House Sitting Chester Gap

Find a loving house sitter to watch over your pets and your home.

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Over 24
pet parents in Chester Gap have booked house sitting

Chester Gap, Find top rated house sitting

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: 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
Front Royal, VA, 22630

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: Carissa T.
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Carissa T.
Star Sitter
from
$35
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
3 years of experience
Front royal, VA, 22630

We were on vacation with our high-anxiety pup and Carissa was happy to help us out - she's a great communicator and we appreciate her willingness to come up to our Airbnb in the mountains!

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Leslie H.
Sitter Profile Image: Janna A.
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Janna A.
from
$31
per night
11 years of experience
Front Royal, VA, 22630

About: Ive had pet dogs since the age of 10. I love all types of aniamls! I would love to take care of your animal and have you and your pets’ needs met! Im currently unemployed so I can make time for your pets whenever is needed! My schedule is flexible and am willing to work with you! Ive always gotten along great with any and every animal i meet! I live right next to a park, so I am able to take them there whenever to get some energy out and just make sure they are happy! I am able to work with you and I can watch your pets at your home or take them to my home if needed!

Sitter Profile Image: Sherry R.
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Sherry R.
from
$45
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
3 years of experience
Stephens City, VA, 22655

She is awesome. Did a great job, knowledgeable, very nice. Will definitely use again sometime.

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

Kristine is a warm and caring individual and my dogs picked up on that immediately. She was fantastic with our three German Shepherds. She took great care of our dogs and our home while we were away. She was respectful of our property, cleaned up after herself and the dogs, and went above and beyond by mopping up after a rainstorm and even throwing linens in the wash before we returned. It gave us so much peace of mind knowing everything was being handled so thoughtfully. Great communication, too. I would absolutely book Kristine again and highly recommend. Kristine, if you’re reading this, thank you so much for putting up with all the shedding, the Shepherds were dropping their coats like crazy.

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Alesha R.
Sitter Profile Image: Megan S.
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Megan S.
Star Sitter
from
$75
per night
5.0 out of 5 stars
90 reviews
29 repeat clients
10 years of experience
Stephens City, VA, 22655

Megan is an absolute treasure!! And that’s with a T not a P. Although she was also a pleasure to work with she is one of the most capable, friendly, caring, conscientious, pet sitters I have ever met. I will definitely use her again. I say treasure because she’s the sitter I would want again and again and again. 10/10 🥰🥰

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Amanda B.
Sitter Profile Image: Darian C.
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Darian C.
from
$65
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
20 years of experience
Strasburg, VA, 22657

Thank you so much! Darian was great with the pups and took care of both them and our house with the utmost care. She was also very responsive and really helped out us out of a jam, our sitter cancelled at the last minute and she stepped up and made it work!

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Patrick W.
Sitter Profile Image: Victoria K.
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Victoria K.
from
$20
per night
1 year of experience
Front Royal, VA, 22630

About: Hello! I am 23 years old and when I was 15-17 I helped train dogs including a service dog. I love all dogs and will always love your dog as well! I am looking for any opportunities that involve dog walking or dog sitting! I do not have my own dog but would love to have a golden retriever later in life! I am currently available all throughout June and July. August 3rd I will be unavailable because I start a nanny job that will be full time. I am just looking for specifically summer hours in June and July. I will help feed, get into crate, or “space”, if needed train, and go for walks with the dog. I will help in anyway I can.

Sitter Profile Image: Laura W.
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Laura W.
from
$65
per night
17 years of experience
Linden, VA, 22642

About: Dogs and cats love me. And I love them. I recently relocated from the West coast to East. have volunteered at Laguna Beach Animal Shelter in California the past nine years. There are many pets in my household ( one dog, 4 cats)). I thoroughly enjoy pet/home sitting and am grateful for your trust. I am flexible and can easily adjust my schedule accordingly. Overnights are my specialty. I have no pets or children of my own thereby emplyment is my only commitment. My household has pets and roommates travel extensively so I feed, love and whatever other pet needs arise. I am and happy to accommodate as it takes a village with pets!

Sitter Profile Image: Sara G.
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Sara G.
from
$60
per night
3.0 out of 5 stars
2 reviews
5 years of experience
Front Royal, VA, 22630

We can’t recommend Sara enough! She recently cared for our two dogs, Frankie and Lulu, as well as our fish, and went above and beyond by making sure the bird feeder was stocked for the wild birds. Her attentiveness and thoughtfulness were evident from day one. She sent us daily updates and plenty of pictures of Frankie and Lulu, which kept us reassured and connected while we were away. It was clear Sara treated our home and pets as if they were her own. Frankie and Lulu were happy and relaxed when we returned, and everything in the house was spotless. Knowing our pets were in such good hands made our time away completely stress-free. We’re so grateful for Sara and would absolutely trust her again in the future!

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Jill B.
Sitter Profile Image: Cathy W.
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Cathy W.
from
$55
per night
5.0 out of 5 stars
9 reviews
1 repeat client
8 years of experience
Front Royal, VA, 22630

About: I love dogs and have worked with several families walking dogs in the mornings, afternoons amd lunch breaks. I have a 4 year old Pomeranian named Milo. He’s 5 pounds. He won’t be with me on walks or staying over at your house dog sitting. I’m very passionate about animals and love everyone of them like they’re my own. I will love on your babies and we’ll have a great time together. I love playing fetch and giving snuggles. If you have any questions please feel free to reach out to me. I’m not working at this time so I’m available Monday thur Saturday for walks. I can do walks or let out your pet if you perfer in your yard. I’m also available for sleepovers with your fur baby. I live on almost 4 acres now and a fenced in yard. I have my Pom. My mom is also living with me now in a basement apartment and she has two smaller dogs that are very friendly. They will be kept in the basement if I’m watching other dogs or having sleepovers. They will also be let out at separate times to put everyone’s mind at ease.

