House Sitting Wintergreen

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Wintergreen, 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: Shay M.
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Shay M.
from
$50
per night
22 years of experience
Afton, VA, 22920

About: I grew up with dogs, cats, goats, chickens, pigs, peacocks. You name it. I’ve been a huge fan of animals since I can remember. I’m super active outside and love taking pups out on hikes or walks. My last dog had to take meds so I’m also extra sensitive to pups that may need more present care. I’ve dog sat and house sat for many years before and just recently decided to give rover a try. I’m also a photographer so pics of your sweet pea will be guaranteed! I’m a photographer so my schedule varies. Sometimes I’m on a shoot or at home editing. I work part time at a restaurant wed-Friday so am unavailable those evenings. I am generous with my love with pets if they want that. If they are shy I will absolutely listen to what they need and let them warm up to me at their own pace. I am clean and respectful of others’ space and strive to make sure your sweet pup gets the activities they deserve.

Sitter Profile Image: Gretchen R.
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Gretchen R.
from
$30
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
50 years of experience
Nellysford, VA, 22958

“Gretchen is a gem found. She took great care of Kaiser and very easy to communicate and responsive. She also gave us lots of things to do around the region”

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Fion W.
Sitter Profile Image: Destiny L.
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Destiny L.
from
$35
per night
4.8 out of 5 stars
• 16 reviews
2 repeat clients
8 years of experience
Waynesboro, VA, 22980

“Destiny was absolutely wonderful! She is so kind, patient, and caring with the dogs, and I felt very comfortable knowing they were in great hands. Her communication was excellent, and she kept me updated throughout their stay.she kelpt our home very clean. I highly recommend Destiny to anyone looking for someone trustworthy and genuinely caring to watch their dogs. I will definitely book with her again! 🐾❤️”

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Alisa U.
Sitter Profile Image: Tyler C.
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Tyler C.
from
$175
per night
4.9 out of 5 stars
• 21 reviews
5 repeat clients
28 years of experience
Roseland, VA, 22967

“Tyler watched our crew of four in our home where they're all most comfortable. Everyone was in good spirits upon our return and our home was left very tidy. We'll definitely be reaching out for his help again!”

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Annie B.
Sitter Profile Image: Tiffanie F.
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Tiffanie F.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 27 reviews
7 repeat clients
30 years of experience
Waynesboro, VA, 22980

“Tiffanie was great. Even though last minute, she came to meet the dogs before her stay. She took great care of them, sent lots of pictures, was very communicative-commenting on each dog’s personality so you know that she’s spending time with them, and left our house in perfect condition.”

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Amy S.
Sitter Profile Image: Samantha K.
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Samantha K.
from
$175
per night
5.0 out of 5 stars
• 4 reviews
20 years of experience
Heards, VA, 22931

About: I am comfortable with all kinds of dogs and needs. I personally care for a GSD and a Heeler mix, and am comfortable with rambunctious and large dogs. Both of my dogs practice loose leash walking, and I love using our walks as time to tire their brains as well as their bodies. I can give medications, including subq and other injections. And I’m working on becoming a certified trainer, but for now I do not offer training services. I work a few part time gigs that change with the seasons. I have lots of flexibility to meet the needs of your pets. I generally do not go out of town during major holidays. I have lived on estates as a property manager, and ran my own home repair business for several years. I’m good at handling emergencies, and enjoy fixing things when I have the opportunity

Sitter Profile Image: Michael M.
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Michael M.
from
$47
per night
4.9 out of 5 stars
• 40 reviews
21 repeat clients
15 years of experience
Waynesboro, VA, 22980

“Michael was great with our dogs (one very high energy)! He was responsive and thorough even though I had limited cell service on our trip away. We will definitely book Michael again! Thank you!”

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Jennifer T.
Sitter Profile Image: Emma D.
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Emma D.
from
$32
per night
5.0 out of 5 stars
• 1 review
5 years of experience
Waynesboro, VA, 22980

“Emma did such a great job with our two pups! She sent plenty of updates and photos during her stay and we came home to a clean house and some happy dogs. I would definitely recommend her!”

