Dog Walking Winterberry

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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: Eliza W.
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Eliza W.
from
$15
per walk
5.0 out of 5 stars
• 5 reviews
4 repeat clients
4 years of experience
Finksburg, MD, 21048

“Resi loves Eliza! Eliza was very professional and on time. Took Resi on her walks at the scheduled time. We have booked with Eliza again !! Highly recommend!!”

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Megan H.
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: Madison N.
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Madison N.
from
$20
per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
6 years of experience
Westminster, MD, 21157

About: I have taken care of animals my entire life, ranging from puppies and kittens to reptiles and fish. I’m more than willing to do drop ins or even spend the night if you require. My schedule is very flexible, please reach out with and questions or concerns! During the week, I work a full-time schedule, but I’m available for visits before work, during my lunch break, and after work each evening. This makes me a great fit for morning feedings, midday potty breaks, evening walks, dinner visits, and overnight care. Weekends: I’m available with a flexible schedule and can accommodate visits throughout the day. Overnight Care: I’m available for overnight stays any day of the week, so your pets can enjoy consistent care and companionship while you’re away. I always strive to be reliable, communicative, and attentive, ensuring your pets receive the same love and care I give my own. Your pets will always be my top priority. I’ll make sure they’re well-fed, receive plenty of love, attention, and playtime, and have opportunities to relax, unwind, and enjoy lots of cuddles. I’ll also keep up with their daily care and hygiene, ensuring they’re happy, comfortable, and well cared for while you’re away. My goal is to make them feel safe, loved, and as close to their normal routine as possible.

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: Kameron B.
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Kameron B.
from
$25
per walk
10 years of experience
Westminster, MD, 21157

About: I’ve had dogs my whole life, so I’ve always been around them and know how to care for them. I’m really good with dogs and genuinely enjoy spending time with them. I’m comfortable with dogs of all different sizes and personalities, and I treat every dog like they’re my own. I’m responsible, caring, and will make sure your dog gets plenty of attention, love, and exercise while they’re with me. I work full time Monday through Friday, but I’m fully available on the weekends. During the week, I’m available for drop-ins and walks in the mornings and later in the day after work. I’ll do my best to work around your schedule and make sure your pets get the care and attention they need. I want every pet in my care to feel safe, comfortable, and loved. I’ll always make sure they are supervised and treated with patience and respect. I understand that every dog and cat is different, so I’ll take the time to learn their routine, personality, and anything they need while they’re with me. I’ll also keep you updated so you can feel comfortable knowing your pet is in good hands. My goal is to provide a calm, safe, and welcoming environment where your pet can feel right at home.

Sitter Profile Image: Olivia M.
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Olivia M.
from
$38
per walk
5.0 out of 5 stars
• 9 reviews
2 repeat clients
4 years of experience
Upperco, MD, 21155

About: I have grown up with dogs for the majority of my life. Dog breeds like pugs, Dalmatian, Australian Shepard, pitbull, boxer, doodle, blue heeler, and more! I grew up on a farm with horses, sheep cows, cats, dogs! All kinds of animals 🥰 I am very passionate about animals being taken care of the way they deserve! Along with that I have also spent 5+ years caring for snakes and other reptiles Typically I work in Sparks MD Tuesdays and Thursdays, and Shrewsbury PA most other days. My schedule varies at times and my shifts ranges anywhere from 5 hours to 8 hours don't have any pets at the moment, my townhouse doesn't allow them sadly 😔 but I have had many pets in my life ranging from cats, dogs, reptiles, hamsters, horses you name it! Pets are family and I always treat anyone's animals as such!

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: Emily N.
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Emily N.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 31 reviews
16 repeat clients
12 years of experience
Cockeysville, MD, 21030

“Emily arrived on time and was so friendly and warm greeting Sadie. She definitely provided Sadie a great walk and rewarding experience. I would definitely use Emily again?”

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Christine C.
Sitter Profile Image: Julian U.
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Julian U.
from
$30
per walk
4.9 out of 5 stars
• 113 reviews
44 repeat clients
10 years of experience
Owings Mills, MD, 21117

“Julian is amazing! I could not have asked for anyone more sensitive to the needs of our senior, special needs greyhound. He was very attentive to all details we provided, was incredibly flexible when our schedules changed, and made sure Tannin was always comfortable and happy. Tannin would even run to greet Julian when he'd come in. There's no higher praise than that!”

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Ruth C.
Sitter Profile Image: Paris K.
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Paris K.
from
$25
per walk
5.0 out of 5 stars
• 11 reviews
4 repeat clients
5 years of experience
Hampstead, MD, 21074

About: I've had a lot of dogs to watch! Every variety of sizes, ages, and breeds. With me, there will never be a dull time! I enjoy playing with them and taking walks with them. I adore getting a pup cup and taking them for vehicle rides! (Of course, if they are permitted to have it). I just want to make them happy because that's how happy they make me! I have a flexible schedule and work mostly from home. I’ll be coming to your home, so your pup gets to stay comfortable in their own environment. I’m usually around during the day, and if I ever need to step out, it’s only for a couple of hours at most. On weekends, I’m fully available and can give your pet plenty of love, walks, and attention. If you have a specific schedule or needs, just let me know in advance, I’m happy to accommodate! I make sure they stick to their normal routine so they feel comfortable and secure. I’ll come by as often as needed for walks, playtime, feeding, and any extra care your pet requires. I love spending time with them, whether that’s a walk around the neighborhood, playtime with their favorite toy, or just giving them attention and cuddles. I always keep you updated with messages and pictures so you know your furry friend is happy and cared for while you’re away.

