Dog Boarding Winesap
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Winesap, 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.
“I left my elderly dog with Brenda and am very pleased! This was my first time ever leaving her with someone I didn’t previously know, so I was nervous about it! Brenda, however, was awesome and took great care of her. She sent a lot of pictures and updates and stayed in communication with me consistently. I would definitely recommend her and use her again!”
“Emily and Donnie were amazing with Zeus! She made me feel comfortable and sent pictures while I was away on my trip in TN! I will definitely be using them again!”
“We used Casey for the second time to watch our three crazy, energetic dogs—and once again, she was absolutely amazing! Each of our pups has their own unique personality, and Casey handles them all with so much patience and love. She takes them on tons of walks, keeps them entertained, and always sends us lots of photos while we’re away, which we love and really appreciate. We honestly can’t recommend her enough!”
“Marketa and Jay took great care of our Trooper! We are happy to say that we have found a safe and loving family to care for our dog while we visit our son at Liberty U. We definitely recommend them to everyone.”
“Jessica did an excellent job caring for my dog Rupi. She took Rupi on long walks every day and sent pictures/updates regularly. I would highly recommend Jessica.”
“My husband and I have 100% confidence in Chantal. She always provides great updates, is very flexible around drop off and pick up times— which is especially important when a train or a flight is delayed — and our dogs are treated as if they are her own, with lots of snuggling and play time. We have no anxieties about them while we’re gone. Highly recommended!”
“Allison was an excellent communicator while coordinating our pup's day care and was absolutely flexible to help us with our out-of-towner schedule, and was wonderfully attentive to our pup during his stay. Great first experience using Rover - I would recommend Allison for anyone looking for a caring dogsitter!!”
“So grateful for Tiffany! She took wonderful care of our puppy for us and we had such a peace of mind knowing that she was loved on and cared for! We will be back!”
About: I’ve had dogs ever since I can remember. From a golden retriever, Chocolate lab, Chihuahua to an American Bulldog. We lost our Poe (American Bulldog) several months ago and instead of getting an new pup I want to love yours! I am active and will take your pup on walks and they will get the best care and attention while you’re gone. We have a doggie door so they can get out whenever they need to and be in our enclosed backyard. I currently work from home with lots of flexibility!! I might run to the gym or to the store but your pup will be covered. My husband and I are a team and love animals! We live on 11 acres. So plenty of space to roam with several fenced in kennel areas as well as wide open area to play and run.
“Jennifer did a fantastic job taking care of Bentley while I was on vacation. She kept me updated throughout the week and sent me pictures of him. He can be a timid dog so his immediate comfort level around Jennifer was so relieving! I would absolutely recommend Jennifer and will use her again when going away.”
“Maddie did an amazing job and sent regular photos and updates! It was a relief while I was out of town to know he was well taken care of and happy. She went above and beyond and I will definitely be contacting her again for future stays and walks!! :)”
About: I have taken care of animals since I was 10,family friends and neighbors have trusted me and I love animals I treat them just like big babys!! I have a dog of my own and also 3 ducks who we love dearly ❤️ we have a large yard for our animals to run around in. I love all types of animals❤️ I am a very well trusted person. I am 25 and I am married. I also who have a daughter is who is almost 3 and she is very much an animal lover too. I am also in school to become a teacher! Since I am going to school and am a stay at home mom I am pretty much available anytime ! I can also house animals in my home. I will do whatever request the owner ask! I love all animals all sizes. I have a lot of experience with animals. Growing up my family and I fostered and rehoused dogs all the time so I am pretty knowledgeable about animals and their needs.
The median cost per night for dog boarding in Winesap is $40
Dog parents share their Rover experiences - Winesap
Kasalyn was absolutely wonderful. She took great care of Addyson and Addyson had a great time. Kasalyn was very kind, made me feel comfortable and eased my mind about leaving my baby. She also send lots of awesome pictures and updates. Thanks for all you did Kasalyn😊
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 - Winesap
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winesap average 10 repeat dog boarding clients
FAQs for Dog Boarding - Winesap
Frequently asked questions about Rover
As of November 2026, there are 102 sitters on Rover offering Dog Boarding across Winesap. 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.
95% of sitters in Winesap 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 Winesap 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 Winesap.
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 Winesap. On Rover:
- 91% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 95% 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 Winesap 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.
Connect anywhere with the Rover app
