The Hamptons is a string of seaside communities on Long Island’s South Fork that’s a popular getaway for affluent NYC residents. Its long stretches of white sandy beaches are lined with high-end restaurants, trendy bars, designer boutiques, upscale homes, and cool and unusual hotels.
While many visitors are wealthy, a mix of ages and income brackets come to the East End to party, relax, and enjoy water sports such as surfing, paddle boarding, and water skiing. To make your break even more special, from boutique inns to quirky and chic vacation rentals, here are the best cool and unusual hotels in the Hamptons (in no particular order, they’re all awesome…).
1. The Montauk Beach House- a boho-chic beachside hotel perfect for parties and watersports
Nestled in the heart of downtown Montauk, the Montauk Beach House offers an ideal location to experience the Atlantic Ocean and enjoy proximity to the area’s finest restaurants, bars, boutiques, and surf beaches.
The Montauk Beach House combines a free-spirited East Coast ambiance with a sprawling beachside setting, scrumptious food, and an action-packed social scene.
Travelers can choose their room from five different types of accommodations: the Moonlight Rooms, Whitewater Lofts, Whitewater Garden, Oceanmist/Terrace, and the Bungalow.
The beach house is famous for its weekend soirees featuring local DJs and endless rounds of flavorful cocktails. The onsite Bar & Grill offers an extensive menu for breakfast, lunch, and dinner.
To book, check prices or availability for the Montauk Beach House.
2. Baron’s Cove – an elegant, upscale, boutique-style hotel combining contemporary interiors with historic features
The resort pays tribute to the eclectic and artistic community of Sag Harbor, blending the community’s cultural heritage and nautical setting cleverly into the interiors and decorations.
Guests can choose from 67 tastefully decorated guest rooms, lofted suites, village rooms, and canine-friendly rooms. The rooms, lofts, and suites offer sprawling views of the vibrant village and picturesque harbors.
The iconic village rooms are ideal for travelers and honeymooners hoping for intimacy with their own private gardens.
To book, check prices or availability for Baron’s Cove.
3. American Beech Hotel- a fun, funky, and hip hotel perfect for partying Millennials and Gen Zs
Nestled in the heart of the iconic Stirling Square, the American Beech Hotel is the ultimate residence to live, work, play, and shop while enjoying the best of Long Island and the Great Peconic Bay.
Guests can choose their accommodation from a wide range of luxury deluxe apartments, king-sized suites, petite suites, and the sprawling bridal suite that’s ideal for newlyweds and honeymooners.
The American Beech is one of the best boutique hotels in the area, famous not only for its lavish suites but also for its hip social scene, in-house fashion boutique, onsite All-American restaurant, and the action-packed Black Llama, a cocktail and oyster bar.
The cool bar also serves as a venue to host private parties, post-wedding cocktails, and corporate events.
To book, check prices or availability for the American Beech Hotel
4. The Maidstone Hotel- an elegant, upscale historical hotel with spa-themed guest rooms and lavish amenities
One of the most trendy hotels in East Hampton, the Maidstone has an iconic legacy of serving jet-setters and travelers vacationing in the area since the roaring 20s.
Recently, the fun and trendy party hotel in The Hamptons has undergone a dramatic transformation, turning the interiors into a museum of opulence, fine art, and photography.
The guest rooms at the Maidstone are designed with a spa-like ambiance and a focus on aromatherapy.
Guests have access to an array of lavish amenities, including luxury Hastens beds, high-end Frette linen, organic toiletries, aromatherapy burners, free WiFi, Tivoli Bluetooth radio/speakers, and well-stocked minibars.
The cool hotel’s onsite restaurant, the Americana, is one of the best fine dining establishments on Long Island, serving traditional American recipes with seasonal flavors.
To book, check prices or availability for the Maidstone Hotel.
5. Haven Montauk- a chic and secluded retreat with exclusive bay access that’s perfect for watersports enthusiasts
Nestled against a picturesque backdrop of the harbor, this boutique hotel offers access to a private and secluded bay beach.
