

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Elle M.
Dog Walking
5.0 out of 5 stars

Elena helped us walk our dog(Blue) when we were visiting Annapolis. She can be 100% trusted and dependable. We didn’t even get a chance to meet Elena. But she took care of the walk as if she has known Blue for years. Thanks again!

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Subbiah S.
Dog Walking
5.0 out of 5 stars

Cheri is the best! Super communicative and reliable, our dog is not easy but she knows how to take great care of him.

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Carley C.
Dog Walking
5.0 out of 5 stars

Highly recommend Ryan! He took the time to do a meet and greet and really understand my dog’s specific needs. He was very communicative and flexible whenever any changes came up, which I truly appreciated. What stood out most was how he followed my dog’s training routines and even used the exact phrases we’ve been working on. He handled my dog’s reactivity with care and confidence, and it made a huge difference. I felt completely at ease knowing my dog was in such good hands!

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Stacie Z.
Dog Walking
5.0 out of 5 stars

Captain is a bark greeter and Alexia did a great job at keep calm and welcoming his excitement. He seemed very happy after the walk and hung around her a bit before she left. Overall fantastic experience.

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Jessica G.
Dog Walking
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Meet local walkers who will treat your dogs like family

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Popular requests for dog walking - Woods Landing

Select a filter and find qualifying sitters offering dog walking.

Sitters in Woods Landing average 4
repeat dog walking clients

FAQs for Dog Walking - Woods Landing

Frequently asked questions about Rover

The average cost for Dog Walking in Woods Landing on Rover is $21.4 per walk (as of September 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 September 2026, there are 10,788 sitters on Rover offering Dog Walking across Woods 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 Woods 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 Woods 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 Woods Landing. On Rover:

  • 91% of walkers can help with special care needs
  • 97% 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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