Dog Sitting in Stephenson

Book a Stephenson dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Stephenson dog sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Laura P.
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Laura P.
from
$25
per visit
31 years of experience
Winchester, VA, 22603

About: Animals have been part of my life since birth, and caring for them has always been one of the greatest joys of my life. I grew up in a home that always had dogs, and when I got my first dog in my early twenties, I continued owning and caring for dogs for nearly 31 years. While I currently share my home with three beloved cats, I’ve spent a lifetime around dogs and understand their needs, personalities, and the importance of making them feel safe, comfortable, and loved. For the past five years, I’ve also hosted guests through Airbnb and regularly cared for their pets, giving me experience with animals of all ages, sizes, and temperaments. Caring for animals isn’t just something I do—it’s something that comes from the heart. Your pet will be treated with the same love, patience, and attention that I would give my own family. I work for myself, I have a very flexible schedule and can adjust my time to meet your pet’s needs. This allows me to be available, reliable, and fully present for your pet. Whether it’s daily visits or extra attention while you’re away, I’ll make sure they are cared for, comfortable, and never feel alone. I treat every pet like my own, with safety and comfort always coming first. I live on a private five-acre property with a large, securely fenced-in yard where dogs can safely play and enjoy plenty of space. Inside, pets have a calm, clean environment with cozy spots to relax, along with toys and attention. I always supervise outdoor time and make sure every pet feels safe, comfortable, and truly cared for.

Sitter Profile Image: Samantha H.
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Samantha H.
from
$15
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Winchester, VA, 22601

About: Hello! My name is Samantha. I have grown up with all sorts of animals including dogs, cats, rats, lizards, snakes, ect. I have dog sat in the past for friends and family and have raised/helped raise several different dog breeds including a litter of 9 Doberman/cane corso puppies. I love animals and give them all the attention and care i can offer! I am not currently working, so i have a lot of free time on my hands, especially during the week to fill with animal love! I will treat your house as my own and respect your space. I will clean up any mess left from your pooch if any and follow whatever directions you leave for me

Sitter Profile Image: Alyssa F.
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Alyssa F.
from
$20
per visit
5.0 out of 5 stars
71 reviews
10 repeat clients
7 years of experience
Winchester, VA, 22601

Alyssa is so amazing with the pups, and I'm very grateful for her professionalism.

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Christian G.
Sitter Profile Image: Jacob G.
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Jacob G.
from
$20
per visit
5.0 out of 5 stars
1 review
1 repeat client
10 years of experience
Clear Brook, VA, 22624

About: With 10 years of experience caring for dogs, I'm passionate about keeping them happy and active with fun walks. I also have experience managing multiple dogs on walks. I’m currently in summer break so I have more free time than usual and I always wake up early to take my own dogs out. I always take my dogs out 3 times a day morning, evening and night. As well as giving them ample food and water in the mornings and evenings. And of course we can talk more about how I can better take care of your pup.

Sitter Profile Image: Eliza G.
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Eliza G.
from
$25
per visit
5.0 out of 5 stars
20 reviews
4 repeat clients
15 years of experience
Winchester, VA, 22602

Eliza was so good with our little Mika. Typically Mika suspicious of strangers took to Eliza quickly. Eliza was very thorough sending photos and providing updates on her time with Mika. We highly recommend Eliza!

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Belinda M.
Sitter Profile Image: Alex H.
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Alex H.
from
$18
per visit
5.0 out of 5 stars
20 reviews
9 repeat clients
10 years of experience
Winchester, VA, 22601

Alex was very professional & paid attention to detail. He was at out house when he was supposed to be and followed the directions I left for him. Next time we need someone to stop in we will definitely use him again!

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Ashleigh B.
Sitter Profile Image: Sarah J.
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Sarah J.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
78 reviews
24 repeat clients
10 years of experience
BERRYVILLE, VA, 22611

We are nervous dog parents and Sarah went above and beyond to ensure both our puppies and my husband and I were comfortable while away from them! Cannot recommend her highly enough. She is very knowledgeable and won over our most particular girl with her calm and warm presence.

