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.

1 / 1
Sitter Profile Image: Cobie O.
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Cobie O.
from
$50
per night
4.9 out of 5 stars
• 31 reviews
12 repeat clients
6 years of experience
Front Royal, VA, 22630

“Stayed with my dogs so they wouldn’t have to be cooped up while we traveled. It’s a relief knowing someone is there with them, particularly someone my dogs love! Will definitely be booking again!”

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Mallory F.
Sitter Profile Image: Olga & Stepan A.
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Olga & Stepan A.
from
$45
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
10 years of experience
Sperryville, VA, 22740

“Olga and Stepan took great care of both Loki my families cat and Rithie my dog. Asked very good questions on their care and comforted my dog when there was a thunderstorm :) I will absolutely be booking them agian”

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Sarah S.
Sitter Profile Image: Mary W.
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Mary W.
from
$30
per night
7 years of experience
Front Royal, VA, 22630

About: I grew up on a farm, so being around animals has always been a big part of my life. I’m a VetBloom Certified Veterinary Assistant, one of the few NAAVTA-approved programs, and I spent the summer working at a small animal hospital. I have experience with all kinds of animals and I’m comfortable handling everything from everyday care to the occasional high-maintenance personality. I’m reliable, experienced, and genuinely enjoy being around animals.! 🐶 Schedule I currently work part time from home, which gives me plenty of flexibility throughout the day. I love taking breaks to give your pup attention, playtime, walks, and companionship! Oops 😂 then definitely don’t claim that. We can make it about your approach to safety and caring for pets in their home, which is probably even better for Rover. 🐾 Schedule I currently work part time from home, so I have plenty of flexibility throughout the day. I love taking breaks to give your pup attention, playtime, walks, and plenty of companionship! 🏡 Safety, trust & environment I want every pet to feel safe, comfortable, and cared for while they’re with me. I’m happy to follow your pet’s normal routine, feeding schedule, house rules, and any special instructions you provide. Or, if you want it to sound more personal and less professional: Your pet’s comfort and safety are my top priorities! I’ll take the time to learn their routine, personality, and needs so they feel comfortable and cared for while you’re away.

Sitter Profile Image: Megan S.
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Megan S.
from
$75
per night
5.0 out of 5 stars
• 93 reviews
29 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: Darian C.
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Darian C.
from
$65
per night
5.0 out of 5 stars
• 18 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: Sierra C.
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Sierra C.
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: Sherry R.
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Sherry R.
from
$63
per night
5.0 out of 5 stars
• 21 reviews
8 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: Elyssa H.
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Elyssa H.
from
$100
per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
8 years of experience
Front royal, VA, 22630

“Elyssa thank you for great service. its wonderful to have a caring person to watch my spoiled fur babies.”

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Sheila S.
Sitter Profile Image: Scott & Sarah O.
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Scott & Sarah O.
Star Sitter
from
$120
per night
5.0 out of 5 stars
• 56 reviews
17 repeat clients
30 years of experience
Sperryville, VA, 22740

“Scott and Sarah were fantastic. I really appreciated their level of communication, care, state in which they left my home. They pay attention to the details. Every picture I received of my dogs, it looked like they were smiling ear to ear and have the best days. So cute.”

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Jecinda W.
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: Kylie C.
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Kylie C.
from
$75
per night
5.0 out of 5 stars
• 1 review
5 years of experience
Hume, VA, 22639

“My pups loved Kylie! She was very communicative and gave us updates. Definitely recommend her to watch your fur babies :)”

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Kristina M.
Sitter Profile Image: Victoria S.
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Victoria S.
from
$27
per night
5.0 out of 5 stars
• 2 reviews
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: 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: Maggie D.
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Maggie D.
from
$35
per night
10 years of experience
Front Royal, VA, 22630

About: i’ve had my own dog for 6 years and taken care of friends and family’s dogs for the past 4, whether it’s stopping in to feed them, bath them, walk them, or stay over to give them the love and affection they need. i currently work monday tuesday and thursday mornings and have the rest of the day free to care for any pet needs, and have fridays and weekends off i have a large fenced in back yard and a welcoming safe neighborhood to walk in if walks are what you’d like, the backyard is all grass and is an amazing place to let your dogs roam in to play

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: Amber H.
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Amber H.
from
$58
per night
5 years of experience
Stephens City, VA, 22655

About: Hello! I'm Amber and I love and cherish all types of creatures. I have consistently had animals in my care since a young age and will always have animals in my life. I take a personalized approach meeting your pets needs as I know each animal is unique and requires special attention. I'm happy to be available for your pets whenever necessary. Whether it's a last minute trip or a well planned in advanced event I can be there to ensure your pet has uninterrupted care and attention. I understand life can be ruff (pun a little bit intended lol) and I'm happy to lighten that burden for your precious pets. I'm all about efficiency and ensuring that your pets routines go uninterrupted despite your absence. My goal is to ease the burden and ensure you can focus on your needs. Whether this is for a vacation, a walk so you can work, or anything in between. I also value communication and transparency to ensure you know everything that goes on in your absence.

Sitter Profile Image: Isabel C.
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Isabel C.
from
$90
per night
5.0 out of 5 stars
• 19 reviews
3 repeat clients
25 years of experience
Gainesville, VA, 20155

“Beautiful job! She took such great care of our pets!!”

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Sally D.
Sitter Profile Image: Amber R.
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Amber R.
from
$65
per night
5.0 out of 5 stars
• 12 reviews
5 repeat clients
8 years of experience
Culpeper, VA, 22701

About: Hello, I have been taking care of a wide range of animals since I was 15. I’ve had 5 ferrets, guinea pigs, cats and dogs my whole life. I have a Staffordshire terrier, an American bully, and a black lab/ leopard catahoula mix. I am used to having a heavy dog on the opposite end of the leash and I am well experienced in animal body language to keep your baby and myself safe. I am an independent contractor who does Rover, Spark, DoorDash and a couple other side gigs. I have worked a 9-5 and it was incredibly difficult following a schedule someone else made for me while trying to manage my kids school and sports schedule's. Since becoming an independent contractor I have gained great relationships with residents of Culpeper and Rappahannock county and more time with my kids. These side gigs help provide me a way to bring in income, socalize, work easily with my kids school and sport schedules and give me the flexibility to rest when my autoimmune disease flares up. I will make sure any and all instructions are followed correctly to ensure adequate and safe service. Plus a few head rubs before I left.

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: Mireille H.
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Mireille H.
from
$75
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
40 years of experience
Stephenson, VA, 22656

“Mireille was great. I could tell right away that she had a genuine interest for our dogs and would be a good match for them. We have one who is older with several anxiety triggers and one who is younger and a handful and has a endless desire for cuddly attention. Mireille satisfied both their needs. She was also good with the communication and flexible when our return home was a bit delayed. Would recommend her highly.”

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Diane G.
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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

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

This was our first time booking with Selina. We had a meet and greet prior to the sitting time. And, we knew at that time that she was the sitter for us. During our time away, Selina kept us informed and sent pictures. She even had a sighting or two of one of our kitties who normally hides from the world when we are away. Selina cleaned up after the cats eating sessions and kept our flowers alive. All of our cats were very happy in Selina's care and we will be booking again. Thank you Selina!

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Tammie A.
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
1 / 1
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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

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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 September 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 September 2026, there are 773 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:

  • 91% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 93% 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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