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A welcome sign for the village of Southampton, established in 1640, with a cyclist on the road.

Southampton Vacation Rentals

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    Check prices for these dates

    Check prices for these dates, December 13–14, 2026

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    Our top choices for Southampton vacation homes

    1. Minutes from the beach, brand new 3 bedroom

    A modern living room with a sofa, armchairs, a coffee table, and a TV.

    2. Minutes from the beach, brand new 4 bedroom

    A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

    3. Newly Renovated Pristine Southampton Colonial

    A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

    4. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

    A wooden gate partially covered by lush green ivy.

    5. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

    A wooden house with a front porch, white railings, and a double door.

    6. Beachfront Jacuzzi All Year - Black Swan Home

    A modern building with large windows overlooking a beach.

    7. Jacuzzi year-round - Villa Luz Private Home

    A residential property with a covered patio, outdoor seating, and a hot tub.

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

    A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

    9. Immaculate Waterfront 2 bedroom!

    A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

    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. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

    A kitchen with a central island, white cabinetry, and a brick accent wall.

    12. The SandPiper

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

    13. Aqua Vista

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

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

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

    15. Spacious 5-bedroom house with Private Beach and Wide Open Bay Views

    A modern living room with a television, a glass coffee table, and a view of the sea.

    16. Beach Block Hideaway

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

    17. Elegant 5-Bedroom Hamptons Home with Private Pool

    A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

    18. American Beech in Greenport - Petite King Room 7

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

    19. Lovely & Spacious Sag Harbor escape with heated pool

    A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

    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 Southampton

    Pristine beaches stretch for miles along this Hamptons gem where celebrities and locals mingle at waterfront seafood spots. Explore historic mansions and boutique shops in the village, then catch a spectacular sunset from Cooper's Beach with a local lobster roll.

    See all hotels in Southampton

    A welcome sign for the village of Southampton, established in 1640, with a cyclist on the road.

    Top reviews in Southampton

    Canoe Place Inn and Cottages

    A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.

    The 1770 House Restaurant & Inn

    An outdoor dining area with trees and tables under string lights.

    Seven Beach Lane

    A modern two-story building with a pool area featuring sun loungers and umbrellas.

    Bridgehampton Inn

    A dining area with a fireplace, bookshelves, and a view of the bar area.

    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 Penny Lane

    A conservatory with a sofa, chairs, a small table, and a view of houses.

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