House Sitting in Chester Gap

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

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Top rated Chester Gap house sitters

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: Molly S.
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Molly S.
from
$30
per night
5.0 out of 5 stars
3 reviews
7 years of experience
Front Royal, VA, 22630

About: What sets me apart is my personal experience with dogs of all sizes, temperaments, and life stages. I’ve raised and cared for five dogs throughout my life, including Labs, Golden Retrievers, Chihuahuas, and German Shepherds, so I understand the very different needs of small, medium, and large breeds. I trained my own puppy from 8 weeks old, teaching her a wide range of tricks and good behaviors, which gave me a lot of patience and training skills. I’m also comfortable handling more challenging dogs as one of my Chihuahuas was very aggressive, which taught me how to read body language and safely manage reactive pets, from a young age. In addition, I have extensive experience caring for senior dogs. I’ve helped raise multiple dogs into old age, including a German Shepherd that lived until 15, and a Labrador Retriever that lived until 17! I understand the gentleness, and care older dogs require. Overall, I bring a lot of confidence to this role because of my genuine understanding of dogs at every stage of life. I just finished my undergrad and plan to be home all summer. I begin graduate school in the fall online and will practically have no big everyday commitments. I have a few vacations planned but besides that I am an open book willing to work anytime. When caring for pets in a client’s home, I prioritize keeping their routine as consistent as possible. (Dogs know their schedule!) I follow all instructions closely and carefully for any specific care needs. I make sure pets get plenty of attention, exercise so they feel comfortable while their owner is away. I have cared for dogs that experience extreme distress from their owner being gone and I have developed my skills to better care for dogs experiencing this. I’m also very attentive to behavior and health, so I can quickly notice if something seems off. I respect my client’s home by secure and exactly as I found it. My goal is to make both the pet, and the owner feel completely at ease, just as I would want if my dog was being watched.

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: Jessica M.
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Jessica M.
from
$40
per night
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Winchester, VA, 22601

Was gone for about 3 days. Jessica was able to provide me with a morning and afternoon report on how my pets were doing and sent me plenty of pictures. I was so grateful and was able to enjoy my trip knowing that they were in good hands. My 2 cats and pup were so comfortable with her. Definitely recommend and will rebook again!

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Jessica N.
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: Sara G.
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Sara G.
from
$50
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: Virginia S.
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Virginia S.
from
$100
per night
4.9 out of 5 stars
50 reviews
18 repeat clients
20 years of experience
Front Royal, VA, 22630

Virginia was able to take care of our pooches for us during a recent overnight camping trip. As soon as she came over to meet the dogs before our trip, we knew they'd be in perfect hands. They both immediately loved her and I am definitely one of those people who trust my dogs' instincts when it comes to people :-) Both of them immediately start vying for her attention and I knew there was no way they'd even notice we were gone. We were so happy to have Virginia close by and able to watch our pups. We'll definitely be working with her again!

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Chantharaphon V.
Sitter Profile Image: Megan S.
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Megan S.
Star Sitter
from
$75
per night
5.0 out of 5 stars
89 reviews
27 repeat clients
10 years of experience
Stephens City, VA, 22655

Megan is the best. I never have to worry about leaving my baby girl thanks to her. Megan always takes such great care of her and sends me updates consistently. Highly recommend her!

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Cody F.
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: Sierra C.
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Sierra C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 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: Jocelyn J.
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Jocelyn J.
from
$50
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
17 years of experience
Edinburg, VA, 22824

Jocelyn did a fantastic job looking after my fur babies. Easy to work with and good communication.

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Donald H.
Sitter Profile Image: Kristine S.
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Kristine S.
from
$30
per night
5.0 out of 5 stars
6 reviews
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: Pam N.
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Pam N.
from
$68
per night
4.9 out of 5 stars
22 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: 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: 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: Xavier J.
Verified Background Check
Xavier J.
from
$54
per night
6 years of experience
Purcellville, VA, 20132

About: I have over 100 hours of volunteer experience at the Middleburg Humane Foundation, where I spent countless hours walking, feeding, and socializing a wide range of breeds, ages, and sizes of dogs. I also received certification to walk dogs of different temperaments and sizes. In addition, I have over 6 years of experience in dog sitting and walking for my neighbors. I have a genuine love for dogs of all breeds, sizes, and ages. Whether they are lazy lap dogs or playful and energetic, I guarantee great care. As a recent college graduate, I have an open schedule ready to fit in with your schedule. I am available mornings, afternoons, evenings, and overnight! I guarantee proper clean-up and disposal during walks, and I ensure to keep your home neat and tidy. When messes occur, I am quick to clean and leave the area better than I found it. With over 6 years of experience in dog sitting and walking for my neighbors, I have a perfect track record of keeping their homes cleaner than I found them and making sure any messes have been taken care of.