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Becca K.
Sitter Profile Image: Sophia M.
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Sophia M.
from
$16
per visit
5 years of experience
Winchester, VA, 22601

About: Animals have always been a huge part of my life. I currently have 4 cats and a 4-month-old puppy, so I understand the patience, attention, and love pets need every single day. Growing up surrounded by animals taught me how to care for pets with different personalities, energy levels, and needs. From playful puppies to independent cats, I’m comfortable handling feeding schedules, walks, playtime, cleanup, and giving pets lots of affection and attention. I treat every pet like family and always make sure they feel safe, loved, and comfortable while their owners are away. I currently work a flexible part-time job, which gives me plenty of time throughout the week to care for pets and give them the attention they deserve. Since I also have 4 cats and a 4-month-old puppy of my own, pet care is already a big part of my daily routine. Caring for animals comes naturally to me, and I enjoy spending my free time with them. I make sure every pet feels safe, comfortable, and cared for whether I’m in my home or a client’s home. I pay close attention to each pet’s personality and needs, whether they’re energetic, shy, young, or older. In a client’s home, I always follow instructions carefully to keep pets on their normal routine and help them feel as stress-free and comfortable as possible while their owner is away.

Sitter Profile Image: Mya R.
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Mya R.
from
$20
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
13 years of experience
Winchester, VA, 22601

Mya is a great help and takes the best photos!

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Robert B.
Sitter Profile Image: Isabella M.
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Isabella M.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Winchester, VA, 22601

Isabella we as BEST! She communicated from the start and we were able to work out the best schedule. She sent cute pictures and videos of my girls (two cats) every time she visited and kept me up to date on their shenanigans. The girls are happy and healthy. Couldn’t have asked for a better sitter!

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Abigail B.
Sitter Profile Image: Ciera O.
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Ciera O.
from
$14
per visit
12 years of experience
Winchester, VA, 22601

About: I have 6 months of professional dog walking experience with a pet care company in Maryland, where I cared for dogs of all sizes, energy levels, and personalities. In addition, I’ve shadowed and interned at veterinary clinics, giving me experience recognizing normal pet behavior and paying close attention to each animal’s well-being. As a lifelong dog lover who owned and cared for my own dog for 11 years, I understand the importance of providing safe, reliable, and compassionate care. Whether your pup needs an energetic walk or a relaxed stroll, I’ll treat them like they’re my own and keep you updated every step of the way. I’m currently preparing for veterinary school and spend time each week shadowing veterinarians to expand my hands-on experience with animal care. This flexible schedule allows me to provide reliable weekday and weekend walks or drop-in visits while giving every pet the attention and care they deserve. My priority is making every pet feel safe, comfortable, and cared for while maintaining their normal routine. I carefully follow each owner’s instructions for feeding, walks, playtime, medications, and any special needs. I use positive reinforcement, pay close attention to behavior and body language, and ensure pets always have fresh water and a clean environment. During walks, I prioritize safety by using secure leash handling and avoiding situations that may cause stress. I also provide regular photo and text updates so owners know their pets are happy and in good hands. With my professional dog walking experience, veterinary clinic shadowing, and shelter volunteer work, I’m comfortable caring for pets with a variety of personalities and energy levels. I treat every animal with patience, compassion, and the same level of care I would give my own.

Sitter Profile Image: Sierra B.
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Sierra B.
from
$20
per visit
4.8 out of 5 stars
21 reviews
9 repeat clients
10 years of experience
Winchester, VA, 22602

Sierra is the best! She pampered and loved on my fur babies and took amazing care of them ♥️

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Sandi W.
Sitter Profile Image: Hannah H.
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Hannah H.
from
$20
per visit
5.0 out of 5 stars
13 reviews
5 repeat clients
10 years of experience
Inwood, WV, 25428

Hannah took good care of my cats, kept me up to date after every visit, was helpful, and respectful of my home. I definitely recommend Hannah as a sitter!

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Jose R.
Sitter Profile Image: Michelle B.
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Michelle B.
from
$24
per visit
5.0 out of 5 stars
35 reviews
9 repeat clients
10 years of experience
Stephenson, VA, 22656

We booked (last minute) on the recommendation of a friend who uses Barce Barks. Michelle was amazing and our doggo, who often becomes sullen when we leave, was so happy when we came home! The daily photos & videos put our kinds at ease, too. We can tell our baby was treated very well!

