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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.

Queen Room Cristy’s Madison #5

Smaller room with queen bed. Private bathroom, free cable/Roku, WiFi and beach access. We are a one minute walk from 2 beaches, and minutes from center of town, shopping and various weekly town events. Common area with coffee and water, downstairs is a full restaurant with breakfast, lunch and dinner. Maid service not provided. THIS ROOM IS LOCATED ABOVE A RESTAURANT AND BAR ON THE 2ND FLOOR, ACCESSIBLE BY STAIRS. THERE IS POTENTIAL FOR NOISE, ESPECIALLY ON THE WEEKENDS.

Hampton Bays Hotel, King Suite - 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.

Old Bakery Inn 2 Bedroom Suite. Pet Friendly

RECENTLY UPDATED! The Old Bakery Inn 2 bedroom suite features 1 King bedroom and 1 Queen bedroom with 1 bathroom. New plush bedding, pillows and duvets. Coastal decor and updated TV's and other amenities. Private deck with afternoon sun or enjoy views of Old Harbor from waterfront balcony. Watch the ferries come and go. Located in the heart of downtown and walking distance to the shops, restaurants, bars and beaches. Beach chairs and towels provided, pet friendly.

Offshore - Dune King

Experience exquisite comfort and elegant design in the heart of Montauk. This beautifully renovated property offers breathtaking Dune views, a pool deck, on-site parking and just a block from the beach. Each room is thoughtfully curated with plush king-sized beds, high-thread-count linens, and bespoke coastal-inspired furnishings. Soft neutral tones and natural textures create a serene escape, while style bathrooms with rainfall showers add a touch of indulgence.

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.

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!

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.

Penthouse Bungalow with Oceanview

Enjoy this Penthouse Unit located at the Breakers at Montauk featuring a king sized bed, kitchenette, oversized and luxurious bathroom, on-site pool, private walk to the ocean, walk to Downtown and much more!