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Marissa B.
Sitter Profile Image: Robert S.
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Robert S.
from
$27
per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
Staunton, VA, 24401

“Robert was great! He was very attentive to my pets. He responded promptly to any correspondence and engaged with both my cat and dog. I really appreciate the time he spent and the care he provided with both of my pets!”

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Katherine W.
Sitter Profile Image: Casey Y.
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Casey Y.
from
$45
per night
15 years of experience
Waynesboro, VA, 22980

About: I absolutely love animals and have had them through out my entire life. I have experience from working at “Dogtopia” to “Home away from home, dog boarding”. I understand the importance of family and would love to be your dogs next best friend! I have experience providing care for a variety of animals, including feeding, grooming, and monitoring health. I am familiar with cleaning and sanitizing animal housing and equipment, and can recognize signs of illness or distress. By feeding, walks, and playtime—with my personal habits like breakfast, exercise, and evening relaxation it helps to create a consistent, healthy routine. My successful routine with my 12 year old senior terrier includes early morning engagement to set a positive tone, scheduled midday breaks or mental stimulation to combat boredom, and structured evening bonding that eases stress. I have a 12 year old friendly Emotional support animal named Flower, who still loves to run and play. I also live close to the park, and have a crate if needed.

Sitter Profile Image: Olivia M.
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Olivia M.
from
$60
per night
10 years of experience
Scottsville, VA, 24590

About: What sets me apart is the level of love, patience, and personalized care I give every pet. I take the time to learn each pet’s routine, personality, and needs so they feel comfortable and safe while you’re away. I’m experienced with puppies who need consistency, potty breaks, playtime, and basic routine reinforcement, as well as senior pets who may need a gentler pace, extra patience, medication support, or additional comfort. I also provide regular updates and photos so pet parents always know their furry family members are happy and well cared for. I’m able to help out on Monday-Friday or Saturdays and Sundays. Let me know what fits your needs and I will be more then happy to accommodate! I focus on making pets feel safe, comfortable, and loved. Especially in their own home. I do not accept boarding as my currently home is renting.

Sitter Profile Image: Karleigh P.
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Karleigh P.
from
$95
per night
5.0 out of 5 stars
• 3 reviews
4 years of experience
Waynesboro, VA, 22980

“Great job by Karleigh. She was attentive and caring for our cat and dog and housesitting. She provided updates and ensured the house was well cared for. We would definitely use her services again.”

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Cape Z.
Sitter Profile Image: Mikayla C.
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Mikayla C.
from
$27
per night
20 years of experience
Waynesboro, VA, 22980

About: I have three dogs of myself and a rabbit! I’m previously from Arizona and I’ve had dogs for longer than I can remember. I have experience in taking care of elderly dogs (14+). Currently two of my dogs are with me in VA. I make sure to remove and sterilize shoes before entering the home. Just reach out and we can shot some time around and do a meet and great! Im a graduate student and my schedule is relatively free at the moment. Any type of changes to my schedule will be communicated. I can give more concrete times when given exact dates. I don't take pets in my home due to having two dogs myself. I make sure to sterilize shoes and hands before entering premises as a precaution for dogs with sensitive health.

Sitter Profile Image: Megan R.
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Megan R.
from
$80
per night
4.9 out of 5 stars
• 24 reviews
6 repeat clients
14 years of experience
Venable, Charlottesville, VA, 22903

“Megan was spectacular, stepping in with very short notice to dog sit my puppy for a week when my original sitter canceled a few days before I left. She took very good care of my dog a provided some very cute photos of the fun they were having”

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Matthew C.
Sitter Profile Image: Lindsay T.
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Lindsay T.
from
$55
per night
5.0 out of 5 stars
• 28 reviews
12 repeat clients
20 years of experience
Fry Springs, Charlottesville, VA, 22903

