House Sitting Wintergreen
Find a loving house sitter to watch over your pets and your home.
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.
“Brady doesn’t warm up to new people easily, so Amy had quite a challenge from the start. She was incredibly patient, and kept us updated with frequent pictures, which gave us peace of mind. She took Brady on several walks to help calm his nerves. I felt comfortable knowing Brady was in her care, and I’ve already booked Amy again in November. I highly recommend her to anyone looking for a reliable, caring, and experienced pet sitter.”
“Sarah was fantastic in every way. She came out pre booking to meet us and our two dogs, and after booking, easily accommodated our small schedule change, an additional day added. She has a lovely personality and a keen wit, and she lovingly cared for our two dogs and our home going above and beyond with daily check-ins and photos. We would definitely ask Sarah to sit for us again. We highly recommend Sarah and are grateful to have met her.”
“Dylan immediately understood our pets needs and required very little direction. He was very attentive during his week long booking and kept our pups very happy. I would highly recommend him and will definitely try booking him again in the future.”
About: I’ve taken care of many dogs in my life. I worked as a vet assistant and I’m now working towards a certification of vet assistant. I have one cat and one lizard. I had 12 dogs before and took care of them all. Ranged from chihuahuas to pit bulls. I’m currently working in the military. And I live animals very very much. I have a cat named Gray and a bearded dragon named Shmoop. I would have to go to clients house to care for the animals, as I live in apartments at the moment. I would need to know how owner does certain things for the animals.
“Hailey was an amazing sitter. The dogs loved her and she took great care of the house. She followed instructions and sent photos and videos throughout the days she was there. She was available for a short notice booking and made time to have a meet and greet.”
“John is awesome! My dog Bruno bonded with him immediately and he took great care of him, sending pics and updates every day. And I have to add…when I returned home, my house looked like no one had been there! HIGHLY RECOMMEND!”
“We usually have family take care of our dogs but being new to the area, we no longer have that option. We weren’t comfortable with leaving our dogs in a kennel so we found Laura. Not only was she affordable, but she came to our place so our dogs can stay where they are comfortable. Laura was great and we loved the updates and pictures. She was even able to accommodate another night stay when we decided to wait a day to come home. Will definitely be using her services again in the future.”
“Kiley was great!! Chloe loved her! When I arrived she met us downstairs—I was pressed for time! I dropped Chloe off with her “day bag” Gave Kiley a brief rundown on the “Belle “ and was off feeling that she was going to be well cared for!! She sent me pictures throughout the day it was great! Highly recommend— and I am neurotic—super picky about who I let care for my fur baby—who BYW is never left alone !”
“Hannah stayed in my home with my dog and cat while my husband and I were on vacation for a week. I have nothing but good things to say! Hannah was so sweet and took excellent care of my babies and my home! She was very communicative and sent me several updates per day. I trusted her with my babies and I could tell they were so happy and relaxed in her care! We will definitely work with her again in the future!”
About: I have been around all types of animals my whole life, especially dogs. I have house sitting experience and I have taken care of other people's animals previously just to help out. I’ve owned rats, and I’m no stranger to scaly friends if you have those as well. I have my own dog who is my best friend! My schedule is completely open right now because I do side gigs as needed. I’m hoping to eventually make this a long term full time gig! I love all animals and pet care is one of my passions. Any animal of yours I will treat like my own! I do not want you to have worry when you are away.
About: Hi there! I’m Z, and I’m a lifelong animal lover with a deep understanding of both cats and dogs. I’ve grown up with dogs and have a wonderful cat of my own. I also have years of experience caring for the pets of both my family and friends. Whether it’s playtime, cuddles, or ensuring your pet sticks to their routine, I treat every furry friend like they’re part of my own family. As someone who works part-time during the day, I have the flexibility to provide pet care in the mornings, evenings, and weekends. My schedule allows me to plan drop-in visits, walks, or playtime around your pet’s needs. Caring for animals is a natural part of my routine since I already care for my own cat. Whether it’s an early-morning visit before work or evening cuddles, I’m happy to adapt to ensure your pet feels loved and well cared for. When caring for pets in a client’s home, I focus on making them feel safe, loved, and happy in their familiar surroundings. I stick to their established routines, whether it’s feeding schedules, playtime, or walks, to keep things consistent and comforting for them. For dogs, that might mean exciting walks or outdoor play, while cats might prefer quiet companionship or engaging with their favorite toys. I make sure their environment stays clean and safe, and I’m happy to administer medications or meet any special needs. Along with meeting their physical needs, I give plenty of cuddles and attention to help them feel secure and loved. I treat every pet like part of my own family, ensuring they’re well cared for until their owner returns.
About: I provide dependable, attentive pet care with genuine compassion. I treat every pet like family, prioritize safety and comfort, and make sure owners feel confident and updated while away. I have walked/ stayed with many of my neighbors and family friends dogs all the time and have experience with taking care of their dogs as well as all 4 of my dogs I am free over the summer whenever anyone would need me for any type of care for their animals I am open too all types 7-days a week and open to however much time you want me too spend time with your pet/pets! In a client’s home, I respect both the pet’s routine and the owner’s space. I provide feeding, walks, playtime, medication if needed, litter box or waste cleanup, and regular companionship. I also send updates and photos so owners can feel reassured while they’re away. My goal is always to make pets feel safe, loved, and cared for like they are my own.
About: I personally have 3 dogs, 1 husky, 1 pittbull, and 1 chihuahua. I have had dogs growing up and have often dog sat for family and friends. I am a responsible 18 year old who just graduated from early college and am looking for jobs to keep me busy this summer. I am currently also working part-time so if I am given enough notice I work around my schedule to pet or house sit any day and time. When caring for clients animals I tend to give them a lot of attention and follow any rules given regarding feeding and/or house rules. When house sitting I tend to not mess with owners things and just keep to one space.
About: I genuinely love animals and treat every pet like royalty, even the dachshunds who judge from across the room! I’m big on play time, cuddles, walks and making sure your pet is comfortable while you’re away! I do currently work full time, but am remote 3 out of the 5 days a week making it easy to check in on your beloved pets at any time! My 7 year old lab, and 4 year old dachshund are treated not as pets, but as my children. They are literal humans if you ask me!
“We really loved Christine. Not only is she a kind, loving soul, she showed a lot of attention to detail. We felt comfortable leaving our babies with her and are planning on booking again! I have no reservations about her and she did a fantastic job!!!!! She is great!”
The median cost per night for house sitting in Wintergreen is $39
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. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
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 3 repeat house sitting clients
FAQs for House Sitting - Wintergreen
Frequently asked questions about Rover
As of August 2026, there are 323 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.
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 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 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 Wintergreen. On Rover:
- 95% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 90% 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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