Dog Walking Winfield

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

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Over 2
pet parents in Winfield have booked dog walking

Winfield, 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: Liz A.
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Liz A.
from
$32
per walk
5.0 out of 5 stars
96 reviews
20 repeat clients
20 years of experience
Sykesville, MD, 21784

Liz was attentive, caring and punctual. She has a love of dogs and it shows in her interactions. She took the time to walk my dog as well as make sure he was settled in before she left. We would definitely use her again!

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Sarah G.
Sitter Profile Image: Leslie R.
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Leslie R.
Star Sitter
from
$20
per walk
4.8 out of 5 stars
22 reviews
9 repeat clients
5 years of experience
Mount airy, MD, 21771

Thank you so much for walking Abby and navigating the door situation.

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Taylor S.
Sitter Profile Image: Jonathan & Jen H.
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Jonathan & Jen H.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
94 reviews
31 repeat clients
43 years of experience
Westminster, MD, 21157

Jen and Jonathan walked our dog Little Belle twice a day for over an hour each time. Our dog loved them and couldn’t stop wiggling her tail whenever they arrived. They were super reliable and helpful and made this a great experience for all of us. We will definitely book them again!

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Kay R.
Sitter Profile Image: Lin M.
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Lin M.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
61 reviews
17 repeat clients
30 years of experience
Woodbine, MD, 21797

Just in the few walks we've scheduled with Lin, I can already tell she's the best dog walker we've ever had. Our dog looks forward to their walks together! I've also noticed how much better our dog walks on leash with us - she's not pulling as much.

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Sandra W.
Sitter Profile Image: Ryan H.
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Ryan H.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
249 reviews
47 repeat clients
22 years of experience
Owings Mills, MD, 21117

I am so glad to have found Ryan. Snoopy , aside from looking back at me, went willingly on his walk. If I can’t take my Snoopy for a walk now I know

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Ellen F.
Sitter Profile Image: Tracie L.
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Tracie L.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
8 reviews
8 repeat clients
13 years of experience
Owings Mills, MD, 21117

Tracie is amazing. She has saved the day for me a few times already with last minute walks. She is wonderful with my dogs and always takes lots of pictures and gives them lots of love and attention!

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Rebecca F.
Sitter Profile Image: Kristen M.
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Kristen M.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
61 reviews
19 repeat clients
11 years of experience
Sykesville, MD, 21784

Kristen took wonderful care of our dog, Chica, on August 1. She visited our home three times throughout the day and kept us updated after each visit with detailed notes and plenty of photos, which gave us great peace of mind while we were away. Communication was excellent from start to finish, and it was clear that Chica was comfortable with her and enjoyed spending time with her. We were very happy with the care and attention Kristen provided and truly appreciated her professionalism and reliability. We wouldn't hesitate to book Kristen again in the future and highly recommend her to anyone looking for a caring and dependable pet sitter!

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Rocio C.
Sitter Profile Image: Destiny R.
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Destiny R.
Star Sitter
from
$23
per walk
4.9 out of 5 stars
106 reviews
45 repeat clients
8 years of experience
Ellicott City, MD, 21042

This is our first experience using a dog walker with Rover and we are very pleased with Destiny! We needed someone to walk our dog 3 times a day for two days. She arrived on time for all 6 walks and sent pictures of each walk. We will definitely use her again in the future!

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Kathleen R.
Sitter Profile Image: Kelly E.
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Kelly E.
from
$25
per walk
5.0 out of 5 stars
59 reviews
23 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: Lauren M.
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Lauren M.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
5 reviews
4 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: Brooke S.
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Brooke S.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
24 reviews
8 repeat clients
3 years of experience
Mount Airy, MD, 21771

Trustworthy, kind, loves my puppy. Highly recommend!

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Heather M.
Sitter Profile Image: Hannah H.
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Hannah H.
from
$20
per walk
5.0 out of 5 stars
1 review
4 years of experience
Sykesville, MD, 21784

About: I’ve taken care of my neighbors dogs for as long as I can remember. I also have a loving dog of my own therefore making me a great sitter for you and your pets! I have also been pet sitting through facebook this summer which has given me lots of experience. :) I’m a rising sophomore at JMU and am home for the summer looking for any pet sitting jobs! I have an extremely flexible schedule and can work weekdays as well as weekends. I would feed them, play with them, make sure they stay out of trouble, and occasionally reward them with treats! I would also take them outside to use the bathroom frequently as well as long walks or playing :)

Sitter Profile Image: Layla K.
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Layla K.
from
$30
per walk
5.0 out of 5 stars
9 reviews
1 repeat client
5 years of experience
woodbine, MD, 21797

About: I have always had dogs and cats growing up, which peaked my interest in animal care. In high school I worked as a kennel technician at a boarding kennel and gained an internship at the local veterinary office. now in college, I am studying animal science to hopefully get a degree in veterinary medicine, and continue to pet sit for my friends and family including both cats and dogs. I'm currently home from college for the summer, and home most of the time! I do have a car, and am available almost any time of the day. I have pets in my home that are not socialized, so I would not be able to pet sit in my own home, but I am happy to make the trip to the comfort of their own home.

