Hotel Dylan
320 Maverick Road
Woodstock, NY
Bohemian sophistication at the foot of Overlook Mountain
About Hotel Dylan
Hotel Dylan sits at the base of Overlook Mountain just outside the village of Woodstock, close enough to the town's music venues and shops to walk into its history. From the road it reads like a classic motel, low and drive-up, but the design tells a different story. The rooms were shaped by the Novogratz, a husband-and-wife design team known for a bohemian-sophisticated aesthetic, and the result is a stay that nods to the 1960s Woodstock spirit without turning it into costume. Vinyl records, curated books, and a warm, layered palette give the place a point of view that suits its town. It is a small, personal operation with kind, familiar staff, and it draws guests who return year after year for the vibe and the setting.
What Hotel Dylan Is Known For
Hotel Dylan pulls off something Woodstock properties often get wrong: it evokes the town's 1960s spirit through genuine design rather than theme-park nostalgia. The Novogratz hand gives every room a bohemian-sophisticated point of view, and the record players and vintage vinyl make the era feel lived-in rather than staged. Pair that with a heated saltwater pool, lawn fire pits, private outdoor entrances, and a setting at the base of Overlook Mountain, and it earns its standing as a genuine boutique retreat just outside one of the most storied small towns in America.
Amenities
- Pets Welcome
- Heated saltwater pool
- In-room record players with 1960s vinyl
- Two lawn fire pits
- Ping-pong table
- Hammock
- On-site Mexican restaurant (Santa Fe Woodstock)
- Curated in-room book collection
What Guests Love
- Every room has a record player and a stack of 1960s vinyl, so the Woodstock spirit is built right into the stay.
- The heated saltwater pool and two lawn fire pits give the central lawn a relaxed, social energy in season.
- Santa Fe Woodstock, an on-site restaurant serving traditional and modern Mexican cuisine, is steps from your door.
- Every room has its own outdoor private entrance, and some open onto a courtyard terrace.
- The village of Woodstock, with its shops and music venues, is a short drive away.
Worth Knowing
- Dog-friendly rooms are limited and must be reserved by phone rather than online. Call ahead to confirm availability before booking.
- Check-in is coordinated with the front desk, so call to let them know your arrival time.
- A two-night minimum applies on weekends, and the saltwater pool and fire pits are seasonal. Contact the property to confirm what will be available for your dates.
The Room
Each room carries the Novogratz signature: bohemian, layered, and considered, with color and texture doing the heavy lifting rather than clutter. A record player and a stack of vinyl albums from the 1960s sit in every room, an invitation to slow down and put something on. Curated books, quality LATHER bath products, an in-room coffee maker, a mini-refrigerator, and individual climate control round out the comforts. The rooms are spacious and comfortable, with modern bathrooms and beds that guests single out for a good night's sleep. Every room has its own outdoor private entrance, and some open onto a terrace facing the inner courtyard, giving the stay a quiet, self-contained feel.
The Grounds
The property is built around a central lawn, and that green heart is where the days unwind. A heated saltwater pool opens in the warm months, and two fire pits come alive on weekend evenings. A ping-pong table and a hammock give the lawn a loose, playful energy that fits the Woodstock spirit. Rooms open directly to the outdoors, with parking right at your door and Overlook Mountain rising behind. Santa Fe Woodstock, the on-site restaurant, serves traditional and modern Mexican cuisine just steps from your room.
The Experience
There is an easy, unhurried feel to a stay here. You put a record on in the afternoon, drift out to the lawn for a game of ping-pong or a float in the saltwater pool, then gather at a fire pit as the evening cools. Dinner is a few steps away at Santa Fe Woodstock, and the village and its music history are a short drive down the road. The staff are warm and genuinely welcoming, the kind who make guests want to come back, and many do. It is a place that captures the Woodstock spirit without leaning on nostalgia, and that balance is what keeps people returning.
Details
Woodstock, NY 12498
The Boutel designation is earned, not purchased. Boutels is editorially independent and has no financial relationship with any listed property.
Frequently Asked Questions
Does Hotel Dylan serve breakfast?
No, breakfast is not included at Hotel Dylan.
What is there to do near Hotel Dylan?
Woodstock Village: 3 miles, about a 5 minute drive, or you can bike there. Overlook Mountain: 5 miles, about a 10 minute drive, or you can bike there. Kaaterskill Falls: 20 miles, about a 40 minute drive.
How far is Hotel Dylan from Woodstock Village?
Woodstock Village is about 3 miles from Hotel Dylan, roughly a 5 minute drive or a short bike ride.
How far is Hotel Dylan from Overlook Mountain?
