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Maidstone Estate Hotel Owner Hamptons Private Loft

Style -Photo Art - Design - 300 square ft in size. Stay in an upscale loft that’s near everything you want to visit. This luxury loft is set back from the magical Maidstone Hotel. This is the owners loft with all the privileges and more. Just steps away from the owners homes lies this stylish loft. Best kept secret in East Hampton. Steps away from the hotel or use the side entrance with private parking to be invisible. Close to town , close to the beach. Private pool. Pets Loft /private bathroom

Superior Queen Guestroom

Bespoke suites boasting modern amenities, land marked distinction and luxe charm. A designated landmark hotel and restaurant are the embodiment of 18th century seaside charm-Located in the most coveted location in the Hamptons. Room features Free WiFi, Free Local Calls, Telephone, TV, Room Services, Minibar, Coffeemaker, Wake up calls, Private Bathroom, Self Controlled AC/Heating, Alarm Clock, Hairdryer, Iron/Ironing Board. This is a Non Smoking Room. Max Occupancy of 2 guests per Guestroom.

Beachy-chic retreat with signature awning stripes

Located directly across the vibrant pool scene at the hotel's Bathing Club, each Club Double offers guests a refreshing blend of diversion and tranquility. Designed in classic Hamptons style, each room incorporates a chic yellow and white striped color palette with nautical accents. The rooms also feature unique pieces reminiscent of the 1940s and 50s, like framed vintage swimsuits and coffee table books about the history of swimwear. Each Club Double has two double beds.

Hampton Bays Hotel, Bunk Room - Adults Only

Hampton Bays Hotel on Main is a boutique hotel in the heart of town, featuring comfortable, affordable rooms above the Rod and Reel and Bub's Tavern. Enjoy a contactless stay with online check-in and secure smart locks with personalized access codes, designed to ensure guest privacy and convenience. Located close to beaches, dining, and nightlife, our hotel provides a high-quality experience at the center of it all, perfect for exploring the vibrant charm of the Hamptons.

Long Island Sound Views | Free Breakfast & Pool

Wake up to the waves at Sound View Greenport. Every room boasts a private waterfront deck overlooking the Long Island Sound. Unwind on our quarter-mile private beach, lounge by the seasonal pool, or savor local seafood at The Halyard. Just minutes from North Fork wineries and downtown Greenport, this mid-century modern retreat offers the perfect mix of relaxation and adventure. End your day with a cocktail at the Piano Bar and a stunning sunset.

Partial Harbor Views + Free Breakfast & Pool

Wake up to harbor views at The Harbor Front Inn, perfectly set in the heart of Greenport Village. Just steps from Mitchell Park Marina, boutique shops, and the Shelter Island Ferry, this stay blends coastal charm with modern comfort. Enjoy the seasonal outdoor pool, start your mornings with complimentary breakfast, and take advantage of free parking while exploring Long Island Wine Country and the North Fork’s best spots.

Spacious living area, deck & tennis court views

Our Junior One Bedroom Cottage features one bedroom with a queen bed. In the luxurious and spacious living room, there is a wet bar with refrigerator/freezer and is equipped with glassware, flatware, tableware and more. With views of the tennis court, the large private deck adjoins the cottage and features sofas and chairs for lounging and relaxing to complete the perfect escape.

One Bedroom At Boutique Complex Adjacent to Ocean

Enjoy this one bedroom one bathroom unit located at the Plum in Montauk! The unit features a queen sized bed in the private bedroom, a full-sized sleeper sofa, kitchen, complimentary wi-fi, and an outdoor deck. The property features an outdoor heated pool, outdoor shower, daily housekeeping, walk to the beach, and a walk to Downtown MTK!

Roomy Room at tranquil, nature-focused retreat

- Airy guestrooms rock vaulted ceilings and a soothing, nature-inspired vibe, plus mini-fridges and Flamingo Estate toiletries. - Borrowable bikes make it easy to explore the area's oh-so-idyllic country roads, Westhampton's downtown or the beach. - Evenings are best spent by the firepits (ideally with a glass of wine in hand).

Fire Island Escape, Steps to the Beach!

Located at the Seashore Condo Hotel, in Ocean Bay Park, escape to Unit 15. This charming second-floor wood-paneled room is your perfect home base for a relaxing Fire Island getaway. Located by the bay and just moments from the beach, it's ideal for couples or solo travelers looking to unwind by the coast.

Don’t miss the iconic Montauk Lighthouse

Our largest and most spacious accommodation, the Ruschmeyer Suite features a plush king bed, twin bunks, a lounge area, and plenty of room to unwind. It’s the perfect setting for families, longer stays, or guests looking for a little extra breathing room.

Ask about Fireside Chats calendar

The private balcony of this Double Queen room overlooks our lush, natural dune-scape courtyard, and is a breezy walk to the pool and the Atlantic. Features two queen beds perfect for friends or family traveling together.