Most Romantic Hotels in Long Island

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From a spectacular French-chateau-style property (the top wedding venue in the country, as a matter of fact) to a peaceful beachfront hotel with a shaker shingled exterior and blue-and-white awnings, these are the most romantic hotels in Long Island.

  1. Oheka Castle, built in the 1920s as the second largest private residence in the U.S., is a magnificent chateau-style property on the highest point in Long Island. It’s one of the most striking properties on the East Coast, and the top wedding venue in the country. Thirty-two individually decorated rooms come with elegant furnishings and upscale amenities, and stately common spaces include a grand sun-drenched library, a fine-dining restaurant, and 23 acres of striking manicured gardens, filled with reflecting pools and statues.

  2. Gurney's Montauk is a stand-out property for its beachfront location, one of the best spots in the Hamptons. The upscale hotel is right on a truly fantastic and massive stretch of sand, and its location, size, and layout affords sweeping ocean views from nearly every point on the property. Gurney's is also distinctive among Montauk resorts for its many features: it has a full-service spa with indoor pool, Roman baths, and steam rooms; a big fitness center; a fine-dining restaurant with fresh seafood and ocean views; and lots of event space. Ongoing renovations have made (most of) the 109 rooms contemporary and attractive, and many have stunning ocean views from private verandas. 

  3. A short walk from the village of East Hampton, The Maidstone is a historic, 19-room cottage property that appeals to stylish Manhattanites. Rooms tend to be on the smaller side, while suites offer a seating area and a bit more space. Three private cottages are separate from the main building and have their own entrances, as well as wood-burning fireplaces and private blue-stone patios. All rooms feature amenities like organic cotton linens, towels, and bathrobes; aromatherapy burners and essential oils; French presses and organic coffee; and minibars stocked with local and organic treats. The on-site restaurant and lounge -- open for brunch, lunch, and dinner -- is considered a hot spot in East Hampton. Its kitchen uses organic ingredients from the garden out back or from local producers, and the wine cellar holds hundreds of selections from around the world.

  4. Mill House Inn is a centuries-old historic home just steps from the village of East Hampton. The owners, Gary and Sylvia, offer outstanding services, including free breakfasts served in the lovely dining room or rose garden and a variety of gourmet refreshments, fresh cookies, and charcuterie plates available around the clock. The 10 rooms and suites are individually decorated and feature gas fireplaces, Italian linens, and modern and spacious bathrooms with soaking tubs. The location is not directly on the beach and rooms come at a high price, but the top-notch breakfast and easy walk to restaurants and shops make it a stand-out option. Travelers in want of chic and modern style and a romantic on-site restaurant might prefer The Maidstone.

  5. This American Tudor-style hotel in Montauk is a summer hot spot that maintains an essence of “cool” without pretension. The 67 rooms and suites have a surf-chic vibe and appeal to the Manhattan set with amenities such as high-quality linens and Aveda products. Though not directly on the beach, expansive grounds include lawn games, daybeds, hammocks and an organic restaurant and bar. The outdoor pool -- with live music on weekends -- is popular, and the party scene has been known to carry on until the wee hours of the morning.

  6. The Montauk Beach House is a small, four-pearl boutique hotel with 33 rooms, known for its lively party scene. Though it doesn’t have a beachside location, the two outdoor pools are the central hub of the property -- this is where guests congregate not only to swim and sunbathe, but also to mingle and kick up their heels during the Saturday night pool parties featuring a live DJ. The spacious guest rooms have trendy decor with funky vintage touches like wrought-iron beds, claw-foot bathtubs, and Edison lamps. 

  7. A four-generation family business, the Hampton Maid is a charming mid-range property on a hillside overlooking Shinnecock Bay. The 29 cottage-style rooms are bright and clean with individualized decor, wooden decks, and sleek mini-fridges. Locals and guests flock to the on-site restaurant for its farm-fresh, made-to-order breakfast, though it's not included with rates. Other features include a lovely, tree-lined outdoor pool, five acres of lawn space, a small playground, and a gift shop selling beach-themed home decor and bath products. While conveniently located for exploring the surrounding Hamptons area, this property might not be ideal for those who want direct or walkable access to the beach. There are occasional bug sightings due to the natural setting at this seasonal property. 

  8. This condo beach property has 32 units in a two-story, motel-style building, surrounded by flower boxes, and property high points include the outdoor pool, private beach access, and location within walking distance of the hamlet of Amagansett. All units come with a kitchen, though they range in modernity and decor (with some pushing the dated-and-dowdy limits, and others crossing the line of colorful contemporary). If private Amagansett beachfront is what you want, Ocean Dunes is your only bet.

  9. This charming East Hampton inn is a cozy gem. Built in 1870, it still retains its original Victorian charm while also offering modern comforts such as free Wi-Fi, contemporary bathrooms, and flat-screen TVs. With a total of 12 unique rooms, decorated mostly in calming and seaside-appropriate whites and blues, this hotel has several inviting common spaces, including a sunny breakfast room/bar and a bright den area with a computer and jars of sweet treats. A perfectly manicured garden has an expansive terrace and the lobby has a fireplace. The homemade free daily breakfast is creative and top-notch, served with pride by the caring staff. 

  10. Nestled on a quiet stretch of sand in Montauk, Driftwood on the Ocean has 52 privately owned condo units. The Studios and One- and Two-Bedroom Suites at this mid-range property range from pleasant beach-cottage decor to dated-looking units whose furnishings have seen better days. All have kitchenettes or kitchens, and some have patios or decks that overlook the ocean. The well-maintained grounds include barbecue grills, picnic tables, playgrounds, basketball and tennis courts, shuffleboards, and a large pool. The property, which has a front desk and operates like a hotel, also has a fitness center and communal lounge, but there’s no on-site restaurant, which is not uncommon in the area. 

  11. There are 92 individually decorated units at this three-pearl Montauk property, one of the most popular vacation spots in town. The peaceful location on eight-and-a-half natural acres has direct beach access, and is only a five-minute walk to all the shops and restaurants of downtown Montauk. The One- and Two-Bedroom Townhouses have two floors with kitchens and separate bedrooms, plus private decks. On-site, there’s a pool, fitness center, and tennis courts. Wi-Fi is free throughout the property. 

  12. There are 88 individually decorated rooms at this three-pearl Montauk property. Many guests come back time and time again for a peaceful vacation, as the resort is in a quiet area that's a 15-minute walk from downtown Montauk, with a beautiful beach just across the street. All rooms have air-conditioning, a full kitchen, living area, and balcony offering the sights and sounds of the ocean -- several multi-room apartments are also available. The hotel has a heated pool, tennis court, sauna, and free Wi-Fi (although the signal can be spotty), but there is not on-site dining.

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