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
- WiFi
- 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, Hotel Dylan does not serve breakfast.
Does Hotel Dylan have WiFi?
Yes, Hotel Dylan has WiFi.
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?
3 miles, about a 5 minute drive, or you can bike there.
How far is Hotel Dylan from Overlook Mountain?
5 miles, about a 10 minute drive, or you can bike there.
How far is Hotel Dylan from Kaaterskill Falls?
20 miles, about 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
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.
Overlook Mountain
5 miles, about a 10 minute drive, or you can bike there.
5 miles, about a 15 minute drive. A rewarding hike leads to a 1927 fire tower and the ruins of an old mountain hotel, with sweeping views over the Hudson Valley.
Kaaterskill Falls
20 miles, about a 40 minute drive.
20 miles, about a 35 minute drive. One of the tallest and most photographed waterfalls in New York, a two-tiered cascade set in the heart of the Catskills.