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A pebbled beach at sunset with the sun setting over the horizon.

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    Check prices for these dates, 13 – 14 December 2026

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    Our top choices for Greenport holiday homes

    1. The SandPiper

    A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

    2. Aqua Vista

    A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

    3. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

    A beach with people relaxing, a pier extending into the water, and a clear sky.

    4. American Beech in Greenport - Petite King Room 7

    An outdoor dining area with hanging lights, palm trees, and a bar.

    5. Beach Block Hideaway

    A wooden pathway leading to a beach with scattered rocks and greenery.

    6. Northfork Townhouse walk to all

    A modern dining area with a wooden table, white chairs, and a chandelier.

    7. Renovated Townhouse walk to all

    A modern kitchen with a marble island, pendant lights, and a patterned backsplash.

    8. Beachfront Greenport Villa

    A wooden deck with two Adirondack chairs and a fire pit, overlooking a beach at sunset.

    9. American Beech in Greenport - Deluxe King 6

    An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

    10. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

    A house with a sliding glass door, a white door, and a small porch with potted plants.

    11. Beachfront Jacuzzi All Year - Black Swan Home

    A modern building with large windows overlooking a beach.

    12. Jacuzzi year-round - Villa Luz Private Home

    A house with a swimming pool, surrounded by trees and a fenced yard.

    13. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

    A covered outdoor seating area with a wicker sofa and a coffee table, surrounded by greenery.

    14. NEW private studio 1.1 miles to beach in East Lyme

    A cozy living room with a sofa, a coffee table, and a dining area with chairs.

    15. The Bay Cottage · Rocky Neck Park, Beach & Niantic

    A tranquil beach with stunning ocean views.

    16. Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

    A living room with a fireplace, a grey armchair, and a large window.

    17. Beachside Bliss w/ Game Room, Gym & Golf Green

    A beach with clear skies and calm water.

    18. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

    A beach with sand dunes and a wooden bench.

    19. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

    A porch with a blue door, white columns, and a stone floor.

    20. Luxury Village Rental in the Heart of Sag Harbor

    A two-story house with a gravel driveway and a parked car.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Greenport

    This charming maritime village boasts a historic carousel and waterfront restaurants serving the freshest local oysters. Rent bikes to explore nearby wineries or hop the ferry to Shelter Island for beaches locals recommend when the summer crowds thin.

    See all hotels in Greenport

    A pebbled beach at sunset with the sun setting over the horizon.

    Top reviews in Greenport

    The Homestead

    A beach with houses in the background and a rainbow in the sky.

    Inn at Harbor Hill Marina

    A two-story house with a porch, multiple windows, and a well-maintained lawn.

    The Captain Stannard

    A living room with a stone fireplace, grey sofas, and a coffee table.

    Westbrook Inn B&B

    A patio with Adirondack chairs, a fire pit, and a view of a lake.

    The 1770 House Restaurant & Inn

    A large, two-story house with a well-maintained garden and a pathway leading to the entrance.

    Canoe Place Inn and Cottages

    A large, two-story house with a prominent front porch and a stone retaining wall.

    The Roundtree, Amagansett

    A small, white door with a wooden exterior, a small porch, and a mailbox.

    The Menhaden

    A two-story building with large windows, a sign reading "The Menhaden," and bicycles parked outside.

    The Bentley Hotel Southampton

    A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

    Marina Bay Cottages

    A white wooden house with a blue door, a small porch, and a white railing.

    The Shoals Suites and Slips

    A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

    The Hampton Maid

    A two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.