Dog Boarding Wintergreen
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Wintergreen, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Kathryn was great with our 7 month old cavalier mix. You can tell she loves what she does & I immediately felt safe leaving her. I highly recommend her & will be using her going forward for any overnight stays in the future!”
“Hillary was very communicative, flexible, and friendly. She was very attentive to our feeding/medicine instructions and communicated with me about what would be best. She did so much to help our dog, Marty, settle in. Marty came home happy and exhausted.”
“I’m thankful to come across Lissette and her wonderful family! They stole my heart on our meet and greet and Bella was such a fan! She immediately became comfortable and showed her true colors as being bossy and the ring leader. Lissette shared updates throughout the day, without having to ask which brought such a measure of peace. I would highly recommend Lissette and will continue to use her in all my future bookings.”
“Casey is amazing. It was our first time leaving our dog with anyone and we were delighted to see her on daily walks and sleeping soundly under her Christmas tree. She took the time to get to know Luna and sent daily updates on how she was doing/feeling. Casey was also very flexible and understanding. We couldn’t have asked for a better experience. Thank you so much!”
“Alexandra and Logan were wonderful with my (sometimes overly) curious terrier, Eddie! I am always concerned about Eddie escaping to chase an animal, and they took my concerns seriously and took steps to ensure that wouldn't happen. Their fence setup was great too - the fenced-in yard wraps all the way around the house, so even if a dog slipped out of the house, they would still be in the yard. On top of that, they sent lots of pictures and were so kind to Eddie. He didn't want to leave!”
“I am incredibly thankful to have discovered Joe! As someone who travels frequently, finding quality care for my dog can be an overwhelming experience. After some research, I decided to give Rover a try and stumbled upon Joe's profile. After reading the glowing reviews, I reached out to him, and I'm so glad I did! From the moment I contacted Joe, he was warm, friendly, and had a great sense of humor that immediately put me at ease. I ended up booking a four-day stay for my dog, Elsa, and it turned out to be a fantastic decision. Ironically, I found out that a friend of mine also knew him, which made me feel even more comfortable. When I picked up Elsa after her stay, I was amazed by how relaxed and happy she was. Typically, she can be anxious after a change in environment, but this time was different. She was bright, cheerful, and completely stress-free. In fact, when I dropped her off, she seemed so comfortable with Joe that she didn’t even notice I was gone! I've already scheduled more time for Elsa with Joe, and I can confidently say he will be my go-to caregiver from now on. If you're looking for someone who genuinely cares and creates a loving environment for your pets, Joe is the one! Highly recommended!”
“Cory did an excellent job, start to finish. He communicated in a timely and clear manner, was flexible, and sent pictures of our pup every day. Our dog came home happy and exhausted! We will definitely book with Cory again!”
“Jenny was great! This was our first time leaving our dog at someone else’s house for the weekend and I couldn’t be happier than having him stay with Jenny! She was very on top of responding to messages and sent plenty of pictures while we were away. Our dog has not yet learned to be off leash, so she had a great idea to let him roam around and play in the closed off barn with the other dogs. He came super happy and worn out. I highly recommend Jenny!”
“Ruby was excited and enjoyed staying with Madison. She did not appear to be at all anxious when we dropped her off, or when we picked her up. Often Ruby is initially uncomfortable and worried during her first stay, but that was not the case. We will definitely schedule her stay with Madison in the future!”
“Reyna is such a great host, she really made it feel like a home away from home for my sweet girl! She sent updates consistently, and I even got a puppy report card letting me know how my pup did during her stay (A+!!) I would very much recommend booking with Reyna, as she will fulfill all of your pups needs to a T!!! Thank you Reyna!!”
“Rylee was welcomed and taken great care of. Leaving her with others is a big deal for us, Arie, Leigh and the kids took great care of her. They sent us pics and updates over the weekend, we felt very safe with her there.”
“Erin took such great care of Honey. Friendly family. Accepting and fun furries of her own that might just turn into best 4-legged friends. We will definitely be repeat customers. Thank you Erin!”
“Emil is so helpful when I had to leave Rio for a business trip. He nicely accommodates Rio’s need and Rio is very comfortable under his care. I would not be hesitate to ask help from Emil again for my next business trip.”