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Paige W.
Sitter Profile Image: Jose O.
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Jose O.
from
$15
per visit
6 years of experience
Winchester, VA, 22602

About: Hi my name is Jose Alfredo and I can be very laid back and socially outgoing with a fun and friendly personality! I love being around friendly pets and I was a previous cat owner for 4 years. I also used to share my place with my close friend and his dog of 3 years who I helped care for many times. I have other family members and friends who have pets as well and I have been around them long enough to love and know me. I have spent a lot of time around other people's dogs most of my life and have great experience with both dogs and cats. Being around other people's pets over time has given me the opportunity to know and understand different dog and cat personalities and each ones individually unique needs and traits. Book me and I will walk your dog, feed it, play with it and make sure it has gone to the bathroom. I will tend to your cats' need as well and make sure it's fed, hydrated and help maintain it's litterbox's cleaniliness and given lots of attention! I am also willing to help with small house chores like taking out the trash, bringing the bin to the front, watering your plants or any other simple house duties for no extra charge! At the moment I will go to you to take care of your pet in your home so you don't have to worry about putting your pet in a new environment it's not used to. I will make sure everything in your home is as tidy as before I even arrived. As long as you can provide me with the proper details and instructions about your pets' needs, where things are and how to get in and out of the house, then I promise you everything will be done as requested. As a way of building trust, we will arrange to do a proper meet and greet at your home or a public place like the park. This is so me and your pet can get familiar with each other, earn trust between owner and sitter, and have comfortability and assurance that your pet and home will be in good hands. Thank you for choosing me to care for your pets! I am currently flexible with availability for most days of the week as I do not have any other full time job at the moment. However, I currently am a student studying full-time and sometimes get involved in campus events, extracurriculars, and other student organizations. So Tuesdays and Thursdays I'm typically more busy with classes. But as long as the requested time works around my schedule and classes then we can make it work and I can be available whenever I am not spending time on campus. I do prefer to be notified at least 3 days in advance for requests but I am also willing to take up to same day bookings as long as I am completely free for that day, but it is not guaranteed. But please do try to reach out and book with me in advance at first if possible. I also prefer to schedule a meet and greet prior to accepting booking requests for new first time clients. But I will be more than happy to work with you so I can make a new furry friend if we are a great fit for each other! I used to play with my roommate's dog every day and feed him or take him outside to potty when the roommate was not around or unable to. I play ball with his dog, tug of war and give him belly rubs. His dog is also very attached to me as I am to him. I also was a cat owner for 4 years who I took care of every day from feeding him to ckesning his litterbox and playing with him. I hope to form this same kind of relationship with your pet!

Sitter Profile Image: Kayla O.
Verified Enhanced Background Check
Kayla O.
from
$20
per visit
5.0 out of 5 stars
11 reviews
2 repeat clients
15 years of experience
Winchester, VA, 22601

She’s Fantastic! My dog loves her! She very reliable and flexible! She was very helpful when I booked the wrong time and changed her visit time last minute!

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Lynnette C.
Sitter Profile Image: Jamie B.
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Jamie B.
from
$20
per visit
5.0 out of 5 stars
17 reviews
7 repeat clients
12 years of experience
Berryville, VA, 22611

Jamie was very good and very responsible. My two shepherds were a little difficult to handle and she found that out at our meet and greet. Instead of turning the assignment down she helped come to a solution were both her and the dogs were comfortable with the feedings. The price was reasonable and I hope she will accept future accept future requests. Thank you Jamief

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Janet K.
Sitter Profile Image: Autumn P.
Verified Background Check
Autumn P.
from
$17
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
15 years of experience
Winchester, VA, 22601

About: Hi! I’ve been an animal lover my entire life and have always had pets of my own. I worked as a kennel technician for 2 years and later as a veterinary technician for almost 2 years, where I gained hands-on experience caring for dogs and cats of all ages, temperaments, and medical needs. My background means I’m comfortable recognizing signs of stress or illness, administering basic medications, and providing calm, attentive care. While I’m no longer working in a clinic setting, the knowledge and experience I gained continue to guide how I care for every pet. I treat every animal like they’re my own — with patience, love, and close attention to their individual needs. Whether your pet loves playtime, long walks, or just quiet cuddles, I’m here to make them feel safe and happy while you’re away. I work during the week, so I primarily book weekends to give pets my full attention. When in my care, your furry friend gets walks, playtime, cuddles, and lots of love — all on a schedule that keeps them happy and comfortable. ❤️ I am available for drop ins/ walks during the week around lunch time and Fridays for boarding after 5pm! I treat every pet like family. Whether in my home or yours, they get a safe, cozy space, fresh water, walks, playtime, and plenty of love. I follow their routine and give updates so you know they’re happy and comfortable. ❤️

