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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, 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 wooden patio with a table and chairs, an umbrella, and a white fence.

    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 rectangular swimming pool with lounge chairs and umbrellas, surrounded by a well-maintained lawn and trees.

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

    A backyard with a swimming pool, lounge chairs, and a barbecue area.

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

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

    A beach with sand dunes and a wooden bench.

    9. Immaculate Waterfront 2 bedroom!

    A patio area with two chairs and a table, surrounded by potted plants and a small shed with glass doors.

    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 backyard patio with outdoor furniture, a large umbrella, and a stone fireplace.

    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

    Property grounds

    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 beach with a seagull standing on the sand, waves crashing onto the shore, and a clear sky with some clouds.

    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 backyard with a swimming pool, outdoor furniture, and a fenced area.

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

    The 1770 House Restaurant & Inn

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

    Seven Beach Lane

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

    Bridgehampton Inn

    A long outdoor dining table set with white tablecloths, sunflowers, and clear glassware.

    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 beach with sand dunes and a clear view of the ocean.

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