Dog Walking Winchester

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Over 137
pet parents in Winchester have booked dog walking

Winchester, 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: Kimberly B.
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Kimberly B.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
325 reviews
115 repeat clients
8 years of experience
Winchester, VA, 22601

We’ve hired Kim a few times to feed and walk our dog. She is very reliable and friendly and takes great care of our dog. The Winchester community is lucky to have someone like Kim to look after our pets :)

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Robert F.
Sitter Profile Image: Hannah D.
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Hannah D.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
85 reviews
21 repeat clients
10 years of experience
Winchester, VA, 22602

⭐️⭐️⭐️⭐️⭐️ A True Gem – Like Family to Us and Maximus! We feel incredibly lucky to have found Hannah—she’s not just a dog walker, she’s part of our family. Our dog Maximus is truly our baby (especially now that our kids are grown and out of the house), and knowing that Hannah cares for him with the same love and attention we do means the world to us. Hannah has been with us for over three months now, and in that time she’s become someone we fully trust with our most spoiled and beloved family member. She’s reliable, flexible with our crazy schedule, and always greets Maximus with affection and warmth. You can tell she genuinely loves what she does. Maximus absolutely adores her! She goes above and beyond to make sure he feels cared for when we’re not home, which gives us such peace of mind. We treasure Hannah and everything she does for our family. If you’re looking for someone who will love your dog like their own, look no further. She’s truly one of a kind.

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Gigi F.
Sitter Profile Image: Charissa L.
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Charissa L.
from
$17
per walk
5.0 out of 5 stars
14 reviews
4 repeat clients
15 years of experience
Winchester, VA, 22601

Charissa has been great to work with! Glad we found her.

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Ellen D.
Sitter Profile Image: Lisette R.
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Lisette R.
from
$15
per walk
5.0 out of 5 stars
79 reviews
32 repeat clients
6 years of experience
Winchester, VA, 22601

Lisette is great with my dogs! We have an older dog that she comes and walks and he loves it. We also just got a puppy and she has been coming over in the middle of the day to take him and our older dog on small walks and it’s been great!

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Kylie J.
Sitter Profile Image: Suellen W.
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Suellen W.
from
$18
per walk
2 years of experience
Winchester, VA, 22601

About: I’ve had dogs my entire life, and got into dog training 2 years ago. I assisted a dog training company with the dogs they would board and care for, and assisted with multiple training outings. I also raised and trained my own service animal. I’m currently working part time, and will focus solely on providing care for your pet and home. They are my number one priority and love to do things with them. I will take them on long walks and do training with them to get their brain going. I’ll make sure their meals are extra tasty and made with love.

Sitter Profile Image: Drew B.
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Drew B.
from
$15
per walk
8 years of experience
Winchester, VA, 22603

About: Everyone calls me when they need a reliable and dedicated pair of hands to watch over their children. Yes, I treat every dog like a furry child. I've helped raise dogs from 6 weeks to 16 years old. The young and the old need a little more attention and I'm happy to help. Those terrible 2's just need extra attention, and I'm happy to provide that too! I love all animals and will probably treat the kids like royalty. I prefer the company of dogs than my friends, they could vouch for that! I'm both loving and also stern because I've raised both labs and pitties. They require different types of parenting techniques, and I am equipped to handle anything. I work full time, Monday through Friday, 9 to 5. I'm happy to use my work breaks to check on animals for those who need the extra attention. My availability will be based around my work and my 2 kiddos at home. I can adjust weekly routines to incorporate pickup/drop offs, stop in visits, after work walks, or overnight stays. I treat dogs like they are our kids. I talk to them, I cuddle with them, and I use positive reinforcement to train good habits. I've helped raise a dozen dogs and each dog likes to show you how they like to be treated. I learned this lesson the hard way when I was raising dogs and had to learn different techniques to train each of them individually. Labs learn and function much different than bulldogs and pitbulls. I treat each dog the same regardless of size or attitude. Though I may give them some attitude when mouth off, like I do with my pitty at home (lol). I'm a safety first kind of person when it comes to our kids. So I tend to lean on the side of caution and extra equipment when interacting with most dogs. I always keep extra dogs supplies in my truck at all times as I have been known to that guy who stops traffic to try to rescue a dog. I've done this probably 6 or 7 times.

Sitter Profile Image: courtney b.
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courtney b.
from
$17
per walk
5.0 out of 5 stars
49 reviews
14 repeat clients
20 years of experience
Winchester, VA, 22601

She was fantastic. Both my boys like her I would recommend her to anyone with any size dog.

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Brian H.
Sitter Profile Image: Autumn G.
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Autumn G.
from
$15
per walk
12 years of experience
Winchester, VA, 22601

About: I have been around dogs majority of my life from puppy to senior. I have two dogs medium to larger dogs at home and have watched smaller dogs overtime. I am currently a college student athlete with free time during the day and night. I am very flexible with my schedule and pretty open on the weekends. I tend to be home from classes around 2-3:30pm. At home, my dogs are on shock collars because we have an open backyard that backs up to the woods. But I have also took care of several dogs that had fenced in backyards where they can freely roam.