Overlook Mountain is about 5 miles from Hotel Dylan, roughly a 10 minute drive or a short bike ride.
How far is Hotel Dylan from Kaaterskill Falls?
Kaaterskill Falls is about 20 miles from Hotel Dylan, roughly a 40 minute drive.
Is Hotel Dylan pet friendly?
Yes. Hotel Dylan welcomes dogs in a limited number of rooms, which must be reserved by phone. A pet fee applies; contact the property directly to confirm current amounts and any restrictions before booking.
Does Hotel Dylan have a pool?
Yes. Hotel Dylan has a heated saltwater pool on the central lawn. It is seasonal, so confirm it will be open for your dates.
How far is Hotel Dylan from Woodstock Village?
The village of Woodstock is about 3 miles away, roughly a 10 minute drive from Hotel Dylan.
Does Hotel Dylan have a restaurant?
Yes. Santa Fe Woodstock, on the property, serves traditional and modern Mexican cuisine just steps from the rooms.
How does check-in work at Hotel Dylan?
Check-in is coordinated with the front desk. Call ahead to let them know your arrival time so the team can be ready for you.
Does Hotel Dylan have EV charging?
Hotel Dylan does not list on-site EV charging. Contact the property directly to ask about the nearest public charging options.
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Things to Do Near the Catskills
Overlook Mountain House ruins and fire tower
4.7 miles away
This is the Woodstock hike locals send you on. The trail is a steady two-mile climb up an old road to the haunting concrete shell of the Overlook Mountain House, a hotel that burned and was left to the forest, now covere...
Opus 40
4.8 miles away
Most people driving the Thruway have no idea this is tucked in the hills near Saugerties.
Platte Clove Preserve
9.2 miles away
A 208-acre Catskill Center wilderness preserve at the head of the rugged Platte Clove, with a short steep trail to plunging Plattekill Falls, a creek-side nature loop past 19th-century boarding-house ruins, and a king-po...
Montgomery Place
11 miles away
A Federal-era Hudson River estate and National Historic Landmark on nearly 380 acres, built by a general's widow and now part of Bard College's campus.
Esopus Creek
11 miles away
A storied Catskill trout stream that doubles as a beloved summer tubing river, curling right through the hamlet of Phoenicia along NY Route 28.
Empire State Railway Museum and Phoenicia
11 miles away
Phoenicia gives kids two things at once: trains and a river to float. At the old 1899 depot, the Empire State Railway Museum lets them climb around real locomotives and cars from the mountain railroad era, with hands-on...
Hunter Mountain Fire Tower
13 miles away
New York's highest fire tower, a restored 60-foot steel lookout on the second-highest peak in the Catskills at 4,040 feet.
Slide Mountain and the Catskill Park
13 miles away
Slide Mountain tops out at 4,180 feet, the highest point in the Catskills, and climbing it takes you through a compressed slice of northern wilderness.
Kaaterskill Falls
14 miles away
Kaaterskill Falls is the tallest cascade in New York, dropping 260 feet in two stages through a mossy amphitheater of Catskill sandstone.
Old Rhinebeck Aerodrome
14 miles away
Most people driving to Rhinebeck for the antiques never realize there is a squadron of flying World War I biplanes just out of town. The Old Rhinebeck Aerodrome does not just park its antique planes; it flies them.
Diamond Notch Falls
14 miles away
A twin cascade on the West Kill in the Catskill Forest Preserve, reached by an easy mile-long walk on the blue-blazed Diamond Notch Trail from the trailhead at the end of Spruceton Road, west of Hunter.
West Kill Mountain
14 miles away
West Kill Mountain is a forever-wild Catskill High Peak, the sixth highest in the range, rising at the head of the quiet Spruceton Valley.
Hunter Mountain and the Kaaterskill Rail Trail
15 miles away
For families, Hunter Mountain works in every season. In winter it is a full ski and snow-tubing hill with lessons for kids.
Mohonk Preserve and the Shawangunk Ridge
16 miles away
The Shawangunk Ridge is a geologic showpiece: a long wall of hard, pale Shawangunk conglomerate, quartz pebbles cemented in white sandstone, thrust up and tilted so its cliffs face the valley.
Minnewaska State Park Preserve
20 miles away
High on the white cliffs of the Shawangunk Ridge, Minnewaska holds rare turquoise sky lakes, waterfalls like Awosting Falls, and about 35 miles of gentle old carriage roads that make clifftop views easy walking for all a...
Woodstock Village
3 miles, about a 5 minute drive, or you can bike there.
3 miles, about a 10 minute drive, or you can bike there. The famous small town's walkable center is full of galleries, independent shops, live music, and restaurants steeped in 1960s history.