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Holiday Rentals in Southold, NY

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    ₹ 24,561 Average
    ₹ 67,000+
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    Travellers to Southold are booking September dates now. Secure your holiday home today, and have the perfect trip.
    1 / 25
    5 of 5 stars (14) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 11
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 19
    5 of 5 stars (4) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Central Heating
    • Balcony
    • Grill
    • Washer
    • Terrace
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    3 bedrooms, 2 1/2 baths, sleeps 6 private Pristine, year round, vacation getaway, within 5 minute walk to two white, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home.... View all property information
    Location Information
    Southold, North Fork 11971
    5 of 5 stars Reviewed 25 September 2015
    We had a wonderful time at Hickory House. The location in Southold is perfect for visiting the beach, wineries and farmers markets as well as Greenport and Mattituck. The home...
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    1 / 19
    5 of 5 stars (9) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Grill
    • Porch
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This charming farmhouse is just what you’ve been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy,... View all property information
    Location Information
    Southold, North Fork 11971
    5 of 5 stars Reviewed 2 July 2015
    My husband and I just stayed in this beautiful house with two friends who are a couple. The photos of the house on this site are accurate and, for once, we were not at all...
    5 of 5 stars Reviewed 18 August 2013
    This is a beautiful, well maintained house· Decorated and furnished to a very high standard. Fantastically situated for the beach in the lovely town of Southold. We used for our...
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    1 / 5
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • Grill
    • Air Conditioning
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    • Washer
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This Home is located minutes from beautiful Long Island sound beaches, wineries, and historic Greenport village. Whether you enjoy the sun or antiquing everything is hereby. The house was built in 2009, having all modern conveniences but still holding the North Fork charm. The home has a central... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Parking
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Our immaculate waterview beach house is located in a beach and boating community in Southold, New York, only a mile from the historic village of Greenport. It's the perfect place to relax and take in the North Fork's pristine beaches, award-winning wineries, antique shops, art galleries, and... View all property information
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    Southold, North Fork 11971
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    3 Bedrooms 3 Bathroom home for rent. Beautiful landscape and privacy on a full acre with gigantic fenced in backyard with playground. 5 minute walk or 1 minute drive to private community Peconic Bay beach. Excellent condition and comfort. Weber Grill, sun filled deck , quality entertainment system.... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
    • DVD Player
    • Waterfront
    • Parking
    • Grill
    • Hot Tub
    • Wi-Fi
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This unique country cottage is situated on a spring-fed fresh water lake one block from Kenney's Beach - a sandy Long Island Sound beach staffed by Southold Town lifeguards. Designed to maximize the beauty of its pristine surroundings, the entire back of the house has French doors opening onto a... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 18
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • Ocean Views
    • Porch
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Escape to this idyllic beachfront located directly on the Sound in Southold NY, only 1 hour 45 minutes from NYC. Open-air, camp-style rooms are part of the house's simple charm. Linger over meals with family and friends on the screened-in porch, watch mesmerizing sunsets, swim in the salt water,... View all property information
    Location Information
    Southold, North Fork 11971
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    1 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
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    Amenities & Details
    • Waterfront
    • Balcony
    • Wi-Fi
    • Ocean Views
    • Washer
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    This charming cedar shingled beach cottage is located 45 feet from Long Island Sound with steps leading down to its own private beach. The cottage is surrounded by a wood deck perfect for watching spectacular sunsets...each night, a unique palette of pink, blue and violet sky as the sun drops into... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 34
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Waterfront
    • Parking
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Newly renovated with two new full bathrooms, new kitchen and second floor bedroom/family room with glorious views overlooking the Long Island Sound, the Shorecrest Beach House has never looked so good! The Shorecrest beach house is located on a grassy bluff overlooking the ocean and available for... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Families will love the location of this two bedroom spacious country home just a short walk to a private sandy Shelter Bay beach along a quiet country dead end road, so no through traffic and safe for bicycling, children and walking the family pet. We are glad to be able to welcome your dog, as we... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Shared Garden
    • Outdoor Dining Area
    • Satellite TV
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Parking
    • Patio
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Grill
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and handicapped accessible throughout with wrap around deck, extra wide doorways, new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Parking
    • Porch
    • DVD Player
    • Patio
    • Grill
    • Air Conditioning
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This charming summer cottage is unique in the sense that it is located in the private community of Reydon Shores, and is just walking distance to a private beach and marina. The special feature is its wrap around enclosed porch with a view of the Peconic Bay. If you enjoy the peaceful country... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable... View all property information
    Location Information
    Southold, North Fork 11971
    5 of 5 stars Reviewed 4 May 2015
    An absolutely stunning and beautiful home. Clean, comfortable, fully updated, this house is perfect for peace and relaxation. The bright and spacious sun room is perfect for...
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    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Parking
    • Grill
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse features lots of sunlight, a stainless steel kitchen, all wooden floors, jacuzzi bathtub, mudroom, washer/dryer, wifi, cable tv, air conditioning and... View all property information
    Location Information
    Southold, North Fork 11971