Sitter Profile Image: Kate M.
Verified Background Check
Kate M.
from
$25
per walk
10 years of experience
Parkton, MD, 21120

“Kate and my dog got along great. I was nervous because he had a tummy problem the day before, but she followed the request I sent her the night before/note I left at the house and my dog had a stress free day in his own house while I took a day trip to visit family. Would definitely use her again!”

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Arianne B.
Sitter Profile Image: Ryan H.
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Ryan H.
from
$25
per walk
5.0 out of 5 stars
• 262 reviews
47 repeat clients
22 years of experience
Owings Mills, MD, 21117

“Ryan was so attentive and went above and beyond for our leash-reactive pup on their twice-daily walks. He made us feel comfortable leaving the country and leaving our dog in someone else’s care.”

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Lisa D.
Sitter Profile Image: Andrea M.
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Andrea M.
from
$15
per walk
5.0 out of 5 stars
• 3 reviews
2 repeat clients
5 years of experience
Hanover, PA, 17331

About: Hello! I’m Mags (Rover requires me to use my legal name) and I love all animals I have been passionate about dogs ever since I was a child but because experienced working with dogs and cats (and some bunnies) while working for the Humane Society of Memphis and Shelby County. I was a veterinarian assistant for one year and then became an adoptions Manager for three years. This was the most fulfilling experience of my adult life, being able to help animals and the community daily. I recently lost my closest companion, Xander, about a month ago. He was 13 years old and I had him since he walked into the humane society at two months old. Through him I gained even more experience with aging dogs, medical care and many behavioral changes as he aged. While using positive reinforcement training we navigated 6 military moves, life adaptions to aging and the introduction of two kittens. I will take all this experience and use it to provide the same amount of love an attention for you furry family members as I did for Xander. I am currently employed part time and have many days free as well as can stay over night or board animals in my home. I have a very flexible schedule and am happy to work with any client’s schedule as needed. I currently only have two cats in my home, so I’m able to provide boarding for cat friendly animals. I have a fenced in back yard and am usually not gone from the house for more than four hours. I also am available for staying over nights at clients houses for a more comfortable experience for everyone in the family.

Sitter Profile Image: Alyssa P.
Verified Enhanced Background Check
Alyssa P.
from
$25
per walk
5.0 out of 5 stars
• 8 reviews
2 repeat clients
13 years of experience
Parkton, MD, 21120

“You are awesome!! Thank you for taking such good care of my little boy. The way you tuned in to Nash is so appreciated. He is crazy about you!!!”

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Jen W.
Sitter Profile Image: Lane M.
Verified Enhanced Background Check
Lane M.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
8 years of experience
Glenville, PA, 17329

About: I have several years of experience caring for a wide variety of animals. I am currently pursuing my education to become a Small and Large Animal Veterinarian and specialize in Animal Psychology and Internal Medicine/Oncology. Through my experience, I have developed strong knowledge and skills in pet training, dog walking, proper nutrition and feeding, and medication administration. Pet care fits naturally into my daily and weekly routine. I currently work a part-time job on Mondays, Wednesdays, and every other Saturday from 2:30 PM to 8:30 PM, which allows me to maintain a flexible schedule for my pet care clients. I keep my Rover calendar up to date to accurately reflect my availability, though occasional changes may arise. If you don't see the dates or times you need, I encourage you to reach out anyway—I’ll always do my best to accommodate your schedule and provide exceptional care for your furry family member! I do not offer in-home boarding, but I am happy to provide care in your home. I strive to maintain your pet’s normal routine to keep them comfortable and stress-free. When possible, I am available for extended stays, which can provide added consistency for your pet’s care and fit well with my schedule. I also recommend that clients leave detailed care instructions, as every pet has unique needs, routines, and preferences.

Sitter Profile Image: Annie M.
Verified Enhanced Background Check
Annie M.
from
$25
per walk
5.0 out of 5 stars
• 6 reviews
10 repeat clients
20 years of experience
Lutherville, MD, 21093

“So reliable and so responsive! Thank you, Annie!”

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Fei K.
Sitter Profile Image: Areli S.
Verified Enhanced Background Check
Areli S.
from
$27
per walk
4.6 out of 5 stars
• 7 reviews
2 repeat clients
6 years of experience
Reisterstown, MD, 21136

“We had Areli housesit and loved her so much we booked her as a regular dog sitter! She is timely, communicative and our pets love her ☺️”

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Kristin W.
Sitter Profile Image: Ember S.
Verified Enhanced Background Check
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: Justin C.
Verified Enhanced Background Check
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?

  • Cashless payments

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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

    It's that easy! All payments are processed through Rover's secured platform.

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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