House Sitting Webbtown

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

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Sitter Profile Image: Kristine S.
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Kristine S.
from
$40
per night
5.0 out of 5 stars
8 reviews
30 years of experience
Winchester, VA, 22601

Kristine was very responsible taking care of our dog and home while we were gone for 4 days. In fact, more than we expected. We will definitely want her to take of Boots again when we need a dog sitter.

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Sharon B.
Sitter Profile Image: Marianina G.
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Marianina G.
from
$30
per night
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: Hailey C.
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Hailey C.
from
$40
per night
5.0 out of 5 stars
4 reviews
10 years of experience
Winchester, VA, 22602

Hailey was reliable, sweet & very communicative. Riley was well cared for, and received updates and photos during the day. This was a good experience for my dog.

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Carmen C.
Sitter Profile Image: charlotte g.
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charlotte g.
Star Sitter
from
$40
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
8 years of experience
Winchester, VA, 22601

Our 130# Newfoundland and cat were well taken care of. Communication was great, even using a different app since we were in Europe. Would not hesitate to use Charlotte again, she cared for our animals like they were hers.

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Giovanna C.
Sitter Profile Image: Kim K.
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Kim K.
from
$76
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
40 years of experience
Round Hill, VA, 20141

Kim was amazing with our high maintenance little dachshund. We are so appreciative of her attentiveness, kindness, and professionalism. Your pup will be in great hands with Kim!

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Amalio C.
Sitter Profile Image: Aly P.
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Aly P.
Star Sitter
from
$40
per night
5.0 out of 5 stars
32 reviews
12 repeat clients
16 years of experience
Martinsburg, WV, 25405

Aly was an absolute joy. She took such good care of both my dogs, one of which is elderly and she made sure she got her meds and any other instructions I left. I got daily updates with lots of pictures, including taking my other dog on car rides in the country! She gave each pet - including my fish! Individual attention and care. I can’t say enough about her and will use her again!

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Anne B.
Sitter Profile Image: Caitlin M.
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Caitlin M.
from
$60
per night
5.0 out of 5 stars
75 reviews
29 repeat clients
15 years of experience
Winchester, VA, 22601

Caitlin surpassed our expectations! She gave us peace of mind our fur babies were fully taken care of. She made sure to keep me in the loop with updates and the most adorable pictures. She even brought extra treats that became a favorite. I would recommend her to anyone and hope to use her again in the future! Thank you Caitlin for everything! I know Bear and Coco miss you!

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ReNew C.
Sitter Profile Image: Sarah W.
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Sarah W.
from
$36
per night
5.0 out of 5 stars
4 reviews
1 repeat client
2 years of experience
Harpers Ferry, WV, 25425

About: Ever since I was a child, I have loved animals and taking care of them has always come naturally to me. I give attentive, affectionate, and thorough care to all animals I am given the pleasure of working with! I have had a senior dog in the past, so administering medications to a pet is a task I am comfortable with and accustomed to. I am passionate about caring for and working with animals, dogs, cats, and otherwise, and I hope to be able to care for yours soon! I am a recent college graduate, so I have a decent amount of time during the day and evenings to watch, play, and take care of your pets! Weekends before 4:00pm and weekdays before 6:30 work best for me, but I am also available some other times depending on when you need me. I have had many dogs with various energy level and various health conditions. I am more than comfortable providing high energy walks, low energy snuggles, and administering various medications if necessary. I am also more than comfortable giving plenty of love, treats, and head scratchies to your pets on request!

Sitter Profile Image: Haleigh S.
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Haleigh S.
from
$32
per night
5.0 out of 5 stars
2 reviews
1 repeat client
3 years of experience
Charles Town, WV, 25414

About: I have had a disabled dog of my own since I was 8, he has seizures frequently. I also have dog sat for my neighbor on multiple occasions, of which was very large, required medication, and emotional support for her anxiety. I work part time at a restaurant so I have more than enough time to provide high quality and detailed care to your furry family members. If I work, they're typically nights, so I am more available during the day or after I get off work to do some final check ins with the pets before bed. As the care would only happen in your home, I take great pride in leaving the home better than I found it and ensuring your pets health, comfortability, and safety with the information and materials provided to me.

