Dog Walking Winterberry

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

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Winterberry, 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: Lauren M.
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Lauren M.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
• 7 reviews
5 repeat clients
3 years of experience
Westminster, MD, 21157

“Lauren was a pleasure to work with and having her help was greatly appreciated and our pups enjoyed her visiting ! She's very responsive and takes in feedback very well! I would recommend her to others.”

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Chris S.
Sitter Profile Image: Susan G.
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Susan G.
from
$15
per walk
13 years of experience
Westminster, MD, 21158

About: I have been pet sitting for my friends and neighbors for years, plus have had dogs of my own for 13 years. I’ve had some older dogs, and puppies. I have experience with taking care of cats and chickens as well. I’ve had 2 cats for 10 years and have 9 chickens I currently take care of! I have a flexible job that allows for me to take breaks and take care of animals throughout the day. I currently do fit in 3 training sessions for my own puppy everyday. Currently I do training with my puppy and make time as needed for other tasks. I understand being respectful in others homes and caring for animals like they are my own.

Sitter Profile Image: Lindsey W.
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Lindsey W.
from
$15
per walk
5.0 out of 5 stars
• 10 reviews
11 repeat clients
22 years of experience
Westminster, MD, 21157

“Lindsey is extremely chill and the exact perfect fit for our reactive Kevin. Kevin is excitable but as soon as he sees Lindsey he calms down and is ready for a walk. I highly recommend!!!”

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Ethan F.
Sitter Profile Image: Kelly E.
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Kelly E.
from
$25
per walk
5.0 out of 5 stars
• 62 reviews
25 repeat clients
7 years of experience
Westminster, MD, 21157

“The doggies and their owners are very happy. All questions were asked. All updates were given. Last minute request was accepted.”

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Audrey W.
Sitter Profile Image: Alexander S.
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Alexander S.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
• 13 reviews
4 repeat clients
20 years of experience
Reisterstown, MD, 21136

About: Hi there. I know how stressful it can be to find the right person to care for your pet. They’re a treasured member of your family, and you want to feel confident that they’ll be safe, comfortable, and well cared for while you’re away. I’ve been caring for animals for around 20 years. I’ve worked with pets of all sizes, personalities, and energy levels, from shy and skittish to excited, playful, and fearful. Every animal has their own unique personality, and one of my favorite parts of this job is getting to know all the little details that make your pet who they are. Their routines, habits, favorite toys, funny quirks, and what makes them feel most comfortable all matter to me. When your pet is in my care, I tailor everything to their individual needs and follow your instructions closely. I’ll care for them as if they were my own and make sure they receive the attention, affection, exercise, and companionship they need. I’ll also send plenty of photo updates, especially when your pet is being silly or cute, so you can relax and enjoy your time away knowing they’re happy and in good hands. I’m physically strong and confident handling large, powerful, and high-energy dogs, including dogs who need firm leash control, longer walks, structure, and plenty of activity. For additional peace of mind, in addition to the Rover Guarantee, I also carry my own premium Pet Care and Liability Insurance. I look forward to getting to know your pet better and becoming the best of friends. I’m available 7 days a week and have a flexible schedule throughout the day. I can help with morning, afternoon, evening, and late-night care depending on your pet’s needs. Whether you need regular visits, last-minute help, walks, drop-ins, or extended care, I’m happy to work with your schedule whenever possible. I follow each client’s instructions closely and do my best to keep every pet’s routine consistent. I know every animal has their own personality and comfort level, so I take a patient, respectful approach to care. If your pet wants playtime, attention, or companionship, I’m happy to give that. If they are shy, anxious, independent, or simply prefer space, I’m just as comfortable keeping them company from a calm and safe distance. My goal is always to help your pet feel secure, respected, and well cared for.

