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.
“Courtney was fantastic! She took great care of my dog, Max, followed all his care instructions, and provided photos and updates regularly. She also left my apartment spotless and was an extremely respectful house guest.”
“Beth is so caring and conscientious! Our home and dog were cared for like her own. We were away several days for our son’s wedding We couldn’t have asked for anyone better. We will definitely ask her again.”
“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.”
“Brittany was awesome for us and our two pups (one of whom is a bit slow to warm up to new people). Brittany was able to take care of our dogs exactly how they’re used to and was very communicative with us while we were away with messages and pictures! She even toughed out a big snowfall and made sure our pups were all set throughout it. Brittany treated our home with great respect and left things very neat, clean, and tidy. We will definitely be calling her when we need a sitter next!”
About: Living in the OBX, Willing to travel, see new places! I want to help care for your dog in your home because I believe pets are happiest in their home setting. I never boarded my dog, always traveled with him or had a family member stay. I'm excited to meet all your fur family and see some new places. If you live near trails, i particularly enjoy a hiking dog. I will travel for overnight care up to a few hours. I also visit NH regularly. Im working on something personal right now which allows me the flexibility to travel and dog sit. I prefer the beach, mountains, lakes, quiet over cities. I'm a kiteboarder and hiker, so i'm partial to areas I can explore with these activities. I always follow the household schedule and your pets preferences. During my time in your home, I will leave it generally cleaner than I found it. I'm comfortable traveling to dog parks, trails etc with a dog or two in my car.. I'm happy to keep your plants happy, enjoying a green thumb.
“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.”
“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!”
About: I have been with animals my whole life from bunnies to lizards and of course dogs and cats I currently have 2 dogs that are old one is 13 and the other is 11 and I have a bearded dragon who just turned 1 I am currently not working and while I am looking for a new job I have open availability for rover and o have no schedule I will be taking care of your animals in your home they will get all of the loving and play time they want we will go outside and play too if we can
“We were super anxious about leaving our dog and home but Liz made the experience as stress free as possible. We felt comfortable with here the moment she met us and Gizmo! She kept us updated with pictures of our dog and how he was doing throughout the day. I would recommend Liz to any one needing a house/pet sitter. ⭐️⭐️⭐️⭐️⭐️⭐️. Thank you Liz. You rock!”
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.
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!
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.
“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!”
The median cost per night for house sitting in Wintergreen is $36
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Wintergreen sitters!Sitters in Wintergreen average 3 repeat house sitting clients
FAQs for House Sitting - Wintergreen
Frequently asked questions about Rover
As of June 2026, there are 324 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
- 89% 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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