Sitter Profile Image: Wydia T.
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Wydia T.
Star Sitter
from
$38
per walk
5.0 out of 5 stars
201 reviews
78 repeat clients
16 years of experience
Columbia, MD, 21044

Wydia did 3 walks a day with my Akita. Not one issue!!! Let's add she texted Grandma each time prior to coming!! When she came to met Grandma, Kiato ran to her!! That made heart smile!! She loves her job and is a lovely person!

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Angelina W.
Sitter Profile Image: Bronte B.
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Bronte B.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
197 reviews
57 repeat clients
15 years of experience
Pikesville, MD, 21208

Bronte is awesome with my pup! When she takes photos or videos, I can tell my dog enjoys her visits and walks! In addition, my stay at home neighbor made a comment about how awesome she was w my dog…,Having fun w her and playing!

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Shelly L.
Sitter Profile Image: Kenneth P.
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Kenneth P.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
250 reviews
73 repeat clients
24 years of experience
Germantown, MD, 20874

Ken has walked our 2 Labs Art and Nola a few times now. He is always dependable and great about posting pictures and report card for both pups. We highly recommend him to walk your fur babies!

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Janet H.
Sitter Profile Image: Katharine D.
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Katharine D.
from
$25
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
13 years of experience
Sykesville, MD, 21784

About: I’ve been caring for pets since I was 5 years old and have grown up with both bunnies, cats and dogs of all sizes, giving me over 13 years of hands on experience. Throughout the years, I’ve helped with feeding, walking, playtime, grooming, cleaning up after pets, and making sure they feel safe, happy, and comfortable. I understand that every pet has its own personality and routine, so I’m committed to following your instructions and providing patient, dependable, and loving care. Whether it’s going for walks, sticking to a feeding schedule, or simply giving your pet companionship while you’re away, I’ll treat them with the same love, attention, and respect that I give my own pets. I am currently working part time so I am available early morning and afternoons up until 3/4/5pm during the weekdays and weekends. Pet care has been a part of my daily life since I was a child. I currently care for my own cats every day by feeding them, cleaning their litter boxes, playing with them, and making sure they’re happy and comfortable. I also have experience caring for dogs, including walks, exercise, feeding, and companionship. I work part-time in the evenings, which leaves my mornings and afternoons available for pet care. When house sitting, I’ll make sure your pet’s routine is followed closely and that they receive plenty of attention, exercise, and affection while you’re away. I believe every pet deserves to feel safe, comfortable, and loved while their owner is away. I take the time to learn each pet’s routine and follow all care instructions closely, including feeding schedules, walks, medications (if needed and instructed), playtime, and any special requests. I prioritize your pet’s safety by keeping a close eye on them during walks and outdoor time, making sure doors, gates, and leashes are secure. I also understand the importance of respecting your home, keeping it clean, and providing regular updates with photos and messages so you can have peace of mind while you’re away. My goal is to make your pet feel happy and cared for in the environment they’re most comfortable in their own home.

Sitter Profile Image: Evie I.
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Evie I.
from
$50
per walk
5.0 out of 5 stars
34 reviews
14 repeat clients
20 years of experience
Silver Spring, MD, 20906

Evie walked both the boys for the holiday and I am so appreciative! They both got a good break while we were out for the evening. Definitely would book again!

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Codie H.
Sitter Profile Image: Tierra H.
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Tierra H.
from
$15
per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
10 years of experience
Owings Mills, MD, 21117

Tierra is amazing with Kodi! Reliable, caring, and always professional. Kodi loves his walks with her, and I love knowing he’s in great hands. Highly recommend!

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Carol H.
Sitter Profile Image: Leilani & Jessie M.
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Leilani & Jessie M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
134 reviews
39 repeat clients
20 years of experience
Hanover, PA, 17331

Leilani has quickly become a favorite of ours and clearly our dog, Doc adores her! She’s a great communicator and gets back with us very promptly when we request her help.

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Jan H.
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The median cost per walk for dog walking in Winfield 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

    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. 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 - Winfield

Select a filter and find qualifying sitters offering dog walking.

Sitters in Winfield average 4
repeat dog walking clients

FAQs for Dog Walking - Winfield

Frequently asked questions about Rover

As of August 2026, there are 12,226 sitters on Rover offering Dog Walking across Winfield. 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 Winfield. 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 Winfield.

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 Winfield. 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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