Sitter Profile Image: Brittany S.
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Brittany S.
Star Sitter
from
$25
per walk
4.9 out of 5 stars
• 9 reviews
2 repeat clients
28 years of experience
Hampstead, MD, 21074

About: I’ve been around animals my entire life. My childhood cat lived to 22, and I grew up with Golden Retrievers, including helping care for a litter of puppies. I also worked as an assistant manager at a large pet daycare facility and now have two rescue dogs of my own. I’m very active and love walking, so I’m happy to give dogs plenty of exercise, playtime, and attention based on their needs. Pet care fits well into my weekly routine. I work part-time in a flexible office role and can also work remotely, while I am building my real-estate career. That gives me the ability to plan my schedule around walks, drop-ins, feedings, playtime, and staying consistent with each pet’s routine. In my home, pets are treated like family. I have a fenced yard, a large back porch, a walkable neighborhood, and a park nearby for walks and playtime. My two rescue dogs are used to sharing the furniture, so visiting pets will have plenty of comfortable places to relax and feel at home. In a client’s home, I follow each pet’s routine closely—feeding, walks, playtime, medication instructions, and any house rules—while keeping you updated with photos and messages. As a former college coach and admissions counselor, I have spent most of my career in trusted, responsibility-heavy roles, and I bring that same attentiveness and care to every pet.

Sitter Profile Image: Anna S.
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Anna S.
from
$15
per walk
10 years of experience
Reisterstown, MD, 21136

About: I’ve been around dogs since the day I was born. Growing up I had a Golden & a Shih Tzu. My parents were always big dog people and passes that love onto me. One of my dogs from high school just recently had her first litter! I currently work a full time job but usually end up working nights. I love getting to help bring peace of mind to an owner and their pet as well! I don’t have a fenced in yard, but I do have plenty of leashes and treats. I have another dog myself, who is AMAZING with other pups, so they’ll never get lonely and a crate if needed!

Sitter Profile Image: Leah U.
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Leah U.
from
$10
per walk
3 years of experience
New Windsor, MD, 21776

About: I have been pet sitting for 3 years and love all animals! I have a perfect setup for animal care, including a walking trail behind my house. I’m home during the week-I have 2 middle school aged boys that are in school and my husband works long hours. I am able to get up early for morning walks or feedings. I have a fenced in yard, with stairs leading to a deck, walk out basement with kitchenette for food storage, play area, and a resting bedroom.

Sitter Profile Image: Molly R.
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Molly R.
from
$14
per walk
5 years of experience
Finksburg, MD, 21048

About: I have 2 dogs of my own and have grown up with plenty of dogs in my life and all dogs deserve to be treated perfectly and with tons of love ! I have 2 dogs currently and i’m always feeding them , walking them and snuggling with them ! I love playing with dogs and taking care of them ! Make sure they are fed, have water , let outside when needed , taken on walks , plenty of snuggles and play time ! I have dog sat for plenty of families !

Sitter Profile Image: Audrey S.
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Audrey S.
from
$35
per walk
4.9 out of 5 stars
• 119 reviews
57 repeat clients
30 years of experience
Reisterstown, MD, 21136

“Audrey was great. Super friendly, kept communication open, and most importantly, my dog loved her. Definitely will request her services again in the future.”

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Siairra
Sitter Profile Image: Corrie O.
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Corrie O.
from
$18
per walk
5.0 out of 5 stars
• 4 reviews
30 years of experience
Cockeysville, MD, 21030

About: I have had many dogs in my life time and I enjoy walking, talking to, caring for and spending time with dogs when I can. I miss my pets but I am not ready to get one of my own. However, I would love to help you care for your pet when you are gone. I am a teacher during the school year. I usually can help you out on the weekend or nights during the school year. During the summer I can help more often in a variety of days and times. My fur babies have all past. When I have helped friends and family take care of their pets I make sure to get to know their fur baby before they need me to care for them. I learn their pet's routines and I try to spend some time with them so they know my sent. This makes it more comfortable for the owner and pet when I am with them.

