House Sitting Pyletown

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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: charlotte g.
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charlotte g.
Star Sitter
from
$40
per night
5.0 out of 5 stars
5 reviews
2 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: Hailey C.
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Hailey C.
from
$40
per night
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: 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: 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: Kristi R.
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Kristi R.
from
$30
per night
5.0 out of 5 stars
26 reviews
10 repeat clients
20 years of experience
Stephens City, VA, 22655

Brenna was a wonderful pet sitter to our dog, Rocky over the weekend! She kept me up to date on how he was doing and sent me plenty of pictures and videos of him having a wonderful time! I knew Rocky was safe and being taken care of while in Brenna's care and I truly I appreciate that. Thanks again!!!

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Destiny W.
Sitter Profile Image: Reina P.
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Reina P.
from
$47
per night
4.9 out of 5 stars
28 reviews
8 repeat clients
10 years of experience
Boyce, VA, 22620

About: Hi, My name is Reina, I recently retired and love to care for pets. I have a lot of time and dedication to care for yours. Flexible with schedules. I am currently retired, so I have a lot of time to play and properly care for your pet. I do not have pets anymore since my sweet dog passed away.I am ready to give the same kind of love and attention to yours. I have a fence yard and a very clean environment.I do not have pets anymore since my sweet dog passed away.I am ready to give the same kind of love and attention to yours.

Sitter Profile Image: Kristine S.
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Kristine S.
from
$30
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: Caitlin M.
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Caitlin M.
from
$90
per night
3 years of experience
Winchester, VA, 22602

About: I’m a certified Physician Assistant with a strong medical background and CPR certification, so your pet’s safety is always my top priority. I’ve cared for pets for years, including dogs and cats of all ages, and I’m comfortable with feeding, walking, playtime, medications, and general care. I’m reliable, attentive, and love spending time with animals, whether that’s keeping them active or giving them extra cuddles. I treat every pet like my own and will always keep you updated so you feel comfortable while you’re away. I currently have a very flexible schedule, which allows me to provide consistent, attentive care throughout the day. I’m available for drop-ins, walks, and extended visits during weekdays and weekends. I can easily accommodate your pet’s routine and provide frequent check-ins, playtime, and companionship so they’re never left alone for long periods. Your pet’s safety and comfort are my top priorities. As a certified Physician Assistant, I’m trained to stay calm, attentive, and responsive in any situation. I carefully follow all care instructions, including feeding schedules, medications, and routines. I respect your home and your pet’s environment, and I take time to build trust, especially with shy or anxious pets. I’ll always keep you updated so you feel confident while you’re away.

Sitter Profile Image: Linda K.
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Linda K.
from
$60
per night
5.0 out of 5 stars
114 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: 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: 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: Sydney C.
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Sydney C.
from
$40
per night
10 years of experience
Winchester, VA, 22602

About: I’ve had both dogs and cats my entire life and genuinely love caring for animals of all ages and personalities. I’m experienced with feeding, walking, bathing, cleaning up after pets, administering lots of love and attention, and making sure they feel safe and comfortable while you’re away. I understand that every pet has their own routine, and I’m happy to follow any instructions to keep them happy and healthy. Whether your pet loves playtime, long walks, or just wants someone to cuddle with, I’ll care for them as if they were my own. I work Monday-Friday 8-5. I can take care of your pet(s) before and after work. On weekends I can spend even more time with your furry family!! I feel comfortable going to client’s houses to pet sit! I have pet sit for my aunt multiple times for her two pups— including a dog with a strict diet and medication for his seizures.

Sitter Profile Image: Kim K.
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Kim K.
from
$48
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
40 years of experience
Round Hill, VA, 20141

About: I started taking care of neighbors' and friends' dogs, cats, fish, hamsters and birds when I was 14 years old. I love animals and wildlife of all kinds. I have been a cat and dog mom for 28 years and have had 2 leash and dog-reactive dogs (strong, 60 pound+ mutt and pit bull) so I am experienced in dealing with these situations. I have strong situational awareness with my head on a swivel when walking dogs. My senior kitty required specialized medical care at the end of her life with daily prescription medication and subcutaneous fluids. I have volunteered as a dog walker and cat snuggler at Friends of Homeless Animals rescue. I have been a social worker for 30 years and am nearing retirement from full-time employment. I would love to use my love of animals to continue working as a pet-sitter and dog walker. I am very organized, detail-oriented and will care for your pet as I care for my own. I would love to meet you and your pets to see how I can be of service. I currently work full-time Monday through Friday but am retiring at the end of September. My weekends are currently free. I have some flexibility in my weekday schedule so I may be available on a case-by-case basis for weekday dog walks that are in western Loudoun County and within a 10 minute drive of my home. I will care for your pet in your home so that they will be the most comfortable. I am available for overnight stays to keep your pet company and to provide close supervision, lots of TLC, food, water, potty breaks and anything else you may need. I am a non-smoker and non-drinker. I am very detail-oriented, responsible and dependable. As a bit of an overprotective dog mom, I have needed to entrust my dog's care to a pet sitter. My dog is my world. So I know just how valuable trust, dependability and attention to detail are. What matters to you matters to me. I will follow your instructions down to the smallest detail. I will be diligent in communicating with you, sending regular updates and photos of your pet so that you know they are safe and happy in my care.

