Experience the charm of Woodstock, VA at On Cloud Wine a spacious, pet-friendly 19th-century gem just steps from history, restaurants, shops, cafes, and a movie theater. This 3 bedroom, 2.5 bath home features generous living space, a stylish bar room, full kitchen, and a remote work-ready office perfect for longer stays. Minutes from wineries, hiking, fishing, and Shenandoah River adventures. Comfort, character, and convenience all in one unforgettable getaway.
The space
Welcome to On Cloud Wine – A Historic, Pet-Friendly Getaway in the Heart of Woodstock, VA
Experience historic charm, modern comfort, and unbeatable location at On Cloud Wine, our beautifully restored 19th-century home in the very heart of downtown Woodstock. Thoughtfully designed for families, remote workers, groups, and even your furry friends, this spacious, pet-friendly retreat offers all the amenities you need for a rejuvenating stay in the Shenandoah Valley.
Room to Relax, Recharge, and Connect
Step inside and discover the perfect blend of historic character and modern comfort. Original details give the home a sense of timeless charm, while thoughtful updates ensure a cozy, convenient stay for groups, families, or friends traveling together.
* With three spacious bedrooms, everyone can enjoy a little something special—whether it’s mountain views, a
relaxing jetted tub, or a private balcony to sip your morning coffee or unwind under the stars.
* The 2.5 bathrooms are clean, roomy, and fully stocked with plush towels and essential toiletries, so you can pack
light and settle in with ease.
* The living room invites connection and downtime, featuring comfy seating for six, a large smart TV, and just the
right vibe for game night, movie marathons, or curling up with a good book.
Cook, Dine & Unwind in Style
Whether you're cooking, celebrating, or just enjoying time together, our shared spaces are designed to make your stay feel extra special:
* A fully stocked, renovated kitchen includes modern appliances, a spacious island with bar seating, and everything
you need to prepare a family meal or host a happy hour.
* The adjoining dining area features a charming birdcage-turned-wine-cabinet—just one of the home’s many
thoughtful touches.
* Head to the bar room to mix drinks, play ring toss or beanbag toss, or belt out your favorite tunes with our
karaoke machine!
Remote Work Ready
Need to catch up on work or school? Our quiet, dedicated office/library is designed for focus and productivity. Equipped with two external monitors, an ergonomic office chair, strong Wi-Fi, and USB charging options, it’s perfect for digital nomads or anyone working remotely.
Outdoor Living & Relaxation
Take in the crisp mountain air and small-town charm from any of our inviting outdoor spaces:
* Relax on the front porch with a cup of coffee and watch the world go by in our classic rocking chairs.
* Roast marshmallows and tell stories around the fire pit with seating for everyone.
* Let kids and pets roam free in the fenced backyard, or lounge in the sunshine on the quiet side porch.
Sleep in Comfort
Each of the three bedrooms offers its own unique charm—one features mountain views, another includes a private balcony, and a third offers a relaxing jetted tub. Whether you’re looking for a morning view, fresh air, or a spa-like soak, there’s a space tailored to your comfort. We provide luxury linens, plush towels, and high-quality mattresses to ensure restful nights and rejuvenating mornings.
Prime Location – Walk to Everything
Located just steps from downtown Woodstock’s restaurants, antique shops, cafes, movie theater, and historic sites, you’ll be immersed in local culture the moment you arrive. And when you're ready for adventure, you're just minutes from:
* Award-winning wineries and breweries
* Scenic hiking trails and waterfalls
* Fishing, tubing, and kayaking on the Shenandoah River
* The awe-inspiring Blue Ridge Mountains and state parks
Whether you're planning a romantic escape, a family vacation, or a get-together with friends, On Cloud Wine is your perfect home base to unwind, explore, and make lasting memories in the Shenandoah Valley.
We can’t wait to welcome you!
Guest access
The whole house and backyard areas.
Other things to note
* There is a town siren every day at noon - we call it the lunch bell.
* Some floors may feel uneven or spongy - we call it character.
* The original staircase inside is slightly crooked - we call it charm.
* Some door frame areas have a low height - both of us being under 6 ft, we call it a tall person problem... watch your head.
* All bedrooms and full bathrooms are located on the 2nd floor
We list the property as not suitable for infants due to the lack of safety features, not that they aren't welcome. The decision regarding children is entirely up to you. Please be aware that our 19th century home is not child-proof in any sense except for electrical covers.