Sitter Profile Image: Linda K.
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Linda K.
from
$60
per night
5.0 out of 5 stars
115 reviews
46 repeat clients
18 years of experience
Winchester, VA, 22602

About: (Formerly Kamp Kelley) I have been fostering small dogs for a rescue group in No. VA. for the last 9 years (my aching back doesn’t allow me to work with dogs larger than 20 lbs)--prior to that I fostered cats and kittens. I has experience with many types of small dogs—especially Shih Tzu’s and Llasa Apso’s, but also Yorkshire Terriers, Basset Hounds, Pom's, Toy Poodles, etc. My expertise is in rescuing and caring for senior and special need dogs. Since I have a dog-friendly house and a large-fenced yard (1/4 acre) for them to run and play in, I decided to become a dog-sitter 5 years ago. I believe in loving and treating your fur-baby like my own! We keep her home and yard dog proof so your little angel will be in a safe, relaxed, dog-friendly, and loving environment! Because I am retired, my schedule is very flexible. I'm retired and except for occasional trips to the store, bi-weekly Bridge games. monthly book group and a occasional meeting, I'm home ALL THE TIME. At this point, I am accepting only ONE dog at a time EXCEPT if there are 2 dogs from the same household. Same for cats. I have a large, fenced yard that can be separated off. I have lots of dog equipment. For example large crates if your dog is used to being crated, bowls, beds and cushions, a big bed for them to share with me, jackets, leashes, kongs and lots of love and affection. Same for cats--EXCEPT, I let them out only on the back deck (enclosed).

Sitter Profile Image: Sierra C.
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Sierra C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
7 years of experience
Boyce, VA, 22620

Sierra took amazing care of my pups at my house while I was out of town for a few days!

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McKenna C.
Sitter Profile Image: Victoria L.
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Victoria L.
from
$35
per night
4.8 out of 5 stars
7 reviews
1 repeat client
23 years of experience
Winchester, VA, 22602

Victoria provided frequent comms and was very responsive. Great job, we will definitely use her again!

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Stu Y.
Sitter Profile Image: Vicki T.
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Vicki T.
from
$50
per night
5.0 out of 5 stars
10 reviews
5 repeat clients
30 years of experience
Harpers Ferry, WV, 25425

Vicki was great, Will most certainly use her again.

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Dustin K.
Sitter Profile Image: Alexandria Y.
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Alexandria Y.
from
$65
per night
4.9 out of 5 stars
19 reviews
8 repeat clients
3 years of experience
Bluemont, VA, 20135

Took great care of my dogs when I was out of town and very responsive the entire time! Would recommend Alexandria to anyone!

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Leah S.
Sitter Profile Image: Shannon B.
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Shannon B.
from
$55
per night
5.0 out of 5 stars
5 reviews
5 years of experience
Winchester, VA, 22602

Shannon was amazing. Our little guys loved being with her. Def will be using her again. Her communication about what the dogs were doing was great. Highly recommend

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Melissa S.
Sitter Profile Image: Stefany P.
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Stefany P.
from
$60
per night
3.7 out of 5 stars
3 reviews
5 years of experience
Winchester, VA, 22602

About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)

Sitter Profile Image: Julia Z.
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Julia Z.
from
$60
per night
4.9 out of 5 stars
22 reviews
6 repeat clients
5 years of experience
Winchester, VA, 22601

Julia was very patient with our dog while he needed to be on Benedryl the first few days and wasn't quite himself. She kept us updated, left our house clean upon leaving, and our dog loved snuggling and watching tv with her.

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Brooke H.
Sitter Profile Image: Marsha B.
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Marsha B.
from
$60
per night
5.0 out of 5 stars
5 reviews
40 years of experience
Purcellville, VA, 20132