Haven offers 27 refined and modern guest rooms decked with innumerable amenities, appliances, and utilities to deliver home-like comforts with 5-star opulence.
Some of the best beaches in the area are tucked in the Haven’s backyard, making it ideal for surfers, ocean lovers, and water sports enthusiasts.
Guests can relax by the poolside or jump aboard the hotel’s complimentary bicycles to explore the breathtaking scenery of Montauk.
To book, check prices or availability for the Haven Montauk.
6. Hamlet Inn- a rustic-chic retreat ideal for an intimate sun and surf break
The hotel offers cozy and elegantly decorated bedrooms with a variety of accommodations designed for solo travelers, couples, families, and large groups.
The rooms and suites have an infectiously warm countryside appeal, decked with modern appliances, tasteful furniture, and comfortable sleep stations.
The Hamlet Inn is a delightful abode for travelers looking to soak up the sun, surf to their heart’s content, and unwind in the peaceful ambiance of a rustic-chic retreat.
To book, check prices or availability for the Hamlet Inn
7. The Chequit – an elegant and chic upscale hotel close to the beach and local amenities
The estate has undergone extensive renovations to retain the classic structure with impressive modern upgrades and contemporary comforts.
Guests can choose their accommodation from 36 beautifully decorated and comfortable rooms decked with modern appliances, fine linens, king-sized luxury brands, high-end toiletries, HVAC systems, sound-proofed windows, and TV with streaming services.
The Chequit offers a quintessential bread-and-breakfast experience with a courteous hotel staff commended for their keen attention to detail. Travelers staying at Chequit enjoy easy access to Greenport, Dering Harbor, the local village, and the beach.
To book, check prices or availability for the Chequit.
8. Topping Rose House- an upscale historic hotel with elegant suites and farm to table fine dining
One of the most iconic historic hotels to rejoice in the quintessential Hamptons experience, the Topping Rose House stands unparalleled with its full-service luxury accommodations.
Housed in a 19th-century estate, the Topping Rose House is a magnificent abode blending classic architecture with contemporary comforts and modern design.
Topping Rose is home to 6 elegantly decorated one-bedroom suites and 16 lavish guest rooms, featuring high-end linens and bedding from celebrated American brands and organic bath amenities.
The cool hotel’s onsite Jean-Georges restaurant is the ultimate spot to feast on local flavors with an impressive farm-to-table dining experience.
Guests can also enjoy the hotel’s serene lap pool, a historic barn that serves as an event space, and the luxury shuttle service to explore the area’s fabulous beaches.
To book, check prices or availability for Topping Rose House.
9. Sunset Beach Montauk- a cool, contemporary beachside hotel with stunning views ideal for watersports enthusiasts
Nestled 100-steps away from the white sandy shores of Sunset Beach, the Sunset Beach Montauk has an idyllic setting, with sprawling views of the waterfront and the Montauk Harbor.
The location of this boutique hotel is more than ideal for travelers who want to enjoy the ocean, embark on jet skiing adventures, and lounge around to soak up the Montauk sun with live entertainment.
The guest rooms and suites have been decorated with a delightful nautical vibe and a traditional Montauk setting, with sweeping views of the park, waterfront, and harbor. The hotel is also home to the lovely Green Activity Park, sprawling over 3+ acres of unfiltered wilderness.
To book, check prices or availability for Sunset Beach Montauk.
10. The Inn Spot- chic waterfront bungalows that offer breathtaking views of the ocean
The hotel provides a collection of waterfront bungalows featuring fully equipped kitchenettes, Brooklinen bedding, and sprawling patios with delightful views of the waterfront, Ponquogue Beach, and Shinnecock Bay.
The Inn Spot has a whimsical Mexican-inspired appeal, blended with a nautical and surf-inspired theme that will transport you to Puerto Escondido or Santa Teresa. The hotel’s onsite restaurant, Crash Cantina, serves classic Latin American cuisine in a lovely open-air setting.
The Inn Spot is the ultimate destination to plan waterfront weddings, corporate retreats, and beachside parties.