Sitter Profile Image: Kathryn W.
Verified Enhanced Background Check
Kathryn W.
from
$50
per night
5.0 out of 5 stars
1 review
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: Keyaira J.
Verified Enhanced Background Check
Keyaira J.
from
$50
per night
5.0 out of 5 stars
2 reviews
2 years of experience
Warrenton, VA, 20186

Keyaira is fantastic! My dogs were so happy when we returned home and they are not easy to keep. (One of my dogs is neurotic!) Will only hire Keyaira from now on and have recommended her to many people.

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Amy M.
Sitter Profile Image: Kate N.
Verified Enhanced Background Check
Kate N.
from
$50
per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Delaplane, VA, 20144

Kate did a fantastic job taking of our house and our animals. We will definitely use her again!

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Christina B.
Sitter Profile Image: Estrella A.
Verified Enhanced Background Check
Estrella A.
from
$33
per night
6 years of experience
Old Tavern, VA, 20198

About: I have hands-on experience caring for dogs and cats of all ages, from energetic puppies to senior pets needing extra patience and attention. I focus on creating a calm, safe, and loving environment that keeps pets comfortable while their owners are away. What sets me apart is my ability to adapt to each pet’s unique personality and needs. I’m comfortable with basic puppy training, leash walking, administering medication, and following detailed feeding or care routines. I also have experience caring for senior pets, including providing gentle mobility support, monitoring health changes, and maintaining consistent routines to reduce stress. Above all, I treat every pet like family—making sure they feel secure, cared for, and happy while you’re gone. Pet care fits well into my daily routine. I work during the day and am available after 5:00 PM on weekdays, which allows me to provide evening walks, feeding, playtime, and check-ins. I’m also available on weekends with flexible scheduling for longer visits, overnight stays, or extended care when needed. I make sure to plan my schedule carefully so I can give each pet my full attention and maintain consistent, reliable care. I prioritize safety, trust, and a calm environment in every pet care situation. In a client’s home, I follow all instructions closely to keep pets comfortable in their familiar surroundings. I make sure doors and gates are secured, maintain a clean space, and always supervise pets during walks, feeding, and playtime. At my home, I have a Siberian Husky, so I’m very familiar with active, high-energy dogs and understand the importance of structure, exercise, and safe introductions. Above all, I focus on building trust through consistency, clear communication with owners, and treating every pet with patience and respect.

Sitter Profile Image: grace f.
Verified Enhanced Background Check
grace f.
from
$32
per night
21 years of experience
Purcellville, VA, 20132

About: I grew up with 2 Labrador retrievers, who I grew a special bond with where I grew to love taking care of dogs! I now have a 3 year old German Shepherd pure bred, who I raised and helped to train. I just adopted a Hound, who is a 2 year old rescue. I love walking my dogs everyday, and also driving them to parks as well. I feed my dogs everyday, and have always been known to be taking care of dogs my whole life. I am 21 years old, and a student at East Carolina University. I come home very often, especially during breaks, and live here all summer! My pets are apart of my everyday life, and I am willing to take care and spend valuable time with pets whenever needed and necessary for you! I am willing to do just about anything with your pets, such as spending time playing with them, walking them, going to a park, feeding them, making sure they go to bed safe, whatever fits you and your pets needs!

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Chester Gap pet parents share their Rover experiences

1 / 1
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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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 house 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.

Sitters in Chester Gap average 3
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Chester Gap on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

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

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

As of Jun 2026, there are 240 house sitters in Chester Gap. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 88% of Chester Gap house sitters respond in under an hour.

House sitters in Chester Gap have an average of 15 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Chester Gap.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Chester Gap house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

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

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

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