Sitter Profile Image: Jaime T.
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Jaime T.
from
$25
per walk
5.0 out of 5 stars
• 46 reviews
12 repeat clients
30 years of experience
Finksburg, MD, 21048

About: My daughter and I have been doing animal sitting, walking and drop ins for close family and friends over the past 5 years. As my daughter prepares for graduation in the next year, we said it’s time to make a business out of something we both love. There’s never been a time in our life that we have not had 3-4 pets of our own. From bringing home every stray dog, cat, baby bunny, possum, raccoons and birds to save and rehabilitate. We are very involved in animal rights, animal welfare, cat colony management, fostering and TNR! Even some of the most feral cats have build extremely loving relationships with us. At the moment our pets include 1 dog, 6 cats, 1 bunny and a snake. We are also very experienced with providing care for equine, rodents, parrots, chickens, ducks, sheep, goats and pigs. We volunteer at-least one day a week for an equine rescue. Along with riding and providing care for the past 11 years, we know all the ins and outs of feeding, stall cleaning, Turning in and out, plus other general equine care. We have a great relationship with numerous veterinarians in our area, including exotic, farm animal and your typical small animal veterinarians. I have experience with administering oral and injectable meds to cats, dogs and equine. We also have experience with reptile feeding. While staying at your home, Along with providing loving care to your animal(s) We can water plants, bring in mail, put garbage cans out or any other tasks you might need, so that you will be stress free when returning. Unfortunately, we can't take any more animals in at my home since we have quite a few of our own and 2 fosters at this time. ***Please make note….if you have a pet that can not stay home alone for at least 5 hours or if you have a pet that needs 24 hour care, there will be a $25 fee added to each nights stay. We love doing drop ins, dog walking and pet sitting in your house. It is our top priority to always make sure your pets are safe and loved! We are sure to always provide lots of texts and pictures to assure you that your pets are happy and loved during your time away❤️ Our drop in, walks and house sitting can be scheduled for any time of the day or week that our schedule shows an opening. We are very flexible! We can not take animals in our home at this time. All clients will stay in their own home. Your pets safety is always our top priority.

Sitter Profile Image: Candace S.
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Candace S.
from
$30
per walk
4.9 out of 5 stars
• 62 reviews
22 repeat clients
30 years of experience
Hanover, PA, 17331

“Good communication. Would highly recommend.”

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Chris A.
Sitter Profile Image: Rachel B.
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Rachel B.
from
$19
per walk
5.0 out of 5 stars
• 1 review
2 years of experience
Manchester, MD, 21102

About: I have over two years of professional kennel experience caring for dogs and cats of all breeds and personalities. I'm skilled with puppies, seniors, medication routines, and building trust with shy or anxious animals. Every pet I meet gets the same love and attention I give my own. I'm available throughout the day for walks, playtime, and companionship. Caring for animals is already part of my everyday life, so it feels completely natural to make time for your pets, too. I keep pets safe, comfortable, and cared for like they're my own. I stick to your routines, keep a close eye on details, and make sure everyone feels at ease.

Sitter Profile Image: Ambrosia H.
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Ambrosia H.
from
$25
per walk
10 years of experience
Owing Mills, MD, 21117

About: Hey there! I'm Ambrosia! You can call me Amber. I've been caring for pets for as long as I've been caring for babies. See it goes hand in hand. Every baby that I've nannied usually has a furry frind with them. The fur baby came first then the actually baby. When caring for the baby I often took a liking to the furry friend too. That meant playing and feeding the dog whenever I wasn't taking care of the baby. Often times I would let the dog out to do his buisness. When the child got older and we went on walks the dog of couse came too. As a former athlete and someone who lives an active lifestyle, I love going on walks and runs. So if your dog is a runner that's no problem for me; just let me know. Just like kids, I can understand the fustration when a pet does not listen. Being a nanny helped me to gain a lot of patience, so if your pup isn't a good listener it's ok! Ms. Amber has the time to wait it out. On the other side of that we all love a little reward so don't be shy to let me know if you have a reward system for your pet. I love dogs yound and old! As caregiver I strive to give your pet the best experience while they are in my care. I look forward to meeting and tking care of your furry friend! As I am not working a traditinal job right now, my schedule is pretty flexiable. Pet care can fit into my daily routine around your pets needs. Whether that be for an early morning walk or a a mid day pop in for cuddles and play, I can be the sitter you rely on. When caring for your fur baby in your home, I strive to keep a clean and safe enviorment for your pet and myself. Any mess that might have been made while caring for your pet will be cleaned up. I want your pet to have the best experience with me and whatever malkes them comfortable with me I'll do. I understand that we all need time to warm up to eachother. I keep a calm attitude and love to givethe equal amout of space and cuddles.