To book, check prices or availability for the Inn Spot.
11. Capri Southampton- a chic and elegant beachside hotel with lavish upscale amenities
The Capri Southampton offers 29 elegantly decorated, lavish rooms and suites with sprawling views of the beach and nearby attractions. The rooms are decked with contemporary comforts, luxury bedding and linens, and ample privacy for an unforgettable experience.
Home to the famous Bathing Club, Capri’s poolside retreat is a heavenly spot to unwind, relax and soak up some vitamin D in the verdant setting of the hotel’s gardens.
The newly opened in-house restaurant, Capri X NAIA, combines a beachside setting with delicious cuisine and flavorful cocktails.
To book, check prices or availability for the Capri Southampton.
12. Journey East Hampton – a cool, trendy, and secluded oasis with easy access to oceanfront amenities
Guests can choose from 22 elegantly furnished guestrooms and 3 sprawling cottages that combine privacy and seclusion with a romantic blend.
Journey offers easy access to the bay beaches, oceanfront, local restaurants, and some of the most celebrated wineries in South Fork.
Guests can splash around in the hotel’s saltwater swimming pool or have picnics on the verdant lawn. This hidden gem is ideal for travelers craving peace and seclusion and vacationers eager to immerse themselves in a lively beachside retreat.
To book, check prices or availability for Journey East Hampton.
13. The Shoals Suites & Slips- a cool, contemporary, and chic hotel ideal for those on the winery trail
The ideal location will position you in the heart of all the beachside fun and action, as the Shoals is within proximity to some of Southold’s most prestigious wineries, beautiful beaches, fine dining establishments, and the breathtaking marina.
Designed as a comfortable home away from home, this dockside hotel offers luxurious and spacious suites, featuring a fully-equipped kitchen, state-of-the-art appliances, and lavishly comfortable bedding.
The hotel’s proximity to the charming village of Greenport makes it perfect for travelers looking to attend iconic festivals or embark on the world-famous Long Island Wine Trail.
To book, check prices or availability for the Shoals Suites & Slips.
14. The Pridwin Hotel- a cool and contemporary beachside hotel perfect for a rejuvenating retreat
The resort is home to 49 lavishly comfortable guestrooms and 16 private cottages with breathtaking views of the waterfront and bay.
The Pridwin offers a magical setting to immerse yourself in the splashing waves, white sand, verdant gardens, and dreamy wooden architecture.
The interiors have a charming appeal with a whimsical wooden façade, grand living spaces, and lovely waterfront views from the veranda.
Guests can enjoy rejuvenating massages and beauty treatments at the world-class spa and fine dining evenings at the hotel’s iconic restaurant.
To book, check prices or availability for the Pridwin Hotel.
15. The Hermitage at Napeague- a cool oceanfront oasis perfect for watersports enthusiasts
Tucked in the breathtaking dunes of Amagansett with a magnificent oceanfront structure, the location couldn’t be more ideal for travelers eager to indulge in surfing, sun-soaking, and beachside fun.
The Hermitage offers beautifully furnished two-bedroom suites and units featuring a fully functional kitchen, a TV with cable services, a living room, and a dining area.
The residential units have been elegantly decorated with luxuriously comfortable sleeping stations and remarkable attention to detail. Guests at this trendy hotel have access to private decks and two state-of-the-art tennis courts.
To book, check prices or availability for the Hermitage at Napeague.
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Ever since he was knee-high to a grasshopper Michael has always been a sucker for an adventure. Growing up he was lucky enough to live in a handful of exotic far flung locations including Hong Kong, Pakistan, Kenya and Tanzania and since then he’s continued his taste for seeking out new cultures. So much in fact he now travels the world as a trading digital nomad, exploring everything from the sizzling street markets in Bangkok to random back alleys in Sri Lanka and everything in between! He also has a special fondness for Cohibas, street food, playing carrom, and fine wine and knows his clarets from his chiantis. He counts Cuba, Amsterdam, Indonesia, Cambodia and Italy as his favourite destinations.