Sitter Profile Image: Linda S.
Verified Background Check
Linda S.
from
$25
per visit
4.9 out of 5 stars
103 reviews
53 repeat clients
40 years of experience
Clear Brook, VA, 22624

About: 5 Acres, Pool, Large PRIVATE HOME PROVIDING POOCH PAMPERING SECOND TO NONE. Dog boarding, pet taxi, walking or house sitting I do it ALL!! I have over 20 years experience with all sizes and breeds, serving Franklin, Clarke & Western Loudoun Counties in Virginia and Innwood WV. Give your baby a luxury vacation while you are away, a great day-care experience while you work or shop or I’m happy to care for your pet in their own home. Pet taxi service to/from my house, to your vet or groomer is also one of our services. Schedule a meet and greet to come see for yourself. WHY I LOVE DOG SITTING My parents raised Collie's and my first dog was Lady, I was 18 months old! So I have always had dogs, a house just isn't a home without a pup! I have owned, fostered and rescued dogs all my life. I have experience with all breeds, from Great Danes to Yorkies, I have done it! I love dogs, pamper them but give them the boundaries that make them feel secure. SERVICE AREA I am located in a large home with a pool and fenced in backyard in Clear Brook Virginia serving Winchester, Purcellville, Round Hill, Berryville, Bluemont, Hillsboro, Lovettesville and the surrounding areas. We can arrange pet taxi service to/from our home at an extra charge. CALL FOR MORE INFORMATION I’m happy to provide many references from past clients, give a phone and/or in person interview. All boarding clients must complete a meet & greet prior to booking. MEDICATION AND SPECIAL ATTENTION I am trained in administering oral medications and injections. Pet care is my full time profession, I’ve dedicated the past 20 years to watching clients pups so they can work, vacation or travel without their fur babies suffering from separation anxiety, or stress. I have unparalleled experience providing love & attention to my boarders, keeping them happy & safe overnight (or longer) while their family is away. Our pet taxi service can come pick up your baby to start their stay with us or provide excellent transport if your pup has an appointment at the vet or the spa.

Sitter Profile Image: Allison B.
Verified Enhanced Background Check
Allison B.
from
$25
per visit
5.0 out of 5 stars
16 reviews
5 repeat clients
10 years of experience
Winchester, VA, 22602

About: Hey there my name is Allison and I am a huge animal lover! I will love on your fur babies while you are gone and make sure they have what they need! As someone that has every pet but a dog of her own and has always wanted one, I will completely take advantage of the time I get with yours! I am comfortable with whatever is in need feeding, walks, backyard play, even just hanging out at the house and keeping your animal company! I have experience with a wide range of animals and I will make sure your needs are met! I am so excited and looking forward to meeting you and your sweet fur baby! Whatever animal comes my way I will make sure they are taken care of!

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Stephenson dog parents share their Rover experiences

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5.0 out of 5 stars

Myahrissa took exceptional care of my dogs, Naya and Francis, and I could not have been happier with the experience. From the moment she met them, it was clear that she genuinely loves animals and treats them as if they were her own. Throughout her time with them, she was attentive, caring, reliable, and communicative, giving me complete peace of mind while I was away. Naya and Francis absolutely adored her, and it was obvious they had an amazing time together. When I returned home, they were happy, relaxed, and well cared for—one of the best indicators that they were in great hands. I would highly recommend Myahrissa to anyone looking for a trustworthy, compassionate, and professional pet sitter. She went above and beyond, and I would not hesitate to have her care for my dogs again in the future.

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Marcus R.
Drop-In Visits
5.0 out of 5 stars

Hannah arrived just as requested, sent adorable pics, and posted what each pet was doing and how their demeanor was. It sounds like they loved her, and showed it with licks and pets!! She also brought in our mail and packages, which was very helpful! We will definitely invite her back next time!!

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Sarah P.
Drop-In Visits
5.0 out of 5 stars

Ally is always fantastic! Super communicative, great with my senior dog, and very thoughtful. Can’t recommend highly enough.

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Christiana H.
Drop-In Visits
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Dog Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Stephenson dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.

Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Stephenson.

Rover makes it easy to find Stephenson dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.