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: 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: Sherry R.
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Sherry R.
from
$45
per night
4.9 out of 5 stars
12 reviews
6 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: 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 Izzy and left the house super clean.

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Becky J.
Sitter Profile Image: Gabriela G.
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Gabriela G.
from
$72
per night
5.0 out of 5 stars
32 reviews
10 repeat clients
13 years of experience
Manassas, VA, 20109

Gaby was great with my Brittany Spaniels and helped socialize my sometimes anti-social boy dog with her puppy!! She is very good with animals.

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Megan C.
Sitter Profile Image: Deborah G.
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Deborah G.
Star Sitter
from
$95
per night
5.0 out of 5 stars
69 reviews
20 repeat clients
40 years of experience
Woodbridge, VA, 22191

Deborah was amazing with our kitty! She provided loving care and kept us updated regularly on how she was eating, sleeping, and bonding. And we came home from our trip of 2+ weeks to a spotless house. We will definitely look to have Deborah sit again and would highly recommend her!

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Tammy B.
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
91 reviews
29 repeat clients
10 years of experience
Stephens City, VA, 22655

Megan was great. She kept us updated daily with the dogs. Made things stress free while we was gone. Will definitely be booking with her again in the future.

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Tyler M.
Sitter Profile Image: Hailey H.
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Hailey H.
from
$40
per night
5.0 out of 5 stars
2 reviews
1 repeat client
4 years of experience
Winchester, VA, 22603

Hailey survived our 3 dogs and we appreciated her care and attention. She stayed the whole day and everyone seemed content when we returned home. Would definitely ask her again!

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Rosie C.
Sitter Profile Image: Emelyn S.
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Emelyn S.
Star Sitter
from
$88
per night
5.0 out of 5 stars
57 reviews
17 repeat clients
3 years of experience
Purcellville, VA, 20132

Our little old man, who has seemed anxious after we've left him with some dog-sitters in the past, seemed calm and well cared for when we got home. Emelyn promptly sent an update every time I requested one and left our home very neat. She even emptied and refilled the dishwasher and watered the plants on the back porch. I would definitely recommend Emelyn!

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Lori G.
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
52 reviews
16 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: Courtney B.
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Courtney B.
from
$55
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
5 years of experience
Apple Mountain Lake, VA, 22642

Courtney is fantastic! She’s always on time, great at keeping in touch, and has tons of experience with dogs. She’s incredibly kind, and Millie adores her. During her stay of 3 nights and 4 days, she took excellent care of our home and left it just as she found it. We’re so grateful for the care she gave Millie and would recommend her to anyone!

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

Isabel is the best! My fur babies love her.

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Shay K.
Sitter Profile Image: Alyssa F.
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Alyssa F.
from
$50
per night
5.0 out of 5 stars
85 reviews
11 repeat clients
7 years of experience
Winchester, VA, 22601

Alyssa was an awesome sitter! My dog can be shy around new people and she did an amazing job getting my dog to warm up to her and she was excellent with sending updates and pictures! Will definitely use her again!!

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Jessica C.
Sitter Profile Image: Jai A.
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Jai A.
from
$25
per night
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Centreville, VA, 20120

About: Have only had 9 months total of my life without a dog or a pack of them by my side. Your fur baby will be fostered as one of my own; their walk, run, or potty break is all about them! With guidance from you, we will move at their pace. If they want to go for a run... then we run! If they prefer to walk tree to tree and smell every flower, that's fine too! I am available early mornings and mid-days during the week. I also have availability nightly to check on the pups and make sure they're ready for bed. I look forward to meeting the needs of your family, if it be walking or running the dogs, or making sure they are comfortable in your home, just let me know. I am fortunate enough to have a remote role, so my schedule is usually set to my own dog's needs. I am by no means a gym rat or a marathon runner. Yet that doesn't stop me from getting in usually 2-6 miles a day, both walking and running. While my dog is crate trained, it would be great if yours is as well, for those few errands that may take me away for up to 4 hours at a time (a busy week would be 3 half days in the office)

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: 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: Billy C.
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Billy C.
from
$40
per night
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Culpeper, VA, 22701

Billy was the perfect Dog Sitter. All four of my dogs loved him immediately. He took such good care of them. He was prompt, courteous, attentive to all of my dogs. He was fantastic, and I will certainly use him again.

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Lisa M.
Sitter Profile Image: Stephanie E.
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Stephanie E.
Star Sitter
from
$31
per night
5.0 out of 5 stars
18 reviews
4 repeat clients
20 years of experience
Fredericksburg, VA, 22406

About: I’ve taken care of dogs of every kind — from playful puppies to gentle seniors, and everything in between. I am the go to dog sitter for all my family and friends! Pet care fits naturally into my daily routine because I’m home most of the time and able to give pets plenty of attention, care, and supervision throughout the day. I treat every pet like part of the family! I make sure they feel safe, comfortable, and loved while in my care. I provide dependable care and regular updates!

Sitter Profile Image: Gabrielle F.
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Gabrielle F.
from
$40
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Haymarket, VA, 20169

Gabrielle did a wonderful job watching my my dog Henry and kept me up to date with messages and photos. Henry also seemed super happy and was very relaxed upon my return home which means he had great care and company. I would definitely recommend Gabrielle.

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Nick R.
Sitter Profile Image: Day B.
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Day B.
from
$60
per night
4.9 out of 5 stars
65 reviews
25 repeat clients
20 years of experience
Charles Town, WV, 25414

Absolutely fantastic experience with Day! Their communication was top-notch from start to finish, keeping us updated with photos and messages. Our dogs were incredibly happy and well-cared for, and it was clear they enjoyed their time with Day. We felt completely comfortable and at ease knowing our fur babies were in such good hands. Highly recommend!

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Elise W.
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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

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 August 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 August 2026, there are 806 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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