Sitter Profile Image: Taylor R.
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Taylor R.
from
$65
per night
15 years of experience
Winchester, VA, 22601

About: I’ve taken care of dogs and cats of all sorts. I grew up with small, medium, and large dogs as well as indoor and outdoor cats. I’ve also grown up caring for animals from a variety of backgrounds- fosters, rescues, you name it. I genuinely love spending time with animals and since I can’t have one of my own this seems like a great way to connect with pets and offer my services. I’m happy to come meet any animals in advance to make you more comfortable. I currently work remotely 90% of the time so this gives me a lot of flexibility to walk and take care of animals during work day hours if needed. I’m very good with following whatever directions will make you and your pets feel the most comfortable in your homes and out on walks.

Sitter Profile Image: Pam N.
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Pam N.
from
$68
per night
4.9 out of 5 stars
23 reviews
10 repeat clients
20 years of experience
Marshall, VA, 20115

Pam took great care of our pups and left our house looking amazing. She also communicated frequently!!

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Molly D.
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 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.
Sitter Profile Image: Kathryn W.
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Kathryn W.
from
$50
per night
5.0 out of 5 stars
2 reviews
10 years of experience
Winchester, VA, 22601

Katherine was absolutely great with Donner and Murphy during the storms we had yesterday. Played with them cuddled with them to comfort them. We’ll definitely have back as needed.

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Pamela T.
Sitter Profile Image: Katie H.
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Katie H.
from
$31
per night
8 years of experience
Marshall, VA, 20115

About: I have been house and pet sitting since I was in high school. Friends, family, and neighbors are always asking if I can care for their animals and homes! I used to shadow a family friend who had a pet sitting business and I loved tagging along! I work full time as a teacher, but I get off at 2:35 so my weekdays have free afternoons and evenings. Weekends are completely free and I’ll be able to care for your pets any time of day. I can easily commute to your home to care for your pet. I don’t mind transporting your pets if needed. I will take great care and consideration when entering your home and ensure safety, fun and love for your pets!

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: Victoria S.
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Victoria S.
from
$27
per night
5.0 out of 5 stars
1 review
6 years of experience
Winchester, VA, 22602

Victoria stayed in our home to take care of our dog Mika. She was very conscientious and respectful of place and took great care of Mika. Victoria spent most of the day with Mika so she wasn’t alone. We returned to a very calm and relaxed pup. Victoria is a good communicator, anytime she had a question or concern she was quick to let me know. We won’t hesitate to use Victoria again.

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Belinda M.
Sitter Profile Image: Caitlyn N.
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Caitlyn N.
from
$20
per night
5.0 out of 5 stars
1 review
18 years of experience
Boyce, VA, 20130

About: I’ve taken care of my dads friends dogs aswell as my own cat. I’ve fed, walked, etc.. I’d love to work with your pet! I’ve had my cat for 12 years and she’s well taken care of. This is currently my main priority as I’m going to college soon! I can do pretty much any days and any times!! Monday-Friday. 7Am- 9PM (just an example) I currently do not offer this ! But if i ever did I’d make sure your fur baby is as comfortable as my own. Thank you for trusting me!

Sitter Profile Image: Nelly C.
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Nelly C.
from
$31
per night
4 years of experience
The Plains, VA, 20198

About: I have 4+ years of experience caring for dogs and cats of all sizes and personalities. I’ve done dog walking, feeding, and overnight house sitting. I’m reliable, attentive, and make sure pets feel safe, comfortable, and loved while you’re away. I stick to their routines and give them plenty of attention, playtime, and care. I study online, which gives me a flexible schedule and plenty of time to care for your pets. I’m available for drop-ins, walks, and overnight stays, and can adjust to your pet’s routine to make sure they feel comfortable and cared for. I prioritize your pet’s safety and comfort by following their routine and keeping a calm, clean environment. I’m very attentive, make sure doors are secure, and always supervise pets. I treat your home with respect and keep you updated with photos and messages.

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The median cost per night for house sitting in Chester Gap is $50

Pet parents share their Rover experiences - Chester Gap

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5.0 out of 5 stars

Leonarda takes such great care of our fur babies! She always arrives on time and gives our two dogs love while we are not home. Additionally she takes very good care of our home while she stays here. It is a relief to know our dogs and home are taken care of while on vacation!

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Alex T.
House Sitting
5.0 out of 5 stars

Leonarda’s just perfect. Our go-to repeat pet sitter who is full of love for our boys and always very professional.

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Peppy K.
House Sitting
5.0 out of 5 stars

Leonarda was an incredible sitter for Nova! She stepped in last minute for a 5-day stay and was so communicative and responsive the entire time. I got plenty of updates and great photos, which made me feel very at ease. Nova was clearly well cared for, and my place was left super tidy and organized when I got back. I’d absolutely book with her again!

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Henry L.
House Sitting
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Meet local sitters who will treat your pets like family

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Popular requests for house sitting - Chester Gap

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Sitters in Chester Gap average 3
repeat house sitting clients

FAQs for House Sitting - Chester Gap

Frequently asked questions about Rover

The average cost for House Sitting in Chester Gap on Rover is $74.93 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting 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 House Sitting. For more information on service fees, click here .

As of July 2026, there are 818 sitters on Rover offering House Sitting across Chester Gap. 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 Chester Gap 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 Chester Gap 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 Chester Gap 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 Chester Gap. On Rover:

  • 90% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 92% 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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