About: I have always had dogs in my life. My parents chose our first dog, a blue healer, after their honeymoon. I was three. Skeeter and I would tromp through the woods often. We moved to the Middle East when I was 9, and we had to give her to another family, but when we returned, we were contacted by the family: they were moving and wondered if we would like her back. It was a very happy reunion. She passed away when I was 18. In my third year of college, I decided to get a dog of my own. It was a dumb idea because I didn't have the forethought to think about how being a dogowner would limit my housing options over the next 10 years. Baloo was a German shepherd mix. He was a rescue from a Native American reservation in AZ, what we call a "res dog". He and I had several adventures over the decade I could call him mine. He passed away a little over two years ago, and I still miss him now. These days, I am mom to Benedict and Tigerlily. Benny is a sweet old rescue from California. He is likely part pitbull, and part sharpei. He's a sweetheart, super chill with my kids, and loves to walk the trails behind my house. Tigerlily Is a baby baby. The two of them are inseparable. I work from home and have my kids 3-5 nights / week. We love all the dogs and love to take them on walks through the woods and to the park. I provide a chill space where dogs feel like they can relax and trust that someone will come along soon to scritch their ears. I have a great neighborhood for walking and a large unfenced backyard.

Sitter Profile Image: Anastasiia & Mikhail G.
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Anastasiia & Mikhail G.
from
$40
per night
1 repeat client
10 years of experience
Charlottesville, VA, 22902

“Anastasiia and Mikhail were wonderful. We highly recommend them!”

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Chris W.
Sitter Profile Image: Dawn "Star" & Jonathan C.
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Dawn "Star" & Jonathan C.
from
$95
per night
4.9 out of 5 stars
• 129 reviews
41 repeat clients
30 years of experience
Charlottesville, VA, 22911

“Dawn was fabulous! She was communicative and really bonded with our dogs and ducks! She even left our house cleaner than she found it!!! I could not have asked for a better dog/duck/house sitter!”

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Zoe S.
Sitter Profile Image: Tina P.
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Tina P.
from
$60
per night
5.0 out of 5 stars
• 36 reviews
11 repeat clients
20 years of experience
Scottsville, VA, 24590

“Tina was wonderful with our puppy. He had never had a pet sitter before, and she took excellent and loving care of him, with lots of play time, exercise, and even some training. He even cried when she left! We will definitely ask her to take care of him again.”

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Carolyn C.
Sitter Profile Image: Crystal C.
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Crystal C.
from
$40
per night
4.6 out of 5 stars
• 21 reviews
5 repeat clients
20 years of experience
Lexington, VA, 24450

“Crystal took great care of our house and our dogs, and was a pleasure to work with, with really regular communication. We will definitely want her to come back.”

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Kirk L.
Sitter Profile Image: Casey L.
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Casey L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 128 reviews
50 repeat clients
11 years of experience
Amherst, VA, 24521

About: I know your pet is part of your family, & I truly consider it an honor to care for them. My goal is to keep them safe, comfortable, & happy while you're away. I homeschool my 3 kids, so I have a flexible schedule & spend a lot of time at home. That means your pet will get lots of attention, love, & care—not just a place to stay. I'm happy to follow their normal routine & will send regular photo updates so you know they're doing well. I also have experience caring for farm animals! I'd love to meet you & your pet. Feel free to reach out with any questions! 🐾 We have a flexible schedule & it allows me to provide plenty of attention & care throughout the day for your pet while you’re away. I treat every pet like they’re my own! I follow your instructions & your pet’s normal routine so they feel comfortable & cared for while you’re away. Whether they’re in my home or I’m caring for them in yours, I want you to have peace of mind knowing they’re safe & loved.

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

Pet parents share their Rover experiences - Wintergreen

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5.0 out of 5 stars

Gretchen is a gem found. She took great care of Kaiser and very easy to communicate and responsive. She also gave us lots of things to do around the region

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Fion W.
House Sitting
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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

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Wintergreen

Select a filter and find qualifying sitters offering house sitting.

Sitters in Wintergreen average 4
repeat house sitting clients

FAQs for House Sitting - Wintergreen

Frequently asked questions about Rover

As of October 2026, there are 434 sitters on Rover offering House Sitting across Wintergreen. 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 Wintergreen 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 Wintergreen 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.

<b>Tip:</b> 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 Wintergreen 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .

sitters on Rover set their own cancellation policy , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Wintergreen. On Rover:

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