Sitter Profile Image: Alexsys T.
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Alexsys T.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
310 reviews
119 repeat clients
7 years of experience
Clear Brook, VA, 22624

Alexsys is awesome. Communicative, thorough, and sends me all the updates and photos I need when I’m away. She even sent a picture of my porch kitty!

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Jenelle B.
Sitter Profile Image: Hailey C.
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Hailey C.
from
$21
per walk
10 years of experience
Winchester, VA, 22602

About: I have been a pet owner for as long as I can remember. I have had both dogs and cats and love them both equally. I have cared for pets for both family members and friends. I've watched all types of animals with many different personalities. On top of pet sitting, I have fostered multiple litters of kittens, which has taught me patience and attentiveness. In my free time, I also enjoy volunteering at a local rescue to help walk dogs. I understand the hard work, attention and love that goes into managing any kind of animal, and I am willing to do just about anything to make sure that your pet feels loved and safe. I am a grad student who only has in person classes on Tuesday typically 8am - 4pm, which makes me very flexible for the rest of the week. I am very conscious about safety when it comes to walk, and/or letting dogs out in a fenced in area. I am sure to read any instructions before hand to learn about any issues individual pet needs.

Sitter Profile Image: Autumn P.
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Autumn P.
from
$17
per walk
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: Kayla O.
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Kayla O.
from
$20
per walk
5.0 out of 5 stars
11 reviews
2 repeat clients
15 years of experience
Winchester, VA, 22601

About: Hi! My name is Kayla, and I've been a lifelong lover and caretaker of dogs and cats. Throughout my life, I’ve had the pleasure of caring for a wide variety of dogs, from tiny Pomskies to robust Rottweilers, and everything in between, from playful puppies to wise seniors. At home, my husband and I have a lively little boy and two wonderful fur babies. Mila, our 8-year-old pitbull, is full of sass, while Kain, our 6-year-old American bully, believes there's no such thing as too much attention. Both are high-energy and absolutely adore people. With my extensive experience and a home full of love and energy, I understand the diverse needs and personalities of pets. I look forward to meeting your furry family members and providing them with exceptional care! I'm a dedicated stay-at-home mom with a great amount of flexibility to cater to your pet's needs. Pet care fits seamlessly into my daily routine, allowing me to give your furry friends the attention and care they deserve. I specialize in drop-in visits and dog walking, ensuring your pets are well-looked after in the comfort of their own home. Whether it's a midday walk or a quick check-in, I'll make sure your pets are happy, healthy, and engaged.

Sitter Profile Image: Allison B.
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Allison B.
from
$15
per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
15 years of experience
Stephenson, VA, 22656

Allison was amazing. Our dog, Katie loved her. She Loved her walk/runs. Great communication. Was flexible and easy to work with. Highly recommend her. Thank you.

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Joey C.
Sitter Profile Image: Kayla H.
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Kayla H.
from
$24
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
21 years of experience
Winchester, VA, 22601

Kayla is so awesome! She’s professional and great with my dog. Her cancellation policy is flexible too which is super helpful. Highly recommend Kayla as a dog walker!

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Kathleen H.
Sitter Profile Image: Jose O.
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Jose O.
from
$15
per walk
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: Karen O.
Verified Enhanced Background Check
Karen O.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
19 reviews
9 repeat clients
12 years of experience
Winchester, VA, 22602

About: At Pet Penthouse, we provide the same loving care your pets get at home. Located in the sole penthouse at the top of the Dominion Square office building, a quiet, safe, and exclusive environment is provided for your pet. Having grown up on a farm, I have a deep love for animals and an innate ability to bond with them, reducing their stress and making them feel at home. My schedule offers the flexibility to meet your needs and shower your pet with attention. What you can expect • Complete peace of mind: I completely understand the stress of leaving a family member behind. I am committed to providing exceptional care and regular updates about your fur-baby while you're away. • Meticulous care and attention to detail: Your pet's well-being is my top priority. I pay close attention to their health and behavior, noticing small changes that might signal an issue. This includes being vigilant on walks and handling any special diets. • Routine and consistency: I meticulously follow your pet's normal routine, from feeding and medication schedules to exercise and play habits. House rules, like keeping pets off the furniture, are respected because consistency is key to reducing your pet’s stress. Pet sitting isn't a side gig for me—when I am taking care of your baby, that is my sole focus. I have a flexible schedule so I am able to ensure your pet's routine is maintained and I can accommodate last-minute requests. When caring for a pet, I treat them like family, giving them full attention and making sure they feel loved, safe, and happy until you returns. You can relax knowing your fur-baby is in loving, capable hands. I have established a safe environment by pet-proofing our home by securing toxic substances and small, dangerous items. I will ensure dogs are on a leash when outside. I am always prepared to adjust activities based on weather conditions to protect the pet from heat, cold, or storms.