About: I’ve had dogs and cats my entire life, so caring for animals has always been a big part of who I am! I have experience with pets of all ages, sizes, and breeds, and I’m happy to help with walking, playing, feeding, brushing, and providing plenty of love and attention. I also have experience administering various types of pet medications, including oral, topical, and ear medications. I’m comfortable following your pet’s specific care routine to help them feel safe, happy, and comfortable while you’re away. In addition to caring for my own pets, I’ve helped care for the furry family members of friends, relatives, and neighbors. I understand that every pet has their own personality and needs, and I’ll do my best to make sure your pets receive the same patience, love, and care I’d want for my own. I can’t wait to meet your furry family members! 🐶🐱❤️ I am currently a full time nursing student, but have availability pretty much anytime after 3pm throughout the week besides Saturday! Please feel free to message if you have any questions! My home offers a calm, low-stimulation environment in a cozy apartment with one resident cat, providing a peaceful space for pets who are comfortable around other cats. When caring for pets in a client’s home, my priority is to respect their home, follow their preferences, and maintain their pets’ established routines. I strive to make the experience as stress-free as possible for both pets and owners by providing attentive, reliable care and ensuring each pet’s needs are met efficiently and thoughtfully.
About: I'm very familiar with the whelping process, having successfully assisted several mothers through labor and delivery. I have extensive experience training and raising puppies all the way from eight weeks old into well-behaved adults. Even though I have a part-time job, my hours are incredibly flexible. I am ready to help starting at 6:00 AM, but I am not strictly limited to the mornings. I am fully open for daytime watching, evening care, or overnight boarding, ensuring your dog gets attentive supervision whenever they need it. I offer a secure, pet-friendly environment with a fully fenced yard where dogs can safely play. I have one friendly resident pet to keep your fur baby company, and I am highly experienced in managing introductions properly. Because of my background in whelping, puppy training, and full-lifecycle care, I prioritize constant supervision, follow your exact feeding routines, and can easily provide crate training or separate spaces if your pet prefers their own quiet time.
About: I have my associates degree in animal sciences and have been tending to animals of all kinds since I was very young. I have experience with farms along with typical house pets. I am a stay at home mom who loves to spend her days loving on animals and enjoying nature. We go on walks and enjoy each others company! I have 1 dog at home, which can be kept separate from other pets. I have an indoor/ outdoor cat. I have an extra large crate for those in need. I have a spacious yard, and leashes for those who need them.
“Thank you so much for taking care of Luna! You took wonderful care of her. Will definitely have her take care of my dog again. Loved that she sent pictures all the time so I could see how Luna was doing. Thanks so much!”
About: Hello, I am excited to meet you and your pup. I have worked professionally in clinic and in behavior for the last 21 years. I am a positive reinforcement based trainer for Good Pup. I have 3 personal fur babies and I foster with Save Rocky The Great Dane Rescue. I am currently working part time time so I have time in my schedule to devote to your fur kids. I have a doggie door for the emergency potties and I enjoy training so that can be part of the routine. I have a fenced in yard and I am able to provide mental enrichment as well as physical walks/Sniffari adventures and I have personal pups to keeps your busy! I have the ability to crate and even do drop bys at your house if needed.
About: Hi! I’m Julia a dedicated pet caregiver. I ensure to give your pet a safe and happy companion. I have had pets my whole life, and I love animals with passion. I’m sure I’ll love your furry friend. I just got back on River whilst I’m living at home and would love to gain more clientele. My shedule is very flexible. I will have uniterripted time to ensure your pet receives the care and attention they need. Your pet will be my number one priority. I have experience in creating a safe, happy, nourishing and loving environment for animals. I have taken care of dogs, cats, fish, etc and I’m committed to accommodating to their needs. I can provide watering and food bowls for your pet. I love being in nature, and can be sure to give your pet right amount of excercise. I hope to meet your furry friend soon and I excited to work together to give your pet the best care. My current schedule is very flexible. I will be able to give your all your animals the around the clock care they need Monday-Sunday! I have one dog. I spend a-lot of time with him each day. He is loved and cared for deeply. If your pet will be staying in my home we will need to discuss their relationships with other dogs to ensure they are in a comfortable environment.
The median cost per night for dog boarding in Wintergreen is $49
Dog parents share their Rover experiences - Wintergreen
Gretchen was incredibly responsive, supportive, & communicative — especially for a last-minute request. If I’m in the area again and need a dog sitter, I will definitely reach out; the care from her community of neighbors was incredible! I particularly appreciated their transparency & consideration for Bugs’ needs.
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 to book dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
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 dog boarding - Wintergreen
Select a filter and find qualifying sitters offering dog boarding.Sitters in Wintergreen average 10 repeat dog boarding clients
FAQs for Dog Boarding - Wintergreen
Frequently asked questions about Rover
As of November 2026, there are 199 sitters on Rover offering Dog Boarding across Wintergreen. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
97% of sitters in Wintergreen can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Wintergreen home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Wintergreen.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
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
- 96% can help with giving oral medications or injections
- 97% 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.
You and your Wintergreen sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
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.
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in VA ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
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 dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog 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.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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