About: Hi! I’m a reliable, patient, and experienced pet lover who treats every animal like family. Whether your pet is high-energy and playful or calm and cuddly, I adjust to their personality and needs to make sure they feel safe, happy, and loved while you’re away. I have experience caring for dogs of all sizes, ages, and temperaments, as well as cats and other small pets. I’m comfortable with administering medications, sticking to specific feeding schedules, long walks, crate training, senior care, and puppy routines. Your pet’s safety and comfort are always my top priorities. You can expect: • Plenty of exercise and playtime • Consistent routines • Clean food and water bowls • Lots of affection and attention • Regular photo and video updates I understand how important it is to trust someone with your pet, and I take that responsibility seriously. I communicate clearly and promptly so you can relax knowing your furry family member is in good hands. I’d love to meet you and your pet! Feel free to reach out with any questions — I’m happy to schedule a meet-and-greet to make sure it’s a perfect fit. I’m currently working part time and am available for drop ins, walks and cuddles Thursday - Sundays - I am happy to overnight board as well I have a fenced yard with 3 acres and beautiful country roads for strolling and spending quality time with your pup - we currently do not have pets

Sitter Profile Image: Zeel L.
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Zeel L.
from
$60
per night
4.9 out of 5 stars
12 reviews
3 repeat clients
20 years of experience
Charles Town, WV, 25414

About: Hi, I'm restarting my animal care business. I want to ensure a stimulated experience with a swift pace and consistent disciplined walking style of what I like to refer to as "nose to toes," where the dogs stay no further than my toe, to my sides, or behind me. I also have experience with aggressive dog behavior, so if a single walk is necessary, I can do that. I have been in the animal care business for as long as I can remember, and I know Fairlington very well since I grew up here. I now live in Harper's Ferry in West Virginia. I will be able to track my walks with a phone app that will track your dog's walking pace, distance traveled, and the route we take. I usually do pack walks of 3-5 dogs depending on size, but I can do singles if needed. I'm also able to cat-sit/dog-sit and care for exotics and birds (no insects). I'm flexible because I have my own cleaning/organizing/declutter business. I wake up however early dog might need be let out or pet given meds, and give at least 3 long 30min-hour walks depending on the energy level and few let outs throught the day if needed for young pups or older if bladder is sensitive. Plenty of loves and can work on training or stimulated play time with toys and puzzles. I will be professional and not have any guests over ever, and always keep doors locked when not there and if plants need care I can help with watering. I have 4 animals myself so it's pretty automatic to just add another pet cuz I've cared for multiple animals at a time or drop in visits when needed throughout my day. Whatever the fmaily requests for schedule when to feed, medicate(if needed), amount of walks and play time needed to make sure they're healthy and stimulated. Whenever they're ready for bed, crate if needed requested by parents, and make sure they go outside(dogs) to ensure no accidents throughout the night. I give them just as much love and attention and play as my own. And feed round same schedule unless instructed otherwise. Giving exercise and play time when needed. And kept to routine of crating if owners instruct.

Sitter Profile Image: Lauren H.
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Lauren H.
Star Sitter
from
$125
per night
5.0 out of 5 stars
111 reviews
51 repeat clients
34 years of experience
WV, 25413

This is my second time using Lauren for in-home overnight stays for my two (very spoiled) Schnauzers. I could not be happier! I felt so comfortable after the first stay that I didnt hesitate booking a weekend getaway. You will not be disappointed!

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Lisa N.
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The median cost per night for house sitting in Webbtown is $50

Pet parents share their Rover experiences - Webbtown

1 / 1
5.0 out of 5 stars

Annalee is an incredible sitter! She house sat and cared for my dog for a week and a half. She took my dog on lots of walks and gave her so much love, care, and attention. I really appreciate the daily updates and pictures. She was also very respectful of my home and things and left my home just as she found it. She is definitely my go-to sitter for the future! I greatly appreciate her!

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Michelle M.
House Sitting
5.0 out of 5 stars

Highly recommend! Annalee was super accommodating, kept me updated the whole time, and took amazing care of my dog. I felt comfortable and a peace of mind knowing my pup was being well taken care of. I’ll definitely book with her again!"

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Macy M.
House Sitting
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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 sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  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

Sitters in Webbtown average 4
repeat house sitting clients

FAQs for House Sitting - Webbtown

Frequently asked questions about Rover

As of July 2026, there are 1,482 sitters on Rover offering House Sitting across Webbtown. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Webbtown walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Webbtown maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Webbtown choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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 sitter 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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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 sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters 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 sitter.

Yes, you can find sitters who have experience with handling special pet needs in Webbtown. On Rover:

  • 95% of sitters 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.

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