Leaf Peeping at the Woodstock Barn | Bonfires, Pizza & Movie Nights | Apartment in Bearsville

Summary:
The Woodstock Barn is a beautifully restored 1889 gem featured in Vogue and “Woodstock Handmade Houses”—located just 8 minutes (current rd closure so may take longer) from the heart of Woodstock. The property embraces the property’s original 1800’s character with upgraded touches including a fully-fenced in-ground pool, 12-foot movie screen projector, and outdoor pizza oven. You will be situated at the foothills of the Catskills.
The Space:
What You’ll Love:
⎯▹ Backyard: Fenced in Pool, Fire Pit, Pizza Oven, Grill, Seasonal Outdoor Shower
⎯▹ Kid-Friendly: Fenced in Pool, Crib
⎯▹ Kitchen: Cooking Essentials, Dining Table for 12, Wet Bar
⎯▹ Cozy Spaces: Open Concept Living Space, Wood Stove
⎯▹ Media: Fast Wifi, 12’ Projector, Apple TV, Surround Sound
Location Highlights:
» Catskill Hiking Trails — Minutes Away
» Woodstock Downtown — 8 min drive (current road closure changes to 15 min drive)
» Ashokan Reservoir — 10 min drive
» Whitecliff Vineyard & Winery — 50 min drive
➤ R&R Local Tips: Once booked, you’ll receive our curated guide featuring favorite local eateries, hikes, and hidden gems.
Woodstock Barn Overview:
⎯▹ Bedroom 1: King Bed (main level)
⎯▹ Bedroom 2: Two Twin Beds (main level)
⎯▹ Loft 1 (Above Living Room): Full Bed with Privacy Curtain
⎯▹ Loft 2 (Above Kitchen): Full Bed (No Privacy Curtain)
⎯▹ Bathroom 1: Full Bath with Clawfoot Tub + Shower, Near Living Room
⎯▹ Bathroom 2: Full Bath with Tub + Shower, Near Kitchen
⎯▹ Bath Products Provided: Shampoo, Conditioner, Body Wash, Hand Soap, Lotion, Makeup Towels, Hand Towels
FAQs
➤Is the pool heated?
The pool is open from May-October (exact dates are weather dependent) and is NOT heated. The pool gets direct sunlight and is a refreshing experience during summer months. Pool towels are provided.
➤Are firewood and kitchen essentials provided?
Yes! Firewood for the fire pit, and all kitchen & bath products are supplied for your convenience.
➤Is the property air-conditioned?
No AC, but the historic barn stays naturally cool even on the hottest days.
♥ Meet Your Host
We are Root & Ramble — more than just managers, we’re placemakers cultivating experiences and places where groups can feel at home, unwind, and make memories.
The Root & Ramble Team will be here for you not only throughout your stay, but throughout your planning process. We’re here to help, so please do not hesitate to ask!
We’re honored to share this place with you and grateful to the homeowners for trusting in us. We cannot wait to welcome you to Woodstock Barn.
Your Hosts,
Root & Ramble Management
Guest Access:
Guests will have exclusive access to the entire Woodstock Barn, including the two private bedrooms, two expansive lofted sleeping quarters, chef's kitchen, and living areas. Enjoy the outdoor amenities, such as the fully-fenced in-ground pool (available from Memorial Day weekend to Labor Day weekend), the outdoor pizza oven, and the BBQ grill. Parking is available in designated spaces on the property. Please note that the garage is not accessible to guests. The fire pit is available for use, adhering to all safety instructions.
The Neighborhood:
Nestled in the charming Bearsville neighborhood, you'll find yourself surrounded by the beauty of the Catskills. Just a short drive away (approximately 8 minutes), the vibrant heart of Woodstock awaits, offering a delightful array of dining options, from cozy cafes to upscale restaurants. Explore unique shops and art galleries, immersing yourself in the town's creative spirit. For a taste of local culture, check out the Bearsville Theater, a renowned venue hosting concerts and events (a quick walk or drive). Nature enthusiasts will appreciate the proximity to hiking trails and outdoor adventures, making this location an ideal base for exploring the region's natural wonders.
Getting Around:
Getting around is a breeze from The Woodstock Barn. While a car is recommended to explore the Catskills, you'll find ample parking right on the property with designated spaces. For those flying in, the nearest airport is approximately a 1.5-hour drive away. Public transportation options are limited in this area, so planning your journey in advance is advised. Woodstock town center is just an 8-minute drive, offering a variety of shops, restaurants, and cultural attractions. Enjoy the peace of the countryside with easy access to local amenities.
Other Things to Note:
✔️ The Woodstock Barn is a historic property with unique character and charm. Given the nature of older structures and our wooded surroundings, it’s possible that a friendly critter or the occasional bug might find its way inside. We clean thoroughly—including just before your arrival—and always strive to create a spotless and welcoming environment. Thanks in advance for understanding the quirks that come with staying in a space with such unique history.
✔️ Events and parties are not permitted to maintain peace in our residential neighborhood.
✔️ Parking is available in designated spaces on the property. Please note that the garage is not accessible to guests. The fire pit is available for use, adhering to all safety instructions.
✔️ Note that none of the common areas nor bedrooms have air conditioning (the entire house is heated). But thats for a reason - we've received overwhelming feedback that the home stays cool enough even in the hottest summer days.
✔️ You’ll have full access to the entire property, with the exception of a small attached owner’s cabin. Rest assured, the owners will not be onsite during your stay, so you’ll enjoy complete privacy throughout your visit.
Interaction with Guests:
We're here to help make your stay at the Woodstock Barn memorable. We respect your privacy while also being available at any time. Access to the property is self guided so you will never have to physically interact with us. Reach out with any questions whatsoever!

Leaf Peeping at the Woodstock Barn | Bonfires, Pizza & Movie Nights is located in Bearsville. Leaf Peeping at the Woodstock Barn | Bonfires, Pizza & Movie Nights provides accommodation, featuring TV, Bedding/Linens, Barbecue/Outdoor Cooking, among other amenities. This Apartment features TV, Bedding/Linens, Barbecue/Outdoor Cooking, to make your stay a comfortable one.

Leaf Peeping at the Woodstock Barn | Bonfires, Pizza & Movie Nights has 4 Bedrooms , 2 Bathrooms, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Apartment because of the excellent services rendered by the owner or manager of this Apartment, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Apartment has a friendly neighborhood, and the Bearsville has interesting places to visit. If you want to learn more about the Apartment in Bearsville, such as places to visit and things to do nearby, you can check below to learn more.