Sitter Profile Image: Kathy G.
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Kathy G.
from
$25
per walk
5.0 out of 5 stars
58 reviews
18 repeat clients
30 years of experience
Winchester, VA, 22601

About: I have been an animal lover & owner my entire life. I've always had a dog along with the occasional hamster, cat, guinea pig, lizard, hermit crab, rabbit, bird & fish. I love animals especially dogs. I am very comfortable with large breed dogs as well as smaller dogs too. I like to think the bigger the dog the more loves & cuddles you get.🥰 I've volunteered for rescues over the past 10 years & have fostered both dogs & cats. I'm very excited to meet new animals and their owners. I currently have 1 dog & 3 cats. I try to stick to your animal's schedule so they continue with their normal routines. I make sure your animal is given lots of attention & play time. I will show your animal affection & lots of play time & snuggling if they enjoy that. I've never met a dog that hasn't liked me....big or small.

Sitter Profile Image: Marianina G.
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Marianina G.
from
$15
per walk
14 years of experience
Winchester, VA, 22602

About: Hi, I’m Nina! My passion for animals started when I began volunteering at animal shelters when I was 13. By the time I was 19, I was working full-time at a doggy daycare where I learned puppy / senior care, light training experience, medication administration, exotic pet care, behavioral management, navigating social interactions / introductions, and much more in my 8 years there. I am currently working full time, Monday - Friday 8:30am-4:30pm but am hoping to change that soon to focus on my passion for animal care and socialization. I love hanging out and chilling with the dogs I meet and getting to know them. I will take your pets on walks, sit with them in the shade or outside, play with any toys they love, or just hang out on the couch if that’s their speed. My care is custom to your pet and their needs.

Sitter Profile Image: Sophia C.
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Sophia C.
from
$10
per walk
5.0 out of 5 stars
1 review
1 repeat client
20 years of experience
Winchester, VA, 22601

About: I love both cats and dogs and have had them my whole life! Today, I have a 4-year-old Shiba Inu that I rescued. I was given a Tuxedo cat for my fourth birthday and we got a Husky mix when I was around 10. I fed them and walked and played with them my whole childhood. When I was in college, I started fostering animals— both cats and dogs— for years on end. Some of the animals needed eye drops and oral medication which I helped administer. I even helped my mom adopt one of the cats I fostered! I promise to love and care for your pets as if they are my own! I work remotely from 2-10pm on Tuesdays-Saturdays! I’m best fit for mid-day, morning or late night walks and I am free for all-day/ overnight care on Sundays and Mondays. If I am able to work remotely from your house, I could also potentially work weekdays and weekday night. I can play with your pet and take your dog on long walks! I also have treats and toys at my disposal that I can share (per permission from the owner of course!)

Sitter Profile Image: Timothy E.
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Timothy E.
from
$15
per walk
4 years of experience
Winchester, VA, 22601

About: My dog Freckles and I would love to welcome other pups in our home, which features an open basement for dog play, a gated garage for outdoor lounging (see photos), and a small nearby park for dog walks. I work remotely from home during the week with a flexible schedule for taking the pups outside as needed. Morning and evening walks with occasional trips to the dog park. Treats throughout the day and meals as needed. Plenty of play and pets in between. I have a friendly dog named Freckles who loves to play with other dogs of all types and sizes. Dogs are allowed anywhere in the house as well as in my outdoor garage space which is gated off.

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

Dog parents share their Rover experiences - Winchester

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5.0 out of 5 stars

Thanks as always Alyssa. Yeah anytime the weather is hot, bring him in as soon as he does his business. You see he likes the fan on! Great job 👏

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James H.
Dog Walking
5.0 out of 5 stars

Kimberly takes such good care of Tucker. She always gives a detailed description of there time together. Thanks Kimberly 👍 A+++

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James H.
Dog Walking
5.0 out of 5 stars

Thank you so much for walking Willow on such short notice! I really appreciate your help and how you went above and beyond by also giving her fresh water after the walk 😊

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Heaven A.
Dog Walking
5.0 out of 5 stars

Absolutely fantastic! On time, thank ok good care of my girl and accepted in a moments notice! Definitely will be using Alexsys again!

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Robert S.
Dog Walking
5.0 out of 5 stars

James is excellent. So great in so many ways What a blessing when my back went out. James saved the day for 4 days!

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Manley N.
Dog Walking
5.0 out of 5 stars

Karen is the best! Bentley loves her. She takes her time and really cares about your pet. Thanks Karen you’ve been amazing to work with.

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Dana M.
Dog Walking
5.0 out of 5 stars

Gabriel was a life saver for my husband & I. Super responsive, great with our little dog, very trustworthy. Highly recommend :)

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Christina G.
Dog Walking
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How Rover works

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Sitters in Winchester average 3
repeat dog walking clients

FAQs for Dog Walking - Winchester

Frequently asked questions about Rover

The average cost for Dog Walking in Winchester on Rover is $21.4 per walk (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .

As of July 2026, there are 876 sitters on Rover offering Dog Walking across Winchester. 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 Winchester. 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 Winchester.

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 Winchester. On Rover:

  • 93% of walkers can help with special care needs
  • 100% 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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