5 Best Stays for Music Lovers in Upstate New York

Whether you’re a jazz hound or a country music fan, looking to stage dive into the hardcore punk scene, or fancy rekindling the spirit of Woodstock 1969—Upstate New York has a musical legacy to rival the best. From touring hotspots like Albany and Hudson to pioneering arts hubs like Narrowsburg and Woodstock, there’s live music playing somewhere every night of the week.

These five stylish stays will spark your creativity, get your toes tapping, and fire up your musical ambitions. Not only that, but each one makes an ideal basecamp from which to discover the Upstate music scene. Snag tickets to a summer music festival, check out the talent at a local bar, or follow in the footsteps of a musical legend. Here are our 5 best stays for music lovers in Upstate New York.

#1 Hotel Dylan

320 Maverick Road, Woodstock, NY 12498

Hotel Dylan: A Boutique Hotel in Woodstock New York

$150-400 per night

Hotel Dylan is the ultimate pitstop for bohemian road trippers looking to trade in their VW campervan for something decidedly chicer. Tucked in the foothills of Overlook Mountain and just a five-minute drive from downtown Woodstock, this boutique hotel is inspired by the town’s namesake festival (fact check: the festival itself was actually held in Bethel).

Each room is individually curated by design duo Robert and Cortney Novogratz with charmingly boho décor (think textured rugs and ‘Love is all you need’ throw pillows), retro touches (funky print wallpapers and Smeg mini-fridges), and a dash of rock ‘n’ roll (paintings of rock legends and Crosley record players paired with a selection of vinyl records).

On the guestlist: Rock star travelers looking to relive music’s glory days.

Your travel playlist: Hang out in the cafés and art galleries of Downtown Woodstock, pick up some Woodstock memorabilia along Tinker Street, then watch a gig at The Bearsville Theater or Levon Helm Studios. Or, indulge your inner hippie with a hike up Overlook Mountain and join a meditation class at Karma Triyana Dharmachakra Monastery.

#2 Rivertown Lodge

731 Warren Street, Hudson, NY 12534


$229-450 per night

Hudson’s musical heritage runs deep. Just 40 minutes from Woodstock, it’s also a major cultural hub with live music almost every night of the week, and Rivertown Lodge might just be the coolest place for music fans to sleep post-show.

Housed in a former 1920’s movie theater and decked out by Hudson artisans, the 27 boutique rooms boast cherry wood furniture and Scandinavian-inspired design touches. Borrow one of the Papillionaire bikes to get around town, cozy up by the wood-burning stove to read a book, and nurse your hangover over brunch at the on-site Tavern restaurant. Bonus points? There’s artwork on display by former Hole/Smashing Pumpkins’ bassist (and Hudson resident) Melissa Auf der Mer.

On the guestlist: Weekending New Yorkers who want to check out the Hudson Valley music

Your travel playlist: Swing by Club Helsinki, where live shows range from bluegrass to indie; attend a pop, jazz, or classical concert at Hudson Hall; or look out for events at Auf der Mer’s Hudson Basilica. If that’s not enough, head north to check out the music scene in nearby Albany.

#3 Outlier Inn

Woodridge, NY 12789


$170-529 per night

“Rest, Relaxation, and Rock & Roll” is the tagline at this 12-acre Catskills retreat, but it could equally be #glampinggoals. After all, where else can you sleep in a geodesic dome or tiny house amid rambling woodlands (cottages and bungalows are available too), with its own swimming pond, organic farm, and herd of goats and alpacas?

Where’s the rock & roll, you ask? Not only is this glamping getaway ideally situated for exploring Bethel (the afore-mentioned site of Woodstock festival), but it’s also home to two state-of-the-art recording studios (including a vintage Neve console and Otari tape machines). The likes of Bleachers, Damien Rice, and Blonde Redhead have all laid down tracks here, so you might find yourselves in the company of indie superstars.

On the guestlist: Audio geeks, roaming musicians, and their entourage.

Your travel playlist: Discover the history of Woodstock at the Bethel Woods Performing Arts Center (a 30-minute drive), check out the vintage guitar pedals at Steve’s Music Center in nearby Rock Hill, or put your headphones in and head into the woods to hike, fish, and get inspired.

#4 The Herwood Inn

148 Tinker St Woodstock, NY 12498
$330-550 per night

The second contender for Woodstock’s most rock ‘n’ roll hotel crown takes its free-spirited 1960’s aesthetic to a new level. Each of the four rooms has its own muse, so you can pick your musical icon: Carole King (The King Suite), Stevie Nicks (The Nicks Nook), Aretha Franklin (The Franklin Flat), or Joni Mitchell (The Mitchell Manor).

Each room is unique, with retro furniture, curated vinyl collections, and pops of rainbow colors, while the cedar hot tub and communal lounge area are ideal for mingling with other musos. You’ll even have your own kitchenette and private patio, making it a true home-away-from-home (if only your own home was this cool). There’s a two-night minimum for bookings, but you’ll want to stay much longer.

On the guestlist: Modern-day hippies who want to channel their inner Stevie Nicks.

Your travel playlist: Summer guest? Hop on a bike (provided) to explore Downtown Woodstock. Winter guest? Grab a sled (provided) and hit the slopes at Woodstock Sled Hill.

#5 Moonriver Inn

240 Bridge Street, Narrowsburg, NY
$260-475 per night

Housed in a mid-19th-century farmhouse—one of Narrowsburg’s oldest buildings—with idyllic gardens that look out over Delaware riverside, Moonriver Inn is the perfect marriage of chic and shabby. There are just four rooms to choose from, and the charm is in the details: an antique fainting couch, clawfoot bathtubs, turntables with a selection of old vinyl records.

It’s just a short stroll from Main Street Narrowsburg’s buzzing central drag, where you can explore the cafés, boutiques, and bookstores, then head back to the hotel after dark to enjoy some s’mores around the backyard fire pit.

On the guestlist: Culture vultures who are always on the hunt for the next big thing.

Your travel playlist: Attend the annual Riverfest street festival hosted by the Delaware Valley Arts Alliance each summer. Watch some live music at The Emerald Ballroom, enjoy a farm-to-table Sunday brunch with a view at The Heron, and visit the One Grand bookstore, where bookshelves are curated by artists such as Rufus Wainwright.


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