1 Block to Downtown | Historic 3BR Home

Entire home in Woodstock, Virginia

  1. 6 guests
  2. 3 bedrooms
  3. 3 beds
  4. 2.5 baths
Hosted by Scotty And Jenny
  1. Superhost
  2. 4 years hosting

Listing highlights

Top 5% of homes

This home is highly ranked based on ratings, reviews, and reliability.

1-hour drive to Shenandoah National Park

This home is near the national park.

Self check-in

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Stay in a beautifully restored 19th‑century home in the heart of downtown Woodstock. Just steps from restaurants, shops, and historic sites. This pet‑friendly 3BR, 2.5‑bath retreat sleeps 6 and is thoughtfully equipped with spacious living areas, a fully stocked kitchen, comfortable beds, fluffy towels, and a dedicated office with strong Wi‑Fi for workcations. Ideal for wedding weekends, family visits, or exploring the Shenandoah Valley’s wineries, trails, river, and mountain views.

The space
### Welcome to On Cloud Wine
*A Historic, Pet‑Friendly Home in the Heart of Downtown Woodstock*

Experience the charm of a beautifully restored 19th‑century home in the very heart of downtown Woodstock. Just steps from restaurants, antique shops, cafes, the movie theater, and historic sites, this spacious 3‑bedroom, 2.5‑bath retreat comfortably sleeps 6 and is thoughtfully equipped for families, wedding weekends, friend getaways, and workcations.

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## Room to Relax & Connect

Original architectural details blend seamlessly with modern comforts to create a space that feels both timeless and welcoming.

- Three spacious bedrooms offer something special for everyone—mountain views, a private balcony, or a relaxing jetted tub.
- Two full baths plus a half bath make mornings easy for groups.
- The living room features comfortable seating for six and a large smart TV—perfect for game nights or winding down together.

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## Cook, Gather & Celebrate

Whether you're making a family dinner or hosting a happy hour before a wedding, the shared spaces are designed for connection.

- A fully stocked, renovated kitchen with modern appliances and a large island with bar seating.
- A charming dining area with unique historic touches.
- A dedicated bar room with games and karaoke for a little extra fun.

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## Remote Work Ready

Need to blend work and travel? The quiet office/library includes two external monitors, an ergonomic chair, USB charging, and fast Wi‑Fi (565 Mbps), ideal for digital nomads or extended stays.

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## Outdoor Living

Enjoy small‑town charm and mountain air from:

- The classic front porch with rocking chairs
- A fire pit with seating for everyone
- A fenced backyard perfect for kids and pets
- A quiet side porch for morning coffee

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## Prime Location

Located just steps from downtown Woodstock’s restaurants and historic district, and minutes from:

- Award‑winning wineries and breweries
- Hiking trails and waterfalls
- Fishing, tubing, and kayaking on the Shenandoah River
- Shenandoah National Park (about 1 hour away)

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Whether you're visiting family, attending a wedding, exploring the Shenandoah Valley, or settling in for a workcation, On Cloud Wine offers comfort, character, and convenience in one unforgettable stay.

We can’t wait to welcome you.

Guest access
The whole house and backyard areas.

Other things to note
- The town siren sounds every day at noon — we call it the lunch bell.
- Some floors may feel uneven or a little spongy — we call it character.
- The original staircase is slightly crooked — we call it charm.
- Some door frames are a bit low — at under 6 ft ourselves, we call it a tall‑person problem… please watch your head.
- All bedrooms and full bathrooms are located on the second floor (stairs required).

We list the property as not suitable for infants due to the lack of safety features not because they aren’t welcome. The decision regarding children is entirely up to you. Please note that, like many 19th‑century homes, it is not child‑proof beyond standard electrical covers.

Where you’ll sleep

1 of 2 pages

What this place offers

Mountain view
Kitchen
Fast wifi – 565 Mbps
Dedicated workspace
Free parking on premises

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Rated 4.98 out of 5 from 133 reviews.

Guest favorite
This home is in the top 5% of eligible listings based on ratings, reviews, and reliability
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Overall rating

  1. 5 stars, 98% of reviews
  2. 4 stars, 2% of reviews
  3. 3 stars, 0% of reviews
  4. 2 stars, 0% of reviews
  5. 1 stars, 0% of reviews

Rated 4.9 out of 5 stars for cleanliness

Rated 5.0 out of 5 stars for accuracy

Rated 5.0 out of 5 stars for check-in

Rated 5.0 out of 5 stars for communication

Rated 4.9 out of 5 stars for location

Rated 4.9 out of 5 stars for value

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Where you’ll be

Woodstock, Virginia, United States
This listing's location is verified.

Neighborhood highlights

Historic Woodstock, VA is a great place to visit for several reasons, and staying in an 1880s home on Airbnb can be a unique and memorable experience for travelers. Here are a few reasons why:

Rich history: Woodstock has a rich history dating back to colonial times, and the town's historic district features a variety of well-preserved 19th-century buildings and architecture. You could take a walking tour of the town to learn more about its history.

Scenic beauty: Located in the heart of the Shenandoah Valley, Woodstock is surrounded by breathtaking natural scenery, including the nearby Shenandoah National Park and the George Washington National Forest. Visitors can enjoy hiking, fishing, and other outdoor activities, as well as taking scenic drives through the area's picturesque countryside.

Cultural attractions: In addition to its historical sites, Woodstock also boasts a variety of cultural attractions, including museums, art galleries, and performing arts venues. Visitors can take in a show at the historic Theatre Shenandoah or explore the Woodstock Museum of Shenandoah County.

Quaint charm: With its charming downtown area, friendly locals, and small-town vibe, Woodstock is a great place to escape the hustle and bustle of city life and enjoy a slower pace. Staying in a home built in the 1880s can add to the experience, allowing you to immerse yourself in the town's unique history and architecture.

Overall, Woodstock, VA offers a combination of history, natural beauty, and small-town charm that can make for a memorable vacation, and staying in an home built in the 1880s can provide a unique and authentic way to experience it all.

Meet your host

Superhost
133 reviews
4.98 out of 5 average rating
4 years of hosting
My work: Travel Agent & IT
I spend too much time: Watching TV

Scotty And Jenny is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.

Host details

Response rate: 100%
Responds within an hour
To help protect your payment, always use Airbnb to send money and communicate with hosts.

Things to know

Cancellation policy
House rules
Check-in after 3:00 PM
Checkout before 11:00 AM
6 guests maximum
Safety & property
Carbon monoxide alarm
Smoke alarm
Not suitable for infants (under 2 years)