Where to Stay: A Guide to the Most Creative Hotels in the Catskills

Looking for a weekend getaway in Upstate NY or a staycation for a change of scenery? Immerse yourself in the creative energy of the Hudson Valley and Catskills by checking into some of the most thoughtfully designed boutique hotels in the Northeast. Whether you’re seeking fairy-tale drama perfect for cosplay, a vintage vibe from Victorian to the mod ’60s and ’70s, or bohemian luxury, there’s a perfect stay waiting for your arrival.  Take a peek at our hotel roundup below to choose your favorite artsy, chic hotels that combine style and comfort with an unexpected twist.

Featured: Creatively Chic Hotels Upstate NY

Twin Gables | Woodstock NY  |  @twingablesofwoodstock | INSIDE+OUT In the Spotlight

“A creative haven since 1926,” Twin Gables is an eclectic, design-centric, community-driven boutique hotel right in the heart of the vibrant village of Woodstock in Upstate New York, surrounded by the Catskills Mountains. ​Created by artists, for artists almost 100 years ago, and with its revival in 2019, it continues to serve the creative community and beyond. Photos: Katrina Zoe Norbom.

+ + +

MORE CREATIVELY CHIC HOTELS IN THE HUDSON VALLEY

The Herwood Inn | Woodstock NY |  @theherwoodinn

Located in the heart of Woodstock, NY, the Herwood Inn is dedicated to positive change. Their joyfully designed rooms pay tribute to Joni Mithchel, Stevie Nicks, Aretha Franklin, and Carol King in appreciation for the positive change created through their lives and music. The Herwood offers eco-friendly, cruelty-free, and fair-trade products to its guests, while providing a serene boutique experience just on the edge of Woodstock’s vibrant shopping and dining district.

+ + +

Hotel Dylan | Woodstock NY | @hoteldylan

Inspired by vintage vibes and the rich music history of the most famous small town in the U.S., Woodstock NY, mountain-chic Hotel Dylan offers photo-worthy moments and all your favorite amenities from start to finish. Designed by duo Cortney and Robert Novogratz, all of the Hotel Dylan rooms offer true bohemian sophistication, presenting an ambiance that parallels the easy, laid-back character of Woodstock and the locals who call it home. Each room is named after one of the rock n’ roll greats associated with the Woodstock Nation, and iconic artwork by Elliott Landy and Michael De Feo grace the walls.

+ + +

Hotel Tivoli | Tivoli NY | @hoteltivoli

Hotel Tivoli, together with its vibrant farm-to-table restaurant, The Corner, stands as a century-old gem in the historic Village of Tivoli, New York. Established by visionary painters Brice and Helen Marden, this remarkable property showcases an inspiring eclectic collection of furniture, lighting, and art.

+ + +

The Roxbury | Roxbury NY | @theroxburyexperience

The Roxbury is one you just must see for yourself. Named the most magical hotels in the world by Travel + Leisure, this is a genuine choose-your-own-adventure getaway, between the original Retro-chic Roxbury Motel, the new Roxbury Mansion, and the Signature Cottages experience at Stratton Falls. At the Motel, embrace the whimsy of themed design in rooms and suites crafted to spark the imagination. Just a short drive away from the Motel, you can immerse yourself in the magic of the Mansion and Crooked Cabana, complete with a cafe, pool, sauna, and hot tub. Escape to your own private wonderland in the enchanting cottages that will transport you on a cosmic adventure, to ancient Egypt or to a Faerie Forest (to name a few)–all with breathtaking views of Stratton Falls.

+ + +

The Six Bells Countryside Inn | Rosendale NY | @thesixbells

Discover a storybook world at this three-floor, eleven-room inn in the Hudson Valley. The Six Bells Countryside Inn, located in quaint and charming Rosendale, is designed with a love of country style. An expansion of The Six Bells, a country-inspired home goods company, this historic inn is thoughtfully curated to help you feel at home amidst pieces of the past, including canopy beds, archival wallpaper, and a color palette that straddles the line between pastels and melancholia. It’s “a storybook you can sleep in,” complete with a tavern, riverside restaurant, and shop.

+ + +

Starlite Motel | Kerhonkson NY | @thestarlitemotel

The Starlite Motel is for vintage-obsessed travelers. A lovingly restored 1960s motel with good vibes and max comfort at the foot of the Catskills, The Starlite Motel is just a short distance from Minnewaska State Park. When you’re done exploring the best hiking, biking, and climbing around, come back and relax in a hammock or by the fire. This motel also hosts a variety of on-premise events not to be missed!

+ + +

EXPLORE THE DIRECTORY for anything you’re looking for, whether you’re living, visiting, or working in the Hudson Valley!