Sitter Profile Image: Matthew H.
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Matthew H.
from
$30
per night
5.0 out of 5 stars
2 reviews
1 repeat client
7 years of experience
Reseda, Stephens City, VA, 22655

About: I am a husky lover and owner who has spent most of my life taking care of dogs! I am 30 years old and have grown up taking care of beagles as well as pet sitting for family members and neighbors. Now, I currently have two huskies, ages 3 and 1. I enjoy long walks with my pups and lots of play time! On the weekends, I enjoy taking my dogs on long hikes, taking them to the dog park for some play time and even runs on the beach. My huskies are friendly with dogs their size and love making new friends. They also have spent time around cats and although they avoid playing, they do love other furry friends. My energetic attitude and love for animals makes me the best match for the job.

Sitter Profile Image: Suellen W.
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Suellen W.
from
$40
per night
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: Julia Z.
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Julia Z.
from
$60
per night
4.9 out of 5 stars
21 reviews
6 repeat clients
5 years of experience
Winchester, VA, 22601

Julia is wonderful with our cat and taking care of our home while we are out of town. She kept us up-to-date throughout each day with photos and even a video of our little guy. She was very prompt and great at communication. Thank you so much, Julia!

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Kristyn A.
Sitter Profile Image: Taylor S.
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Taylor S.
from
$50
per night
5.0 out of 5 stars
23 reviews
9 repeat clients
12 years of experience
Boyce, VA, 22620

Can’t recommend Taylor enough. She was great at dog-sitting our 1yo Samoyed pup. She communicated well, followed our instructions to a T and gave our pup lots of love.

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Tj J.
Sitter Profile Image: Haley Z.
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Haley Z.
from
$55
per night
5.0 out of 5 stars
139 reviews
45 repeat clients
17 years of experience
Stephens City, VA, 22655

Haley was amazing with our dogs and our home! This was our first time using Rover and we were a bit nervous leaving them with someone new, but truly couldn’t have found a better fit. The pups were SO excited to have a new buddy and warmed up to her immediately (they were sad when she didn’t come back after we returned home!). Haley took great care of our home, keeping it safe and clean while we were away. She went above and beyond in her professionalism and in sending daily photo updates on how the pups were doing — such peace of mind! My husband and I are both veterinarians and would recommend Haley to anyone looking for a trustworthy pet sitter!

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Chantal G.
Sitter Profile Image: Kathy G.
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Kathy G.
from
$75
per night
5.0 out of 5 stars
58 reviews
18 repeat clients
30 years of experience
Winchester, VA, 22601

Kathy took excellent care in our home of our 6-month old puppy, as well as our 3 adult cats, 1 kitten and 1 hamster while we were out of town for 5 nights. She carefully reviewed and followed all care instructions. She took good care of our home also. She was responsive, respectful and courteous at all times. She sent regular updates and photos, and messaged us with questions as appropriate. We would not hesitate to request her services again.

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Michael A.
Sitter Profile Image: Destiny F.
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Destiny F.
from
$65
per night
5.0 out of 5 stars
3 reviews
1 repeat client
12 years of experience
Stephens City, VA, 22655

Destiny was absolutely fantastic! She took great care of our babies and they all loved her! She was very communicative, gave great updates everyday, and very responsive! Highly recommend her for your pet sitting needs!!

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Kayla G.
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The median cost per night for house sitting in Pyletown is $50

Pet parents share their Rover experiences - Pyletown

1 / 1
5.0 out of 5 stars

Sierra took great care of our dog Stella! We returned home to a happy dog. Highly recommend and will definitely be reaching out again.

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Samantha B.
House Sitting
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  • 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.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

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Sitters in Pyletown average 4
repeat house sitting clients

FAQs for House Sitting - Pyletown

Frequently asked questions about Rover

As of July 2026, there are 937 sitters on Rover offering House Sitting across Pyletown. 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 Pyletown 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 Pyletown 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 Pyletown 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 Pyletown. On Rover:

  • 97% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 95% 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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