7 Stylish Long Island Stays with Old-School Charm and Modern Vibes

Admin
Jun 18
4 min read

Looking to escape for a weekend—or longer—on Long Island's North Fork or East End? These stunning properties offer the perfect mix of history, personality, and boutique-level charm. Once humble motels or Victorian homes, they’ve been thoughtfully transformed into unique destinations that still honor their roots.

Whether you’re craving peaceful beachside vibes, a luxury stay steeped in history, or a getaway with creative experiences, these seven stays should be on your Long Island bucket list.

🐚 Daunt’s Albatross – Montauk

📍 44 S Elmwood Ave, Montauk, NY🔗 dauntsalbatross.com💰 Rates vary seasonally

Just steps from the ocean, Daunt’s Albatross is a laid-back Montauk icon that’s welcomed guests since the ‘70s. This family-owned motel features 24 rooms that strike the perfect balance between vintage soul and coastal modern comfort—expect custom woodwork, vintage textiles, and natural stone floors.

Relax by the pool, grill dinner at the outdoor BBQs, or catch yoga classes and live music nearby. Guests can also head across the street to The Bird for cocktails and comfort food, or hop on a cruiser bike to explore Montauk’s natural beauty. Ideal for adventurers, families, and anyone who appreciates easygoing elegance.

🏖 Silver Sands Motel & Beach Bungalows – Greenport

📍 1400 Silvermere Rd, Greenport, NY🔗 silversandsmotel.com💰 Rates from $470/night

This retro-inspired gem features a mix of motel rooms, cozy beach bungalows, and two full beach houses, all steps from a private beach. Silver Sands nails vintage-meets-modern with playful touches like Nookies, a stylish on-site diner dishing up house-smoked fish, fluffy biscuits, and more.

Explore the area on a complimentary bike, take a guided oyster tour, or just unwind in your seaside room. It’s classic North Fork comfort, with just the right amount of flair.

🌄 Hotel Moraine – Greenport

📍 62005 County Rd 48, Greenport, NY🔗 hotelmoraine.com💰 Rates from $325/night

With sweeping views from atop a glacial ridge (called a moraine), this boutique hotel blends elevated design with laid-back vibes. Once the Sunset Motel, it’s now home to 20 polished rooms featuring fireplaces, terraces, and access to a heated saltwater pool.

Families love the ice cream socials and kid-friendly games, while adults can sip wine by the fire or head to nearby Croteaux Vineyards. The blend of relaxation and refinement makes Hotel Moraine ideal for couples and families alike.

🛎 The Lin Beach House – Greenport

📍 455 NY-25, Greenport, NY🔗 thelinbeachhouse.com💰 Boutique pricing; check website for availability

A beautifully restored Victorian in the heart of Greenport, The Lin Beach House is all about moody charm and curated experiences. Each of the six guest rooms features 17-foot ceilings, en suite baths, and chic touches like clawfoot tubs, brass fixtures, and (in some rooms) private balconies.

Guests can sip craft cocktails at Days Like These, the hotel’s cozy bar featuring spirits from the nearby Matchbook Distilling Co., or join creative events like “Create Your Own Gin” workshops. From seasonal dinners to local wine tastings, The Lin is for travelers who love design, culture, and a strong pour.

🌊 Aqua Beach Hotel – Aquebogue

📍 15 Bay Ave, Aquebogue, NY🔗 aquahotelbeachclub.com💰 Rates from $349/night

Once a quiet 18-room inn from the 1960s, Aqua Beach Hotel has blossomed into a serene, adults-only retreat right on the Peconic Bay. Expect total relaxation here—think beachside saunas, garden Jacuzzis, and in-room massages.

There’s no restaurant, but guests wake up to picnic baskets filled with breakfast bites, and a summer beach cabana serves wine, snacks, and charcuterie. You can also rent kayaks, paddleboards, or bikes to explore local farms and bayfront trails. Cozy, calm, and curated—Aqua Beach is made for dreamers.

🌅 Sound View – Greenport

📍 58775 County Rd 48, Greenport, NY🔗 soundviewgreenport.com💰 Rates from $500/night

Perched right above the Long Island Sound, Sound View feels like it's floating above the water—thanks to its elevated design and panoramic views. Originally opened in the 1950s, the hotel now offers 60 modern rooms with cedar-paneled interiors and private decks.

Guests can savor seafood and seasonal dishes at The Halyard restaurant or grab casual bites at Jack’s Shack. From piano bar nights to lazy afternoons on the beach, Sound View delivers that barefoot luxury vibe Greenport does best.

🏡 The Chequit Hotel – Shelter Island Heights

📍 23 Grand Ave, Shelter Island Heights, NY🔗 thechequit.com💰 Rates vary by season

Established in 1872 and recently revitalized, The Chequit Hotel blends historic charm with fresh, sophisticated design. Set in the heart of Shelter Island Heights, this boutique hotel offers 19 individually styled rooms with cozy finishes and modern comfort.

From its breezy patios to its curated boutique and seasonal events, The Chequit is perfect for slow mornings, coastal walks, and quiet evenings with a glass of wine. Enjoy farm-to-table meals at the on-site restaurant or unwind at The Tavern with local cocktails and small plates. With lush gardens and just steps from shops and beaches, it’s an idyllic island escape.