Sitter Profile Image: Alani J.
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Alani J.
from
$20
per walk
5.0 out of 5 stars
• 1 review
1 repeat client
6 years of experience
Pikesville, MD, 21208

About: I have six years of hands on experience with dogs, including volunteering at the Baltimore SPCA, where I handled intake, socialization, and daily care for dogs of all temperatures. I have also trained the dogs that I have had. I work full-time, but my schedule rotates every three weeks — so I always have afternoons free after four, plus two full days off each week. That means I’m available for midday walks, evening visits, and weekend coverage without any gaps. My dogs get a set daily rhythm in the morning and evening walks, scheduled meals, and plenty of rest so I know firsthand what a consistent routine looks like from the inside. Also I follow the owner’s routine exactly feeding times, meds, play, potty breaks and send photo updates after each visit so they always know how their pet’s doing.

Sitter Profile Image: Ember S.
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Ember S.
from
$37
per walk
5.0 out of 5 stars
• 51 reviews
11 repeat clients
6 years of experience
Owings Mills, MD, 21117

About: Family and friends have always relied on me to feed, walk, and play with their pets. Animals are my passion and it's a joy to make them happy. They need love and compassion, no matter what. I have a soft spot for senior cats and dogs, and it's a joy to provide them with comfort. I especially love working with shy cats who don't like strangers! I always get them to break out of their shell and into my lap 🥰 I put in the extra effort to make sure all animals in my care have an incredibly fun time! Nothing is more fulfilling than doting on them and providing relief for their caring owners! I have an open schedule all week, and can care for your pets any time of day, or for an extended period of time. My availability is very flexible and I'm always eager to work around everyone's schedule so your babies have the care and attention they deserve! Your pets will be safe and at ease with me. I'm respectful of their emotions and boundaries, and ensure that they know I'm only there to dote on them. Even though their parents are away, I do everything in my power to ensure they are safe, healthy, and happy.

Sitter Profile Image: Nina E.
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Nina E.
from
$25
per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
10 years of experience
Randallstown, MD, 21133

About: I love animals, especially dogs and I take pride in providing exceptional care. I am a patient, kind and supportive individual. Your dog will be happy, safe and protected with me. I am compassionate public servant with over 20 years expereience caring for pets and sitting for friends and neighbors. I believe integrity, loyalty and honesty are essential when providing care for animals. I am always available via cell phone and video chat (Google DUO) if you ever want to check-in on your pet. If a loving home is what you need for your pet while you are away, then I am the pet sitter for you. You will not be dissappointed with my services. I am more than willing and able to provide stellar references. I look forward to servicing your pet sitting needs.

Sitter Profile Image: Nicole M.
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Nicole M.
from
$16
per walk
30 years of experience
New windsor, MD, 21776

About: I've taken care of cats and dogs for the past 30 years. In the past 10 years I have enjoyed taking care of my senior Beagles and fostering! I'm off for the summer so just about any day works! In the fall, my schedule will allow Mon- Fri after 3pm. Can't wait to help out! I can help you in your home with feeding, walking and playing with your pet. If your pet just needs snuggles, I'm there for it.

Sitter Profile Image: Justin C.
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Justin C.
from
$19
per walk
5.0 out of 5 stars
• 30 reviews
8 repeat clients
14 years of experience
Hanover, PA, 17331

“Justin is great to work with! He is very communicative about our pup each day! Also appreciate the extra effort he puts in with our pup who is anxious and adjusting to our new home currently! Would absolutely recommend him!”

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Jessica L.
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The median cost per walk for dog walking in Winterberry is $20

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?

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  • 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.

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.
  3. 3. Book & Pay

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Popular requests for dog walking - Winterberry

Select a filter and find qualifying sitters offering dog walking.

Sitters in Winterberry average 4
repeat dog walking clients

FAQs for Dog Walking - Winterberry

Frequently asked questions about Rover

The average cost of Dog Walking in Winterberry is $17 per walk as of October 2026. Most bookings cost between $0 and $29 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 4,811 sitters on Rover offering Dog Walking across Winterberry. 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 Winterberry. 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 Winterberry 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 Winterberry. On Rover:

  • 88% of walkers can help with special care needs
  • 93% 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 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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